Over the summer, I had two separate clients reach out to me about Sardinia.

The stunning island off the west coast of Italy is having a moment, and for good reason. It has gained popularity thanks in part to travelers like Stanley Tucci showcasing a side of Italy many Americans haven’t experienced, and access from the U.S. is becoming easier, with Delta announcing a direct flight from JFK to Olbia, the airport that is central to exploring the northern part of the island.

But what really piqued my interest was planning two distinctly different trips: one for a young family with three children under the age of five, and another for a dad traveling with his twin 15-year-old daughters who are adventurous foodies.

Same island. Very different trips.

When I first started researching Sardinia, I was a bit overwhelmed. This isn’t an island where you simply pick a beautiful hotel and figure out the rest when you arrive. It’s much larger and more spread out than I realized, and where you establish your home base has a significant impact on the experience.

While there is plenty to explore throughout Sardinia, I’m going to focus primarily on the northeast area, where both of my clients spent their time and where some of the island’s most iconic beaches, luxury resorts and charming towns are concentrated. This is typically where most first time visitors establish their home base and focus for their holiday.

First, a Little About Sardinia

A shepherd showing how to make cheese.

Sardinia is Italian, but it has a very distinct identity of its own.

Its geographic isolation has helped preserve traditions, food, language and a strong shepherding culture that can feel worlds away from mainland Italy. Move inland from the glamorous coastline and you’ll find the shepherding communities, small villages, and a way of life that has remained remarkably connected to the land.

It’s also home to one of the world’s original Blue Zones, regions identified for having unusually high concentrations of people who live exceptionally long, healthy lives, often well into their 90s or even becoming centenarians. In Sardinia, the actual longevity region is concentrated in the mountainous east-central part of the island, not along the Costa Smeralda. Researchers have studied why so many people here live such long lives, looking at everything from genetics and diet to daily movement, strong social, family and faith connections, and the island’s traditional shepherding lifestyle.

That contrast is one of the things I find most interesting about Sardinia. You can spend one day surrounded by superyachts and beautiful beach clubs and another learning about a centuries-old way of life, making cheese and meeting baby sheep.

Getting There and Getting Around

For the northeast, Olbia is the airport you want. From there, many of the best-known resorts and Costa Smeralda are within relatively easy reach.

But here’s something I learned quickly while planning these trips: rent a car.

Sardinia isn’t a destination where I’d rely on taxis or expect to walk everywhere. Having a car gives you the freedom to explore the beaches, small towns and restaurants that make the island so interesting.

Just bring some patience.

Parking near popular beaches and towns can be challenging during peak season, and distances that look short on a map don’t always translate into quick drives. Sardinia rewards travelers who don’t try to cram too much into a day.

Where to Base Yourself

This is always one of the biggest decisions I work through with clients, and in Sardinia, these two families ultimately chose very different approaches.

My young family opted for Airbnb-style accommodations, which gave them the space, laundry, kitchen and flexibility that can be invaluable when traveling with three children under five. Rather than making the hotel the centerpiece of the trip, they had a comfortable home base and used their rental car to explore the beaches, towns and experiences around them.

But where you establish that home base matters. Northeast Sardinia has several distinct areas, and each offers a different experience.

Santa Teresa Gallura: For Beaches and Sunsets

At the northern tip of Sardinia, Santa Teresa Gallura offers a more relaxed home base, with beautiful beaches, dramatic granite coastline and some spectacular sunsets. The town itself has restaurants, shops and a lively center, but without the polish or see-and-be-seen atmosphere of Porto Cervo.

This is also where my other family stayed at Valle dell’Erica, a resort I was initially drawn to because it offered a lot of value compared with some of the better-known luxury properties along the Costa Smeralda.

They came back raving about it.

The rooms were spacious, the spa was excellent, they enjoyed the variety of on-site dining, and perhaps most importantly, they thought the concierge team was fantastic. Their overall assessment was that the resort punched well above its weight, which is exactly the kind of client feedback I love receiving. It doesn’t always have to be the most expensive or famous hotel to deliver the best experience.

Porto Cervo & the Costa Smeralda: For the Glamour

If your vision of Sardinia involves superyachts, beautiful people, designer boutiques and a little see-and-be-seen energy, this is where you’ll find it.

Porto Cervo was purposefully developed as a luxury resort destination in the 1960s, when Prince Karim Aga Khan IV and a group of investors saw the potential in this then largely untouched stretch of Sardinia’s northeast coast. Today, its Piazzetta and marina remain the center of the action, surrounded by boutiques, restaurants, galleries and some truly impressive yachts.

This is also where you’ll find some of Sardinia’s most iconic luxury hotels.

Hotel Cala di Volpe, part of Marriott’s Luxury Collection, is the grande dame, with its distinctive 1960s architecture, sprawling saltwater pool, beautiful bay and a dining scene that includes everything from its famous poolside Barbecue to Matsuhisa. This is the choice for someone who wants the full glamorous Costa Smeralda experience.

Romazzino, A Belmond Hotel has a more secluded beach-resort feel while still putting you within easy reach of Porto Cervo. I’d consider it for someone who wants the service and polish of this part of Sardinia without necessarily needing to be in the middle of the scene every evening.

Hotel Pitrizza is smaller and more discreet, with villas tucked into the landscape and a private beach. This would be my pick for travelers who want Costa Smeralda luxury but value privacy over buzz.

Cervo Hotel puts you right in Porto Cervo itself. You’re steps from the Piazzetta, restaurants, shopping and evening activity rather than retreating to a resort farther along the coast.

But I wouldn’t choose Porto Cervo simply for the hotels.

Spend an evening wandering the Piazzetta and marina, have an aperitivo while yacht-watching, browse the boutiques and galleries, or make a night of dinner and drinks. During the summer, Porto Cervo also has a rotating calendar of concerts, cultural events and nightlife.

By day, explore the surrounding beaches, reserve a beach club, or play a round at Pevero Golf Club.

San Pantaleo: For Village Life

Just inland from the Costa Smeralda, San Pantaleo feels like a counterpoint to Porto Cervo. It’s a small village framed by dramatic granite mountains, with cafés, artisan shops and a wonderful Thursday market.

I’d consider this area for someone who wants more of a village atmosphere and a stronger sense of place while still being close enough to dip into the beaches, restaurants and glamour of the Costa Smeralda when they want it.

San Teodoro: For a More Casual Beach Town

South of Olbia, San Teodoro offers yet another version of northeast Sardinia. It’s known for long stretches of white sand and shallow turquoise water, including La Cinta, and has a more casual, lively beach-town atmosphere.

With restaurants, shops and plenty happening in town, it can be a particularly good home base for families or travelers who want beautiful beaches and activity nearby without making a luxury resort the center of their trip.

Regardless of Where You Stay, Get Out on the Water

The Maddalena Archipelago is one experience I’d build into almost any itinerary in northeast Sardinia.

Rent a boat for the day and explore the islands, secluded coves and beaches that are best reached from the water. Swim, stop for lunch and take your time. With some of the clearest turquoise water in the Mediterranean, this is one of those places where the journey really is the activity.

And that’s really the appeal of northeast Sardinia to me. You don’t have to choose between glamorous Sardinia and the more local one. You can stay at a beautiful resort, spend an evening yacht-watching in Porto Cervo, wander a village market the next morning and be swimming off a boat in the Maddalena Archipelago that afternoon.

The trick is choosing the right home base for how you want to experience it.

At the Table

Sardinian food deserves more attention than it gets, and it’s distinctly different from what many of us think of as “Italian food.”

Sardinia’s location in the Mediterranean and centuries of outside influence, including Phoenician, Roman, Spanish and Catalan rule, have left their mark on the island’s cuisine. But its relative isolation also helped preserve a strong shepherding culture and culinary traditions all its own. The result is a fascinating mix of land and sea: pecorino made from sheep’s milk; pane carasau, a paper-thin, crisp flatbread; malloreddus, small ridged pasta traditionally served with sausage and tomato; culurgiones, stuffed pasta typically filled with potato, pecorino and mint; porceddu, slow-roasted suckling pig; incredibly fresh seafood; and seadas, fried pastries filled with cheese and traditionally finished with honey.

And then there’s Cannonau, Sardinia’s local expression of Grenache, which gives me yet another reason to like this island.

Northern Sardinia’s culinary identity is particularly rooted in Gallurese traditions, pristine seafood and exceptional local ingredients. I encouraged my clients to enjoy a few meals at Valle dell’Erica, leave room for leisurely lunches while exploring the Costa Smeralda, and choose two or three destination dinners worth getting in the car for.

At Valle dell’Erica: My clients particularly enjoyed Le Zini, the resort’s beachfront restaurant, where seafood and Mediterranean dishes come with a beautiful view of the water. For traditional Sardinian cuisine, Li Ciusoni is set in the style of a Gallurese farmhouse and focuses on handmade pastas, roasted meats and local cheeses. La Prua is another great choice for seafood, overlooking the Maddalena Archipelago and particularly lovely around sunset.

Around Porto Cervo: Renato Pedrinelli combines a serious wine shop with a restaurant known for fresh seafood, Sardinian ingredients and an excellent wine selection. I Frati Rossi pairs polished Mediterranean cooking with a beautiful terrace overlooking Cala di Volpe. Both are the kind of places where I’d plan a leisurely lunch and leave the afternoon relatively unstructured.

Worth the drive: Millo is a great choice for beautifully prepared seafood without unnecessary fuss, along with a wine list that leans heavily into Sardinia. Capogiro at 7Pines offers a more contemporary interpretation of the island’s ingredients in a beautiful resort setting.

And for a true destination dinner, I’d head to Il Fuoco Sacro at Petra Segreta Resort & Spa near San Pantaleo. The Michelin-starred restaurant showcases Sardinian ingredients through a more refined lens, and I’d make an evening of it: Spend some time wandering San Pantaleo’s galleries and boutiques, stop for an aperitivo, and then head to dinner.

That’s exactly the kind of evening I love building into an itinerary. The restaurant may be the reservation, but what happens around it becomes part of the experience.

Yes. And I really like the private chef addition because it’s not just “here’s another luxury experience.” There’s a practical reason you recommend it, especially for a family staying in a villa or rental. I’d put it first because it solves arrival night beautifully.

What I’d Make Time For

Hire a private chef
This is one of my favorite recommendations for your first night, especially if you’re staying in a villa or Airbnb. You’re jet-lagged, you don’t know where the grocery store is yet, and no one wants to figure out dinner. Have a local chef come in, take care of everything and introduce you to Sardinian cuisine while you unpack, settle in and enjoy a glass of wine. It’s both practical and a wonderful way to start the trip.

Get out on the water
If you’re staying in the northeast, this is one experience I’d prioritize. Charter a boat for the day to explore the Maddalena Archipelago, swim in impossibly clear water and reach coves and beaches that are much easier to experience from the sea. Pack a swimsuit, stop for lunch and make a day of it.

Spend a day at the beach
This sounds obvious, but Sardinia’s beaches really are the headline. Don’t feel like every day needs to be an excursion. Pick a beautiful stretch of sand, arrive early and stay awhile. Just do a little planning beforehand. Some beaches require advance reservations, and parking can fill quickly during the summer.

Go horseback riding
For families or travelers who want to experience the coastline from a different perspective, horseback riding offers an entirely different way to take in Sardinia’s beautiful scenery. I especially like this as a break from another traditional beach day.

Look beyond the Costa Smeralda
One of the experiences I loved discovering while planning was the opportunity to spend time with Sardinian shepherds and learn about the lifestyle associated with the island’s Blue Zone. Experiences can include walking with shepherds, learning about traditional cheesemaking and sharing a meal built around local products.

It’s a long day from the northeast, so I wouldn’t suggest it for every itinerary. But for the right traveler, it offers something the beach clubs simply can’t: a glimpse into the culture that has shaped Sardinia for generations.

When I’d Go

For most of my clients, I’d target late May through June, or the first half of September.

You’ll still have warm weather and plenty of opportunity to enjoy the water, but without the intensity of July and especially August, when Italian and European holiday travel sends demand, pricing and crowds soaring.

If you want the full Costa Smeralda scene, summer certainly delivers it. But if your goal is beautiful beaches, great food and actually being able to explore the island, I’d take the shoulder season.

What Sardinia Taught Me

Before planning these two trips, I mostly associated Sardinia with beautiful beaches and the glamorous Costa Smeralda.

And yes, it absolutely delivers both.

But what I didn’t appreciate was how much exists beyond that coastline: small villages, shepherding traditions, a fascinating food culture, families who have lived on this island for generations and an interior that feels completely removed from the yachts and beach clubs just a few hours away.

Planning Sardinia well isn’t about trying to see the whole island in one trip.

It’s about choosing the right home base, slowing down enough to explore what’s around you, and deciding which version of Sardinia you want to experience.

Or, ideally, finding a way to experience a little bit of both. Reach out if you’d like to learn more about experiencing Sardinia for yourself next summer!

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“I think you have found your calling.”

My former boss reached out to me to plan a joint cruise with a friend and her family.

Of course I wanted to impress her. I wanted to show her that I understood the ship she was sailing on, considerations for cabin selection, packages to purchase in advance, how to structure the itinerary so it wasn’t too busy, and all of the excursions.

Truth be told, I had never worked with this cruise line before, nor had I sailed with them myself. But I had been on several cruises and toured many of the ports on her itinerary.

I used every resource at my disposal. I called the cruise line to ensure the cabin was the right fit, mapped out transfers and structured events, provided dining recommendations, built a customized itinerary in the Fora app, and wished her bon voyage, hoping everything would go according to plan.

When she returned, she said, “I think you have found your calling.”

I can’t imagine a better compliment from someone I worked with for more than a decade, someone who fostered my career in project management, celebrated my successes, and helped me navigate plenty of challenges along the way.

As I reflect on the one-year anniversary of The Curated Course, there are so many ways my business has started to click. I’m figuring out my niche at the intersection of how a client engages with me and where I can provide the most value. I’ve implemented systems that help protect my time and expertise while allowing me to work more efficiently. And I’ve learned many lessons along the way, not just about the industry, but also about myself.

Today’s newsletter is a reflection on those lessons and a glimpse into what I hope the future looks like for The Curated Course.

Why I Started

Some of you may know what the last few years have looked like for me, but there’s been a lot of activity at the Agee household. We made a cross-country move from Chicago in 2022, and then, after being downsized from my corporate job a little over two years ago, I’m not going to lie ... I was a bit lost.

I looked for opportunities in project management leadership, interviewed a bit, joined a golf league, learned Mah Jong, and eventually filled my days managing our first-floor remodel thanks to that a-hole Hurricane Milton.

Then came the loss of my little companion, Simba, who had been with me for nearly one-third of my life.

Looking back, I think losing him gave me the push I needed to finally build something that had been sitting quietly in the back of my mind. The idea really began after our milestone Mediterranean cruise with dear friends, but it wasn’t until I needed something meaningful to pour myself into that The Curated Course truly took shape.

As I turn 50 this year, I don’t feel like I’m starting over. If anything, I feel like everything I’ve done up to this point has prepared me for this chapter.

Restaurant ownership taught me hospitality and how to wear multiple hats in any given day.

Corporate taught me how to manage complex projects, budgets, deadlines, and clients while always thinking several steps ahead.

This business simply lets me use those skills in a way that feels more like me.

It’s the culmination of a lifetime of collecting skills, interests, and experiences that now have a home. Looking back, every chapter had a purpose, even if I couldn’t see it at the time. I love that I’ve found a new career that gives me creative freedom and autonomy, integrates my love of food and wine, and allows me to genuinely help people experience something they might not have otherwise.

What This Year Has Taught Me

“Life Moves Pretty Fast”: Just Start

When I started, I didn’t know exactly what I wanted The Curated Course to become, and I think I’d still be trying to figure it out if I hadn’t simply jumped in.

I leaned heavily on recipes from destinations we had visited, featuring my tips and techniques on how to bring a bit of a faraway town to your own table. It may have been ambitious to think I could create all these recipes because it isn’t as simple as it seems. There are multiple iterations, grocery visits, remaking components or an entire dish, and rarely does it go right the first time.

Then there are all the food samples. I gave away so much as I was trying out new recipes because I hate food waste. As the travel planning picked up, the food blogging had to slow down. One will eventually pay the bills, and the other is more of a hobby.

But those months of trying so many recipes helped me understand the innate relationship between food, travel, and culture. The collaboration with was one of the highlights. She provided me with an authentic Bolognese recipe, and I recreated it stateside. What a treat to be able to share it with my subscribers!

When I started The Curated Course, none of this was on my radar, and that’s been the most exciting part.

In the famous words of Ferris Bueller, “Life moves pretty fast.”

So if there’s something you’ve been contemplating, I’ll simply say this: just start.

No One Knows Everything

I remember returning to corporate after owning and operating our restaurants for six years. My first assignment was to write a “project brief,” which was essentially the same as a job start form, but I had no idea.

I wanted to prove myself so badly that I quietly spent hours trying to figure it out.

Eventually, I realized asking the question would have saved me so much time and frustration. I’ve carried that lesson into this business. Every industry has its own language, and checking your pride at the door accelerates learning.

Through my host agency, Fora, we have what is essentially a giant Slack channel where I can search and ask questions on almost any topic, and other advisors chime in with their experiences or point me toward the right resources. What continues to surprise me is how genuinely helpful everyone is with their own knowledge and experience, which in turn encourages me to share mine.

I now know that my clients don’t expect me to know or have an opinion on everything. What one client desires may be completely different from another. My job is to present the information, share any relevant experiences I may have, and help them envision the experience so they can make an informed decision.

Recently, I’ve been working with a client planning a private catamaran charter in the BVIs over spring break with her 10- and 12-year-old daughters. She asked if she should add time on the front end or back end.

We connected on the phone and talked through the logistics: flying into Tortola, taking a water taxi to Road Town, and either staying at a decent hotel in the area before boarding the catamaran or going straight to the boat. Given the logistics and avoiding another pack/unpack, it was a no-brainer.

After the charter, we decided on a night at a luxury resort because who doesn’t want a real shower after being on a boat for five days!

Point being, this was a new booking type for me, but it didn’t feel new. Before planning the trip, I spoke with an advisor who has booked quite a few BVI charters. And I’ve now walked enough clients through complex itineraries to understand the questions to ask and get a sense of how they want to experience their travels.

Don’t Be Afraid to Build the Bus While You’re Driving It

Develop processes, but know you’re going to be driving the bus while you’re still keeping the wheels on.

Between finding my niche, deciding how to balance food, wine, travel, and this newsletter, starting my company as a new brand, and learning entirely new skills (hello, AI!), there were definitely moments when I got crispy.

I’m a planner and overachiever by nature, and not having those systems in place was very unnerving at the start. There is still a never-ending list of tasks, Google Docs, training webinars, and forms I’d like to automate. I would wake up in the middle of the night excited about everything new that was happening, thinking about what processes I could or should put into place. The enthusiasm and desire to have everything in place when it’s all yours and still so new is real.

But I also didn’t know what I needed. It takes time to understand what the business needs, what clients need, and how to manage a new routine.

Establish Boundaries Early

This is something I’m still learning.

Good clients don’t expect you to work 24/7. They also enjoy a break from their own jobs when it’s time to plan a vacation.

Protecting my time allows me to be more creative, more thoughtful, and ultimately a better advisor.

I’ve also learned that my expertise has value. Whether it’s planning fees, managing expectations, or creating a clear planning process, boundaries aren’t barriers. They allow me to provide a better experience for every client.

Working with me doesn’t mean I get better rates. They’re often comparable to what you’ll find online. But you do get me in your corner when something goes wrong. You don’t want to be on the other side! J/K 🙂

Joking aside, I’m able to research deeply for you, looking not just at the universe of traveler reviews, but also through our own platform and the experiences of advisors whose clients travel like you do. They know what to appreciate in a good property and understand that things aren’t always perfect, but a good team can make all the difference.

I also establish relationships with each hotel, cruise line, tour partner, and in-destination support company before and during your travels to help ensure everything is going as you envisioned.

I may not be for everyone, and that’s okay. I’m learning to be thoughtful about where I invest my time, expertise, and relationships so I can provide the level of service my clients expect.

This Is a Long Game

Being a travel advisor is a long-term effort, not a short game.

If your goal is simply booking hotels, volume can certainly mean dollars.

But that’s not what excites me.

For me, the hotel is just the beginning.

The real magic happens when we build the experiences around it: stargazing over a volcano, lunch at an agriturismo run by generations of the same family, or a sunrise hot air balloon ride celebrating a milestone anniversary.

Very early on, I told myself, it begins with the booking.

Whenever I’m faced with a task I don’t quite know how to tackle, my natural instinct is to procrastinate. I loved the excitement of making the booking, but then I’d think...now what?

The turning point came when Fora introduced a fully integrated itinerary builder. Suddenly, I found myself curating city guides, arranging customized tours, collaborating with local guides, and building complete experiences.

That’s when I realized this was the part of the job I loved most.

Looking Back at Year One

My first bookings were simple: work trips to New York for Don, personal travel for a wedding in Barcelona, and a weekend in New Orleans celebrating a dear friend’s daughter’s 21st birthday.

Then they began to grow, and those early bookings gave me the confidence to plan more complex and nuanced travel experiences.

A multigenerational trip to Italy.

A couple’s road trip through Scotland, their first true vacation in years, celebrating the completion of her veterinary boards.

A pivot to Key West from Puerto Vallarta when violence brought uncertainty to the area.

Even with Don’s work travel, I found opportunities to practice what I hope every client experiences: confirming perks, noting late arrivals, communicating special requests, and making sure everything is in place before the client ever checks in.

Those little touches often prevent much bigger conversations later. I think the anticipatory service I learned from hospitality and the proactivity ingrained in me through project management have really shaped how I help clients plan their travels, including what I can do behind the scenes to ensure everything goes as smoothly as possible.

Looking Ahead

So what’s in store for year two and beyond?

First, some travel of my own to bring you firsthand perspectives on exciting destinations. I’m also exploring more opportunities for group travel, from bringing friends together on an Alaskan cruise or a journey through Japan to women’s retreats and hosted wine trips.

I’ll also continue focusing on the clients I’ve realized are the best fit for how I work: busy professionals.

They value travel. They enjoy the research. They simply don’t have enough hours in the day to do it well.

Finally, I will continue to lean into food and wine, integrating local restaurant recommendations, food tours, and experiences with winemakers I’ve known for years.

After all, I still believe the best way to understand a destination is through its food and wine.

I’m updating my website to better reflect my services, experience, and how I work with clients. More to come on that in the next few weeks!

Thank You

Whether you’ve been here since the beginning, are a client, a fellow advisor, or simply enjoy following along, I’m incredibly grateful you’re here.

One year in, I’m more excited about what’s ahead than what I’ve accomplished so far.

If you’ve enjoyed The Curated Course, I’d love it if you’d leave a comment or tap the heart so others can discover it too.

And if you’re ready to start planning your next adventure, I’d love to help.

Thanks for supporting The Curated Course. Make sure to subscribe so you don’t miss out on any of my upcoming pieces.

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A beautiful display at The Ritz-Carlton Chicago last year.

For all my planners out there, you likely already have your holidays mapped out, and applause to you. 🙂

But if you’re anything like the rest of us, you’re still trying to figure out how to squeeze in one more long weekend before summer is over, let alone whether you’re hosting Thanksgiving, Hanukkah, Christmas, or your annual festive gathering.

As your resident planner, I’m here to tell you that the holiday season has a booking window unlike any other.

In the travel world, we often refer to it as festive season, which is roughly Thanksgiving through New Year’s. It’s when cities put their best decorations forward, Christmas markets and ice skating rinks overtake plazas, and hotels transform their lobbies into destinations all their own. One of my favorite Chicago traditions was spending a Saturday hopping from one beautifully decorated hotel lobby bar to another. Every property tried to outdo the next, and somehow each felt magical in its own way.

It’s also one of my favorite times of year to help clients plan because every family celebrates differently.

Some dream of Christmas markets and midnight Mass in another language. Others want sunshine, a beach chair, and someone else cooking dinner. Some want to gather three generations under one roof. Others are looking for a quiet escape after a busy year.

I love hosting. There’s something incredibly satisfying about setting the table, planning the menu, and welcoming people into your home. But I’ve also learned that traditions don’t have to look the same every year. Some years you have the energy to host. Other years, it’s nice to be the one who’s welcomed. Ironically, experiencing both has made me appreciate each even more.

There’s no “right” holiday destination. There’s only the one that’s right for your family this year.

Why Holiday Travel Books Differently

Unlike summer travel, holiday travel is compressed into a relatively short window. Schools dictate schedules, families often have fixed vacation dates, and everyone is trying to travel at the same time.

That means the first things to disappear aren’t usually flights. The below are the first to go:

• The best room categories

• Connecting rooms for families

• Villas and multi-bedroom accommodations

• Christmas and New Year’s dining reservations

• Ski instructors

• Rental cars

• Private guides and festive experiences

• Premium airline seats and award availability

If you’re traveling with grandparents, multiple families, or have your heart set on one specific hotel, now is the time to start planning. There are only so many adjoining rooms, suites, villas, and holiday experiences available. Miracles can happen, but having options is much more enjoyable than hoping for one.

The good news? Some properties are already offering early booking promotions for the holiday season. Sea Island, for example, recently released a 25% advance booking offer for select accommodations. The earlier you plan, the more likely you are to find both the room you want and the experience you’ve imagined.

Beside, during this Florida heat, doesn’t a crisp snowfall, a mug of mulled wine, and a cozy turtleneck sound at least a little appealing? After many years of delayed or canceled flights to the Midwest, I’m still #teambeach for Christmas!

What Do You Want the Holidays to Feel Like?

One of the first questions I ask clients isn’t, “Where do you want to go?”

It’s, “What do you want the holidays to feel like?”

The answer almost always leads us to the destination.

If your family loves classic holiday traditions ...

Some families want the kind of Christmas they’ve imagined since they were children.

In NYC years ago in front of Rockefeller Center.

New York City remains iconic for good reason. Between the Rockefeller Center tree, Fifth Avenue holiday windows, Bryant Park Winter Village, the Radio City Christmas Spectacular, and beautifully decorated luxury hotels, the city fully embraces the season. So many properties do Christmas well, but standouts from past trips include The Lotte Palace in Midtown, The Ritz-Carlton NoMad, and The Carlyle on the Upper East Side.

In NYC, the festive atmosphere extends far beyond the famous attractions, it is woven into the entire city.

Across the Atlantic, London transforms into one of Europe’s great holiday destinations (cue one of my favorite holiday movies, Love Actually). Regent Street sparkles overhead, Hyde Park transforms into Winter Wonderland with its giant ice rink and holiday attractions, Fortnum & Mason becomes the spot for afternoon tea, Borough Market is dressed for the season, and evenings at the theatre in the West End, it’s a city that truly embraces the holidays.

It’s also one of those destinations where planning ahead matters. Tickets for holiday performances, special events, and festive hotel packages often sell out months in advance.

For travelers drawn to Christmas markets, Strasbourg’s Christmas market has welcomed visitors since the 16th century, filling the historic center with hundreds of wooden chalets selling handmade ornaments, mulled wine, and Alsatian specialties. Vienna offers an entirely different atmosphere, where markets spill across grand squares in front of the Rathaus and Schönbrunn Palace, making it one of Europe’s most elegant festive destinations.

If togetherness matters more than the destination ...

Some of the best holiday trips aren’t about checking landmarks off a list.

They’re about slowing down.

One of my favorite client trips last December wasn’t international at all. Three generations gathered at Sea Island, Georgia, where mornings began with bike rides beneath the live oaks, afternoons were filled with cooking classes and horseback riding lessons, and evenings ended around the fire pits.

They came home talking less about what they did and more about how relaxed everyone felt. Nobody had to host. Nobody had to cook. Everyone simply got to be together.

Other favorites include Blackberry Farm in Tennessee and The Greenbrier in West Virginia, where exceptional hospitality becomes part of the holiday tradition, which needs at least a 12-month lead time.

If you’d rather trade snow boots for sandals ...

For some families, the perfect holiday means sunshine instead of snow.

St. Barths comes alive during festive season, with beautiful villas, exceptional restaurants, beach clubs, and one of the Caribbean’s most celebrated New Year’s weekends. In Nassau, the highlight of festive season is Junkanoo (December 26-31), a vibrant celebration of Bahamian culture with elaborate costumes, live music, dancing, and late-night street parades.

And if complete relaxation is the goal, and you have the time to travel, the Maldives deliver overwater villas, extraordinary service, and festive celebrations without sacrificing tranquility. Resorts like Four Seasons, Patina, and Soneva create elaborate festive programming around the holidays, but their best villas disappear long before December arrives. This is a bucket-list destination and for good reason!

Closer to home, the ABC islands (Aruba, Bonaire and Curacao) offer a unique European feel outside the hurricane belt. They bring in massive Christmas trees, offer caroling, and celebrate Dutch holiday traditions, making them an appealing option anytime but especially during the holiday season.

If your family loves adventure ...

Holiday travel doesn’t have to revolve around decorations.

The Finnish Lapland is one of the few places that can deliver nearly every childhood winter dream at once: glass igloos, husky sledding, reindeer encounters, and the Northern Lights overhead. Most travelers know Santa’s Village in Rovaniemi, but many of the most special properties sit even farther north, where the skies become the main attraction.

Or perhaps this year’s newsletters have convinced you to consider the American West. Luxury ranches, Jackson, Yellowstone, and Big Sky offer a completely different holiday atmosphere with snow-covered mountains, roaring fireplaces, sleigh rides to dinner, skiing, and days spent outdoors together.

If New Year’s is the celebration...

Some destinations truly come alive as the calendar turns.

Edinburgh’s Hogmanay remains one of the world’s most distinctive New Year’s celebrations, blending concerts, torchlight processions, and centuries-old Scottish traditions. Tokyo offers an entirely different energy, balancing city celebrations with meaningful cultural traditions as one year ends and another begins.

Worth Knowing

One of the biggest misconceptions about holiday travel is that booking early is about getting the best price.

More often, it’s about getting the trip you actually want.

The villa that comfortably fits everyone.

The connecting rooms.

The suite you’ve been dreaming about.

The table for Christmas dinner.

Holiday travel is one of the few times each year where availability and not necessarily price becomes the deciding factor.

Looking Ahead

If holiday travel has been on your mind, July is actually one of the best times to start the conversation.

Even if you’re not ready to book tomorrow, talking through your priorities now gives us the flexibility to find the destination that best matches how you want to celebrate.

Whether that’s strolling through a European Christmas market, gathering the family around a table at Sea Island, celebrating Hanukkah somewhere warm, or welcoming the New Year halfway around the world, the memories created during the holidays have a way of becoming the stories families tell for years.

The earlier we begin planning, the more options we have to create the version that feels exactly right for yours.

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Hello friends!

We just got back from a wonderfully restorative weekend with friends on Anna Maria Island. Living in Florida, I’ve learned about incredible access to beach towns and getaways that are less than 90 minutes away from Tampa, a reminder of how much beauty we have so close to home.

Since starting my travel advisory business, I’ve found it surprisingly difficult to disconnect. Between clients traveling and the challenges that inevitably arise, opportunities that pop up unexpectedly, and wanting to share the places I’m experiencing, putting my phone away doesn’t come naturally. This weekend reminded me how important that balance is. In fact, the only photo I took this weekend was of our friends’ pup sleeping with her stuffy.

Frankie enjoying a nap with Sleepy, her stuffy.

Last week’s newsletter was all about family, fresh air, and finding my first dude ranch. This week, we’re continuing our journey through Montana to Wyoming, from Yellowstone National Park to Jackson and Grand Teton National Park.

So often, we board a plane looking for something we think we can’t find domestically. Mountains. Oceans. Charming towns. Incredible food. Outdoor adventure. Genuine hospitality.

This trip reminded me that America has all of those things.

What surprised me most wasn’t just the scenery, although the Tetons are every bit as spectacular as you’ve heard. It was the people. Spending time with the ranch staff, guides, shop owners, restaurant servers, and fellow travelers offered a glimpse into everyday life in a part of the country that felt very different from my own.

Travel has a wonderful way of reminding us that every destination has something to teach us, even the ones in our own backyard.

This week, I’m sharing a few of my favorite moments from Wyoming, including a stunning scenic float down Snake River, why Jackson has earned its reputation as one of the West’s most beloved mountain towns, and the unexpected joy of leaning into Western style.

Through Yellowstone

The Abyss pool, clocking in around 150 degrees Fahrenheit!

The second part of our adventure took us from Big Sky, Montana, to Jackson, Wyoming. Getting there isn’t exactly direct. The best route winds through Yellowstone National Park, which, at any time of year, can present challenges. Wildlife delays, traffic, parking, and unpredictable mountain weather can easily turn what looks like a four-hour drive into a nine or ten-hour day if you stop to experience the park along the way.

To be honest, I really didn’t think I’d care much about Yellowstone. I must have slept through the high school science class that explained what a geological wonder it is. Before this trip, I knew about Old Faithful, but that was about it.

What I didn’t realize is that Yellowstone sits atop one of the world’s largest active volcanic systems. A massive eruption more than 600,000 years ago shaped the landscape we see today, creating geothermal features unlike anywhere else on Earth. Researchers continue to study the park because some of its geology provides clues about conditions on the moon and Mars. I won’t ever be a geologist (sorry to my college bestie!), but after spending a day there, I came away with a much greater appreciation for just how extraordinary this place really is.

We explored Yellowstone with a local guide, and I can’t imagine doing it any other way. She expertly navigated the crowds, but more importantly, she helped us understand why we were looking at what we were seeing. I’ve found that understanding why something is significant almost always makes me appreciate it more.

Norris Geyser Basin

Norris Geyser Basin felt almost otherworldly, with vast mineral fields, steaming vents, and the tallest active geyser in the world, Steamboat Geyser, capable of shooting boiling water 300 to 400 feet into the air during major eruptions. My nephew spent much of the morning carrying an infrared thermometer, excitedly checking the temperatures of the thermal pools. Watching his curiosity grow was almost as much fun as seeing the landscape itself.

One of my favorite things about Yellowstone is how quickly the scenery changes. One moment you’re walking through a geothermal basin that feels like another planet. A few minutes later you’re watching “red dogs,” the nickname for baby bison, grazing alongside their mothers in an open meadow.

We stopped for a picnic lunch overlooking Yellowstone Lake, the largest high-elevation lake in North America, before continuing on to Abyss Pool. Its brilliant sapphire color is almost inviting until you remember the water temperature hovers around 150 degrees!

By late afternoon we left Yellowstone behind and continued south. We stopped several times to admire bison and elk before, almost unexpectedly, the Tetons came into view.

Jackson, WY & The Grand Tetons

Traffic jam with mama bison and a red dog.

The next part of our adventure was spent in beautiful Jackson, WY (Jackson Hole is the name of the resort and broader area, Jackson is the cute little town). We stayed at a beautiful luxury property just outside the town square called Hotel Jackson. My parents had an upgraded suite with 2 balconies, a dining table, and fire pit and even our entry-level rooms were very well appointed with fireplaces, plenty of space and in-room Nespresso makers.

With our same guide we explored the mountains, rivers, Mormon Row (the iconic photo that many associate with the Tetons), Schwabacher Landing, and the wildlife of the Tetons, stopping to look for moose, a traffic jam due to bison crossing, lookout points high above the valleys, and a peaceful picnic along Jackson Lake.

Mormon Row

The Tetons felt completely different from Yellowstone. Aside from the wildlife and lodgepole pines, it was hard to believe we were exploring parks just a couple of hours apart.

The rest of our time in Jackson was much more relaxed, which was welcome after all the activity.

Jackson feels like a town that’s completely comfortable being itself. It isn’t overly polished or trying to be Aspen. People wear boots because they wear boots, not because they’re making a fashion statement. Galleries sit alongside outfitters, and excellent restaurants share the block with Western shops that have been there for decades. It’s walkable, welcoming, and somewhere I could easily spend a few more days.

Lunch at Persephone is a must! It’s an adorable cafe where we ordered pastries and salads, sat outside and enjoyed the crisp mountain air. Drinks at Million Dollar Cowboy Bar where each bar stool is a saddle (I learned how to sit side saddle!), plus an Alvin’s Island equivalent. Any Floridian knows while it’s tough to replicate Alvin’s Island, you can certainly create a sense of place with a store that offers t-shirts and trinkets! While we may have gotten some fun socks at said store, it was a knife store on the corner that caught our eye. More on that in a moment.

Our Favorite: A Float

A majestic bald eagle on the Snake River.

One of the highlights of the trip was the final night. We boarded a recreated vintage wooden boat for a peaceful 90 minute float down the Snake River.

More than one member of my family gets violently seasick and so the prospect of being on a boat for 90 minutes generates a different level of discomfort and fear.

Our guides assured us that they’ve never had anyone experience illness, in fact, they’ve had the contrary … guests have actually fallen asleep! And I can understand why. The tour was conducted at the end of the day so we were the only boats on the river. We weren’t trying to navigate among others, it was truly peaceful.

We saw countless bald eagles and their nests, otters, beavers, osprey, a cattle ranch and then Belgian draft horses greeted us once we got to the dinner site.

A husband and wife team works together to guide the boat tour and do the cooking, with help from a guy who really knew what he was doing on the grill, serving up bison, Copper River salmon and MT Wagyu steaks. We have a dairy allergy in my family and they were so accommodating.

Appetizers were first served around a campfire, with about 45 minutes to explore the working ranch and take photos with a backdrop that didn’t even look real.

Dinner was at a communal table by candlelight and featured grilled portabellas, corn on the cob, sourdough from a local bakery, asparagus and salad. This homemade meal was the perfect end to our trip.

After dinner, we gathered in one of the teepees for dessert which was a light parfait with fresh fruit. All dietary challenges were easily accommodated and it was the perfect end to our trip.

To learn more about the adventure see here.

Bringing a Destination Home

Years ago when my husband and I needed an escape from Chicago winters, we escaped to San Jose del Cabo, the more peaceful side of Cabo, which hosts a weekly Thursday night art walk from November to May. One night while enjoying some wine, we stumbled upon a young artist selling his brother’s paintings on the floor of an art gallery. We were instantly drawn to the vibrant colors of the phoenix and the sweet sibling selling his work. At the time, our condo had a very drab wall and we needed two large pieces to help bring some color and life to the long hallway. These were perfect.

Since then, we’ve gotten more art in Cabo and South Africa, stunning sculptures and vases in North Carolina, handmade steak knives in Crete (out of sheep horns!), a Mah Jong set and a tantalus which is a wooden case that holds whiskey decanters both from antiquing in New Orleans. Every time we look at each of these finds we remember the moments we found them on our travels, and it takes us right back to the destination. It’s not always easy getting them home but well worth the effort.

On this last trip, we were introduced to the most beautiful chef’s knives from New West Knifeworks. These are no lie the sharpest knives I’ve ever used - so much so I barely washed one with a sponge and it sliced it right in half! For years, we’ve had dull knives and for us, the most appealing feature is they offer lifetime sharpening, just ship them back and they’ll give them a good tune up. We got a bread knife for my sourdough, an AP paring knife and a chef’s knife, all made in Idaho.

Given my love of cooking and our hope to find something to remember this trip by, these were the perfect find. We’ll continue adding to them over the years, maybe with or without a trip attached :)

Dressing for the occasion

This trip out west was the perfect excuse to invest in a pair of cowboy boots - I’d been wanting them for some time, as they’re a stylish way to dress up a skirt, wear with jeans, and they were really functional as we navigated the ranch, and even downtown Jackson.

It also happens to be what most locals wear daily. It quickly became clear that Western style isn’t a costume, it’s practical. Boots, denim, hats, and bandanas all have a purpose, something I appreciated even more after spending time on horseback.

When I was researching what to wear for this trip, I was a bit nervous. I didn’t want to come across like I was poking fun at the attire, in fact, far from it! I genuinely wanted to lean in and embrace why certain clothing choices were more appropriate.

After horseback riding, I get it. The soles of your boots need to be able to grip the stirrups, your jeans need to be able to stretch as you get on and off your horse. You want a hat that has a stampede string so it doesn’t go flying off in the wind and spook your horse. You need something to protect the sun on the back of your neck so a bandana is the best way (plus doubles as a handkerchief if you find yourself in a lot of dust).

Aside from the rides, the style is just different and it was so much fun to look at items I already had in my closet to see how they could work out west with a few tweaks…the belt from Amazon that had the right amount of turquoise (and a less than $10 price tag!), a white denim dress that was instantly repurposed with my boots, hat, and bandana from Target, a brown leather jacket that I’ve had for years that was a staple piece during this trip. Yes, I did find a ridiculous dress with horses and cowboys on it from designer Me369. Most of my outfits were things I already had or could easily wear again.

Sitting side saddle!

Thank you for reading all about our wonderful journey. This was truly a trip of a lifetime, and one that I hadn’t had on my radar. We experienced breathtaking national parks, charming towns, warm hospitality, and delicious food, but most importantly, we created memories we’ll be talking about for years.

The sweet spot is likely for kids 8-14, then multi-generational families, couples and girlfriends. Needless to say ... Cowgirl Up 2027 is already on my calendar. If joining me sounds like your kind of adventure, I’d love to tell you more.

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Local Big Sky photographer Kelsey Kradel captured family photos up on the ridge.

My Week Out West: Part I

A week ago, my family returned from a milestone anniversary trip celebrating my parents. Fifteen months in the making, my parents, brother, sister-in-law, nephew, Don and I spent a week exploring Montana and Wyoming, beginning at Lone Mountain Ranch in Big Sky before continuing on to Jackson.

Our family has always traveled well together. Growing up, our adventures took us everywhere from Disney and Hawaii to Branson, Missouri, family reunions, and visits with my grandparents in Arizona. As my brother and I got older, our travels expanded to Germany, Austria, and eventually Italy after our spouses joined the family tradition.

If you ask any of us about those trips today, we probably won’t start by talking about the destination. We’ll laugh about my brother’s infamous combination of red Gatorade and soft serve ice cream that came back up all over yours truly on a road trip (sorry for the visual!), an unbearable heat wave in Austria, bug bites in Germany, my dad insisting we take the subway to a luxury hotel, or the time my mom and I were loudly shushed, “Silence!” during the Glockenspiel in Munich, which only made us laugh harder.

Those stories have become part of our family history, and looking back, I’m incredibly grateful my parents made travel a priority for us. I can see how those experiences shaped my curiosity about the world and, in many ways, led me to the career I have today.

As adults, getting everyone together has become more difficult. When we do, it’s often around holidays where someone is cooking, someone is cleaning, and someone is hosting. Travel changes that. Everyone gets to simply relax and spend time together.

This trip reminded me of that.

Not everyone joined every activity, and that’s exactly how it should be. My parents, brother and I attended Saturday evening Mass in a beautiful little chapel tucked into Big Sky. My dad and I spent one morning throwing axes. My mom and I enjoyed a wonderfully relaxing afternoon at the One&Only Spa. My nephew, brother, husband, dad and I all went horseback riding. Every evening, we found each other again over dinner to share stories from the day.

When we first started planning this anniversary trip, we considered Europe and even a cruise before settling on Montana and Wyoming. None of us had really experienced this part of the country before, and there was something exciting about discovering it together.

There was plenty to love about the American West, so much so that I’m turning this into a two-part series.

This week, I’m taking you to Lone Mountain Ranch in Big Sky, Montana.

Why a Dude Ranch?

Luxury dude ranches have experienced something of a renaissance in recent years. While Yellowstone has certainly fueled the romanticism of the American West, I think there’s something bigger happening. People are looking for experiences that allow them to unplug without completely roughing it, spend more time outside, try something new, enjoy exceptional food, and reconnect with the people they’re traveling with.

I’m not the only one who’s noticed. Publications including Vogue, Condé Nast Traveler, and Architectural Digest have all highlighted the growing appeal of modern ranches, where authentic Western traditions meet refined hospitality.

For us, Lone Mountain Ranch checked every box.

Located just outside Big Sky, it was the perfect starting point before continuing on to Jackson and Grand Teton National Park. The activity roster alone made it an easy decision: horseback riding, hiking, ropes courses, archery, axe throwing, Yellowstone tours, and one of Montana’s best rodeos, all without ever needing to leave the property.

I quickly got used to our morning coffee delivery and a fire.

One of the things I appreciated most about Lone Mountain Ranch was that everyone could experience it differently. Some in our family headed out on trail rides while others hiked, relaxed in lounge chairs with a book, or explored Yellowstone. There wasn’t pressure to do everything, but we certainly took advantage of the ranch’s many offerings each day.

Within a day or two, everyone seemed to settle into the rhythm of ranch life.

The cabins are thoughtfully spaced throughout the property, creating a peaceful sense of privacy. Coffee is delivered to your door each morning with fresh milk, and televisions are traded for turntables stocked with a collection of records. Each evening, we built a fire in the fireplace and enjoyed the sweets left during turndown service. It quickly became our favorite way to end the day.

Nightly Dinners Done Right

Meals were included daily, and breakfast and lunch featured both made-to-order options and prepared grab-and-go selections that made early excursions easy. I may or may not have developed a habit of grabbing one of their oversized cookies each afternoon.

Dinner was served at Horn & Cantle, the ranch’s Wine Spectator-recognized restaurant housed inside a beautiful log building that somehow feels both elevated and completely unpretentious.

Just off the dining room, the saloon came alive each evening with live music and a roaring fireplace. One evening we enjoyed snacks and cocktails before dinner in the members-only Auric Room. Cell phones were collected at the door, creating a wonderfully relaxed setting where conversation naturally replaced screens. The martinis were excellent.

But if I had to choose one evening that captured the spirit of the ranch, it would be Sunday.

An incredible spread!

The weekly barbecue brings everyone together for smoked meats, classic Western sides, live music, line dancing lessons, and s’mores around the fire pits as the sun begins to set behind the mountains. Our “Uber” for the evening featured Belgian draft horses pulling covered wagons to dinner.

When Don and I got married, my parents took ballroom dancing lessons and continued dancing socially for years afterward. Two new hips and many years later, my dad quietly asked the band to play a song they could dance the rumba to. Watching them celebrate so many years together on the dance floor reminded me exactly why we’d all traveled west in the first place.

I’ll admit I got a little emotional. 🙂

Cowboys & Cowgirls

Another evening was spent at the weekly rodeo held right on the ranch.

Unlike the staged performances some travelers might expect, this felt like a genuine community event. Local wranglers competed in events like barrel racing, ranch roping, and Old West bronc riding. One of the crowd favorites featured local kids scrambling into the arena in pursuit of a flag attached to a calf.

Many of the competitors are working toward professional rodeo careers, which made the competition feel authentic rather than performative.

There was something wonderfully Americana about the entire evening, especially as our country approaches its 250th anniversary. It was one of those experiences that reminded me how travel introduces us to traditions that are simply part of everyday life somewhere else.

One of Lone Mountain Ranch’s most popular weeks each year is Cowgirl Up, a women-only event held every fall featuring sunset trail rides, yoga, fly fishing, rodeo, a Denim & Diamonds celebration in the saloon, winemaker dinners, and plenty of opportunities to meet women who share a love for the outdoors.

I’m already figuring out how to attend in 2027.

A Familiar Brand in an Unexpected Place

My mom and I spent one afternoon at the One&Only Spa, and it was the perfect way to slow down after several active days.

Having previously stayed at One&Only resorts in Los Cabos and Cape Town, I was curious to see how the brand would translate to Moonlight Basin, its first U.S. property.

The same gracious hospitality, beautiful design, and attention to detail carried through every part of the experience, simply interpreted through a mountain landscape instead of an ocean view.

The spa was outstanding. Cozy massage tables layered with oversized furry blankets, thoughtful treatments, and a relaxation lounge featuring oxygen and chlorophyll water left us feeling completely restored before heading back to the ranch.

The Activity I’ll Never Forget

Horseback riding was everyone’s favorite activity of the week.

For me, though, it represented something a little different.

I’ve always had a healthy fear of heights (and falling), and anyone who knows me well knows I’m a bit of a klutz. And so I have always been afraid of horseback riding, plus I had always been told I was severely allergic to horses. Before arriving at Lone Mountain Ranch, I did a little homework after learning horses can sense your emotions. So instead of focusing on everything that could go wrong, I focused on staying calm, learning my horse’s personality, and trusting the experience.

We were able to fit in two separate rides. The first introduced us to ranch riding, taught us that my brother couldn’t keep his horse from stopping for snacks, confirmed my nephew is a natural in the saddle, and revealed that the most appropriately named horse on the ranch belonged to my husband: Blazing Saddles.

The second ride took us deeper into the surrounding landscape. Two hours with my boy Hank, and I fell into an easy rhythm. The wrangler had shared that my boy throws his head while riding and that’s just how he exists. Knowing and accepting this little quirk helped me feel much more at ease. Somewhere along the trail, I stopped thinking about what could go wrong. I trusted that Hank would take care of me, and in return, I tried to reassure him along the way.

It was relaxing, invigorating, and empowering all at once.

Next Week...

In Part II, we’ll make our way south to Jackson, Wyoming, where we’ll explore Grand Teton National Park, float the Snake River, discover one of my favorite mountain towns in America, and share why dressing the part is half the fun.

Have a safe and Happy 4th of July weekend!

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Cartagena is HOT right now, literally and for those in the know.

For many of us, Colombia was our first introduction to adventure travel long before we ever stepped on a plane. We watched Romancing the Stone, dreamed of jungles, treasure maps, and faraway places, and imagined a country that felt mysterious and exotic.

Cartagena is none of those things.

Instead, I found a sophisticated, welcoming city with remarkable food, beautiful design, genuine hospitality, and enough reasons to return that I’m already thinking about a future visit.

I was lucky enough to experience Cartagena alongside dear friends, one of whom grew up there. Seeing any destination through the eyes of someone who knows it intimately is an unmatched experience. The restaurants, traditions, neighborhoods, and stories behind them create a much deeper connection to a place than any guidebook ever could.

Anytime you’re invited to explore someone’s hometown with them, say yes.

The opening of Four Seasons Cartagena this spring has also catapulted the city to the top of many travelers’ lists, and after spending several days there last month, I completely understand why (see my full review of the Four Seasons here).

A vibrant food scene, excellent shopping, island oases, and local leadership that has transformed this historic city into a safe and welcoming destination make it somewhere we already hope to return to.

Admittedly, Cartagena wasn’t at the top of my places-to-visit list. Not because I’d heard anything negative, quite the opposite. I simply assumed I’d experience it someday on a cruise itinerary or as part of a longer South American journey.

What I learned is that Cartagena deserves to be the reason for the trip.

What We Did

We mostly walked. About 10,000 hot steps per day.

The beauty of Cartagena is that much of the historic center is incredibly walkable. Days naturally unfolded between wandering the colorful streets of the Old City, exploring Getsemaní, stopping for cocktails, shopping, and then sitting down for yet another memorable meal.

Getsemaní was one of my favorite discoveries. Once a working-class neighborhood just outside the city walls, it has evolved into one of Cartagena’s most vibrant districts. Street art, music, local fruit vendors, lively plazas, and restaurants spill onto the sidewalks. It’s impossible not to feel the energy.

One morning, our friend introduced us to a variety of local fruits I’d never tried before. It was one of those simple travel moments that sticks with you long after you’ve returned home.

The breakfast at Four Seasons deserves its own mention. It’s one of the most impressive hotel breakfasts I’ve experienced. I never even made it to the custom omelet station because I was too busy working my way through local fruits, Colombian specialties, and fresh juices each morning.

Beyond Cartagena

While Cartagena easily stands on its own for a long weekend, one of the things that makes Colombia so compelling is the opportunity to pair it with entirely different landscapes and experiences.

Few destinations rival Colombia’s geographic diversity. Snow-capped Andean peaks give way to rolling coffee hills, dense Amazon rainforest stretches into untouched wilderness, and both Caribbean and Pacific coastlines offer completely different expressions of tropical beauty. In a single journey, travelers can move from the cosmopolitan energy of Bogotá to the colorful streets of Cartagena, all while experiencing a remarkable range of ecosystems, cultures, and cuisines.

Colombia’s geography makes this surprisingly easy. Situated at the crossroads of North and South America, the country enjoys year-round travel thanks to its equatorial location, while the Andes Mountains create a variety of climates and landscapes within relatively short distances.

If I were returning with more time, I’d pair Cartagena with Colombia’s Coffee Region, where rolling green hills, charming towns, and some of the world’s most celebrated coffee create a completely different experience. Bogotá would also make a fascinating addition for travelers interested in art, history, and a more urban perspective on the country.

That’s perhaps what impressed me most. Cartagena may have been the reason for this trip, but it also left me wanting to see much more of Colombia.

The Best Day of the Trip

When the afternoon heat became too much, we escaped to the islands, which is very much a part of their culture.

And yes, you can rent an entire island.

For just several hundred dollars per person, we spent the day at Isla Amores, a beautiful private island within the Rosario Islands and owned by a gentleman who has four boutique properties in Cartagena (who we had the chance to meet). There were several areas to swim and snorkel and plenty of loungers in the sand. We arrived to mezcal margaritas and settled into a day that felt wonderfully removed from reality.

Lunch included fresh fish, empanadas de carne y queso, shrimp in a light garlic sauce, and the kind of meal that reminds you why seafood tastes better when you’re staring at the ocean.

What surprised me most was that Isla Amores isn’t just a day trip destination. There are cabins available for overnight stays, and after spending the afternoon there, I could easily see adding one or two nights to a future itinerary, and it would be perfect for a bachelorette party, yoga retreat, or friends celebrating a milestone birthday.

Dining & Cocktails

Admittedly, this is the first destination I’ve visited in Central or South America where my stomach never once protested.

And we ate. A lot.

Three full meals a day, which is considerably more than my typical routine.

The menus were filled with fresh seafood, steaks, tropical fruits, and what may be the best coconut rice I’ve ever eaten. Slightly sweet, incredibly flavorful, and somehow the perfect complement to nearly everything on the plate.

The cuisine felt approachable and ingredient-driven. Nothing was overly spiced or overly complicated. Just excellent products prepared thoughtfully.

One ingredient that seemed to appear everywhere was hearts of palm. My favorite preparation combined hearts of palm with mango, pomegranate, arugula, and olive oil. It’s already on my list to recreate at home.

A few standouts:

Alquímico – One of Cartagena’s most celebrated cocktail destinations and a must for anyone interested in the city’s creative bar scene.

Donjuan – Elevated Colombian cuisine that consistently appears on “best of Cartagena” lists for good reason.

Apogeo – A modern tasting menu experience showcasing Colombian ingredients through a contemporary lens.

Cande – Lively, colorful, and deeply rooted in local culture.

La Vitrola – A Cartagena classic with old-world charm, live music, and a menu focused on Caribbean flavors.

The Grand Grill at Four Seasons – Major Food Group’s first venture in Colombia, blending Cartagena’s coastal influences with the group’s signature style.

Shopping

With designers like Silvia Tcherassi and Johanna Ortiz calling Colombia home, it’s no surprise that Cartagena has become a shopping destination in its own right.

The influence of quality fabrics, tailored silhouettes, and feminine design is everywhere.

My favorite discoveries included Malva and Porto de Almas, both showcasing a thoughtful mix of Colombian designers and artisans.

For home goods, I loved browsing Pez en el Agua, where handcrafted pieces are created by indigenous Colombian people paid fair and livable wages. We picked up the cutest napkin rings that will keep memories from the trip alive each time we use them.

A Few Things That Surprised Me

The city felt remarkably clean.

There were very few stray animals.

The women are impeccably dressed.

And despite the age of the historic streets, there was a noticeable sense of pride in maintaining the city.

Most of all, I was struck by the hospitality. Everywhere we went, people seemed genuinely proud of Cartagena and eager to share it.

A Final Thought

Cartagena may have arrived on my radar because of a new Four Seasons, but it’s the people, food, culture, shopping, and history that will bring me back. And unlike Joan Wilder, I didn’t leave Colombia with a treasure map.

I did leave with a longer list of places I’d like to explore next.

Some destinations are wonderful additions to a larger itinerary.

Others deserve to be the reason for the trip.

Cartagena is one of them.

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A peaceful morning walk along Ocean Boulevard

Hi friends,

I don’t know about you, but May absolutely flew by.

Between a trip to Palm Beach, a long-awaited getaway to Cartagena, hosting friends and family, attending a DMB concert, launching the new Tampa Community Hub through Fora, and welcoming new clients, it’s been one of those months where I occasionally had to look at my calendar just to remember what city I was in and what day it was!

There were some exciting milestones mixed in too. I reached Pro status through Fora for the second year in a row, and three months faster than last year. More importantly, it reflects something I’ve been working hard on behind the scenes: building relationships with hotel partners, expanding the types of trips I plan, and continuing to learn so I can better serve my clients.

The best part? Many of the destinations I’m helping clients plan right now are also inspiring my own future travels. Scotland, the French Riviera, Sardinia, and a few others are quickly moving up my personal wish list.

Sometimes the best research trips are the ones where you arrive with no expectations and leave wondering why you hadn’t visited sooner.

That was Palm Beach.

I recently spent less than 48 hours there and somehow managed to pack in hotel tours, meals, shopping, and enough walking to justify every bite. Palm Beach has long been associated with old money, socialites, and Worth Avenue, but what I found was a destination that’s surprisingly approachable. There’s history, beautiful architecture, excellent dining, great shopping, and some truly exceptional hotels.

If you’re looking for a long weekend that feels equal parts glamorous and relaxed, Palm Beach deserves a spot on your radar.

Here’s where I’d stay, dine, shop, and wander.

Xx,
Christy

Why Palm Beach?

Palm Beach has a way of feeling both timeless and relevant.

The destination is known for its historic hotels, palm-lined streets, iconic shopping, and social scene, but beneath the glamour is a surprisingly walkable and approachable town.

It’s an ideal destination for couples, girlfriends’ getaways, celebrations, and anyone who appreciates great hospitality, thoughtful design, and being able to walk from the beach to lunch to shopping without ever getting in a car. Whether you’re looking for a full-service beachfront resort or a boutique hideaway near Worth Avenue, Palm Beach offers a style of luxury that feels distinctly Floridian.

Where to Stay

After my site visit of The Breakers in their stunning lobby, featuring fresh florals

The Breakers Palm Beach

Best for: you want a large-scale resort done right

Old Florida glamour at its best, with expansive grounds, multiple pools, a beautifully executed spa, championship golf, and a beach club with no shortage of places to settle in for the day. Despite its size, the service remains polished and attentive, which is what continues to set it apart.

Read my full write-up:
https://www.foratravel.com/trip-reports/CZ4ELJ/the-breakers-palm-beach-classic-florida-luxury-that-still-delivers-christy-agee

The Vineta Hotel

Best for: a design lover’s version of Palm Beach luxury

Picture a highly detailed boutique experience where Oetker Collection’s attention to detail shows up everywhere, from thoughtfully designed seating areas to in-room fitness kits and beautifully appointed bathrooms. With a more intimate scale and polished residential feel, it delivers a quieter, more refined alternative to the larger Palm Beach resorts.

The Colony Hotel Palm Beach

Pink exterior and welcome cart at The Colony

Best for: you want to be in the center of the social scene

Iconic pink interiors, poolside lunches that turn into afternoon cocktails, and one of the best locations in Palm Beach just steps from Worth Avenue. The rooms tend to run smaller, but that’s part of the charm. The Colony is less about resort amenities and more about atmosphere, personality, and feeling plugged into the heart of Palm Beach.

The Brazilian Court Hotel

Best for: you want a peaceful respite from the Palm Beach scene

Quiet courtyards, classically designed rooms layered in mahogany and soft neutrals, and one of the island’s strongest dining destinations at Café Boulud. While some accommodations show their age a bit compared to newer luxury offerings on the island, the charm, location, and overall sense of place remain the real draw. It feels discreet, residential, and removed from the energy of Worth Avenue while still being close to everything.

White Elephant Palm Beach*

Best for: understated luxury with a residential feel

This is a quieter, more contemporary interpretation of Palm Beach luxury, with brighter interiors, a softer coastal aesthetic, and a less formal atmosphere than many of the island’s legacy properties. White Elephant feels relaxed, design-forward, and highly polished without ever feeling showy.

Four Seasons Resort Palm Beach*

Best for: beachfront luxury with consistently exceptional service

A calm oceanfront retreat where the emphasis is less on the Palm Beach social scene and more on seamless service, wellness, and beach time. Unlike The Breakers’ grand scale, the Four Seasons offers a quieter and more intimate resort experience.

*I did not personally visit these properties during this trip but heard consistently positive feedback from both travelers and industry colleagues.

Where to Dine

The perfect lunch overlooking a courtyard at Cafe Boulud

Buccan

The reservation everyone wants. Chef Clay Conley’s menu blends creative small plates with a lively atmosphere, making it one of the most consistently recommended restaurants on the island. James Beard recognized and a menu with enough variety for everyone. My hubs was delayed getting in and so I went to snag a bar seat and enjoyed dinner within about 30 minutes of arrival.

Le Bilboquet

The market carries classic French pastries, giftable items like Moutarde de Meaux Pommery mustard, chocolates plus a full service restaurant next door, which is Palm Beach’s answer to the see-and-be-seen lunch. The French-inspired menu is excellent, but the real draw is lingering over a glass of rosé while taking in the scene. If you’re looking for a quintessential Palm Beach afternoon, this is it.

Café Boulud

One of Palm Beach’s best dining experiences, tucked inside the Brazilian Court. Refined French cuisine meets Palm Beach sophistication in a setting that feels elegant without being stuffy. I had the best gazpacho during a lunch visit.

Polo Bar

Classic Palm Beach. Think people-watching, cocktails, and a scene that feels distinctly tied to the social fabric of the island. Excellent steaks, pastas, seafood and plenty of options for vegetarians.

Don’t Miss

One of my favorite discoveries was simply wandering Palm Beach on foot.

Tucked between Worth Avenue and the surrounding streets are a series of hidden pedestrian passages known as the vias. Lined with bougainvillea, courtyards, fountains, and charming architecture, they felt more like something I’d stumble upon in Europe than in South Florida. I found myself repeatedly turning corners just to see what was around the next bend.

Serious orchid envy

With less than 48 hours in town, I didn’t have time to do everything on my list. Next visit, I’m looking forward to exploring the Society of the Four Arts gardens and spending time at the Flagler Museum to better understand the history that shaped Palm Beach into what it is today.

Where to Shop

The beautiful Johanna Ortiz boutique inside The Brazilian Court

Johanna Ortiz

My personal favorite. The Palm Beach boutique inside The Brazilian Court carries the Colombian designer’s signature resort wear, feminine silhouettes, and effortlessly chic pieces that feel perfectly suited to the destination. Don’t miss her stunning straw bags, which I feel like I’m always hunting for the perfect version.

Marina St. Barth

Colorful, breezy, and vacation-ready. A great stop for discovering European and island-inspired fashion brands. The sales team is top notch and endlessly helpful. Grab a drink beforehand in Bici to make shopping extra fun.

Poupette St Barth

If Palm Beach had an unofficial uniform, it might include something from Poupette St Barth. Easy dresses, vibrant prints, and pieces that transition seamlessly from beach to dinner. Feminine designs fit for real figures.

Stephen Mooney Interiors

One of my favorite discoveries from the trip. Whether you’re actively decorating or simply appreciate beautiful spaces, it’s worth stepping inside for inspiration alone. We found a spoon warmer in the shape of a conch shell and door stop with elephant and palm tree.

Finding the perfect dress for a summer party at Marina St. Barth’s

A Final Thought

Palm Beach surprised me.

I expected beautiful hotels and good shopping. What I didn’t expect was how much personality each property had, how walkable the town felt, and how easy it was to fill two days without ever feeling rushed.

It’s a destination that works whether you’re looking for a girls’ getaway, a romantic weekend, or simply a change of scenery without a long-haul flight.

We already have an anniversary trip to The Breakers on the calendar, which means I’ll happily continue my research and report back.

One of the things I love most about travel planning is that there is rarely a single “best” answer. The best hotel, destination, itinerary, or cruise line is usually the one that best matches your travel style, interests, and priorities.

The Breakers isn’t better than The Vineta. The Brazilian Court isn’t better than White Elephant. They’re simply different experiences designed for different travelers.

My job isn’t to tell you where to go. It’s to help you find the place that’s right for you.

And if you’re wondering which Palm Beach hotel is right for your travel style, you know where to find me.

Work with me

My husband Don with his father at Pebble Beach.

Growing up, travel was always something we valued as a family.

Not necessarily because everything was luxurious or elaborate, but because experiences together became the stories we continued telling years later, and still do to this day. We were lucky to experience Hawaii, Disney, and even Branson, Missouri, complete with an unforgettable road trip home. Word to the wise: Don’t pair red Gatorade with soft serve ice cream.

Several years ago, my husband started taking his dad on an annual golf trip. They started with Pebble Beach, because why not start with the best, and most recently visited Streamsong Golf Resort, about 90 minutes from Tampa. After each trip, my husband even created memory books through Shutterfly as a keepsake and gift for his dad.

There’s something especially meaningful about trips between fathers and sons, fathers and daughters, or multi-generational family travel in general. The shared experiences, inside jokes, and unexpected moments have a way of becoming part of your family history.

And while Father’s Day gifts are wonderful, I’ve increasingly come to believe that experiences are what stay with us the longest.

So in honor of Father’s Day, I wanted to share a few trip ideas inspired by the kinds of experiences the men in my life have loved most, from bucket-list golf and rugged outdoor adventures to history-focused itineraries and event-driven travel.

For the Golf Lover

Golf trips have long been a tradition in Don’s family, and some of the most memorable journeys have revolved around iconic courses and time spent together on them.

St. Andrews & Scotland

For the golfer who appreciates history as much as the game itself, there’s nothing quite like Scotland. Playing St. Andrews is a bucket-list experience, but the real magic often comes from the rhythm of the trip itself: Dramatic scenery, whisky tastings, castle hotels, and evenings spent recounting the day over dinner.

Pebble Beach, California

Pebble Beach is iconic, and it’s easy to understand why. The combination of oceanfront scenery, legendary golf, and classic hospitality makes it feel special from the moment you arrive. Pair it with a drive along the Pacific Coast Highway (see this great piece in NYT Travel Dispatch) or extend the trip into California wine country.

PGA National, Florida

For something easier to access domestically, PGA National offers a relaxed, golf-focused getaway with multiple award-winning courses, warm weather, and resort amenities that make it appealing even for non-golfers.

Golf by Superyacht

One of the more interesting concepts I’ve come across recently is the Ritz-Carlton Yacht Collection’s golf-focused voyages, pairing luxury cruising with access to renowned courses and destinations throughout the journey.

For the Outdoorsman

Some trips are less about sightseeing and more about being immersed in nature.

Boundary Waters, Minnesota & Canada

My dad first went to Boundary Waters with his own father and later carried on the tradition by taking my brother. Remote lakes, early mornings, campfires, and completely unplugging from everyday life are what make trips like these so memorable.

Fly Fishing Retreats

Whether it’s Montana, Wyoming, or Patagonia, fly fishing trips offer a slower pace and a deep appreciation for landscape and craftsmanship. Even non-fishermen often fall in love with the rhythm of these trips.

Dude Ranches

For fathers traveling with younger kids or teens, luxury dude ranches can be incredibly fun, blending horseback riding, hiking, fishing, and wide-open landscapes with surprisingly elevated accommodations and food.

Iceland

For adventurous dads, Iceland offers a little bit of everything: rugged scenery, waterfalls, glacier hikes, geothermal spas, wildlife excursions, and dramatic drives that feel almost otherworldly.

For the History Buff

For some travelers, a destination becomes most meaningful when you understand the stories behind it.

Normandy, France

A deeply moving experience, particularly for multi-generational trips. Visiting the D-Day beaches, cemeteries, and museums adds an emotional depth that stays with you long after returning home.

Munich & Bavaria

If timing aligns with Oktoberfest, it can become a surprisingly great jumping-off point for a broader historical itinerary through Bavaria, with castles, beer halls, and WWII history layered throughout the region.

Washington, D.C.

Sometimes we overlook destinations closer to home. D.C. offers incredible museums, monuments, and American history while also being a very approachable long weekend destination for fathers and kids of all ages.

Around an Event

Some of the best itineraries are built around a singular event or passion.

Watches & Wonders, Geneva

For watch enthusiasts, Watches & Wonders has become one of the premier global showcases for luxury timepieces and craftsmanship. Pairing Geneva with the Alps, lake towns, or even northern Italy creates a highly memorable itinerary.

Oktoberfest, Germany

Yes, it’s lively and touristy, but it’s also one of the world’s great cultural festivals. The key is building a broader itinerary around it so the trip becomes about more than just the event itself.

Mexico City & The World Cup

With the World Cup just around the corner, Mexico City is shaping up to be one of the most exciting places to experience the energy of the tournament. Beyond the matches themselves, the city offers incredible food tours, lucha libre matches, nearby pyramids, and some of the best restaurants in the world, making it a destination that blends culture, history, and excitement effortlessly.

The best trips often aren’t the most elaborate or expensive ones. They’re the ones that surprise you, create new traditions, and become stories your family continues telling years later.

At the end of the day, you probably already know what your dad would love most. And if you don’t, ask him. He’ll be thrilled at the thought of going somewhere with you.

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As a former project management professional, I am a chronic overthinker, constantly calculating scenarios like a choose-your-own-adventure game in my mind. I like to be prepared before problems arise. I can step in, pivot quickly, and know what to do when things don’t go according to plan.

The reality, of course, is that life throws curveballs, and you can never plan for everything.

You’re preparing for the trip you’ve spent the last year dreaming about. You’ve carefully chosen the hotels, booked the flights and tours, set aside the funds, and then suddenly life throws you a twist that makes taking that trip impossible. It’s an unfortunate part of our human reality, but it’s also something we can actually prepare for.

For years, I wasn’t a big believer in travel insurance. I planned most of our trips myself, reviewed the cancellation policies, and figured if we lost a hotel deposit, no big deal. At the time, we weren’t staying anywhere where the loss of a night or two would significantly impact our finances. I was willing to take the risk on accommodations without fully considering what could happen if we got sick abroad.

Then we started traveling to more remote places, and I realized how vulnerable we actually were.

I learned that our domestic health insurance wouldn’t necessarily cover us overseas if we needed treatment, hospitalization, or, worst-case scenario, emergency medical evacuation. At that point, we started carrying supplemental international medical coverage through BCBS Global Core, specifically for healthcare abroad.

I look back now at our safari to Africa and realize we could have faced staggering medical evacuation costs had something serious happened. I’m not trying to scare anyone, but I do think it’s important to understand the realities of the risks we take when we travel.

And after Covid, the rules of the game changed significantly.

Hotel cancellation policies became much stricter, particularly at luxury properties. Credits and rebooking flexibility narrowed. Credit card protections, while still valuable, often provide limited assistance unless the reason for cancellation falls within very specific guidelines.

I recently heard a story from a friend whose partner left her bag in an Uber after returning home from an international trip. Inside were family passports, jewelry, cash, and several sentimental items. Her travel insurance provider stepped in immediately, helping investigate the loss and reimburse covered items according to the terms of her policy.

That story stuck with me because it highlighted something important: travel insurance isn’t only about catastrophic emergencies.

This is why I now strongly encourage my clients to explore comprehensive travel insurance coverage based on the nature of their trip and personal risk tolerance. Depending on the policy, travel insurance may:

• Protect your investment in accommodations, tours, flights, and prepaid experiences

• Provide reimbursement for lost, delayed, or stolen belongings

• Help cover emergency medical treatment abroad

• Assist with medical transportation or evacuation

• Offer 24/7 support while traveling

Because while no one likes thinking about what could go wrong, having a plan in place allows you to focus much more fully on what hopefully goes right.

Cancel For Any Reason Isn’t Always “For Any Reason”

One of the most misunderstood components of travel insurance is Cancel For Any Reason coverage, often referred to as CFAR. People hear the name and assume they can cancel at any point for any reason and receive a full refund. Unfortunately, that’s not usually how it works.

CFAR policies are typically an add-on to a comprehensive policy, cost more, and often reimburse only 50-75% of your prepaid, nonrefundable trip expenses. Timing also matters. Many policies require you to purchase coverage within a relatively short window after your first trip deposit, often within 14-21 days.

That said, there are situations where it can absolutely make sense, especially for larger trips with significant prepaid costs or for travelers who simply want the peace of mind that comes with additional flexibility. Some CFAR policies offer coverage for pre-existing conditions if the standard policy does not. Or if you are uneasy when global events bring added stress that is no fun while you’re traveling.

The important takeaway is this: not all travel insurance policies are created equal, and this is where reading the details, or working with someone who understands the nuances, really matters.

Is Your Credit Card Enough?

One of the most common assumptions I hear is, “I booked the trip on my credit card, so I’m covered.”

And while many premium credit cards do offer some level of travel protection, the coverage is often much more limited than people realize.

Some cards may help with delayed baggage, trip interruptions, or rental car coverage, but many do little when it comes to overseas medical treatment or emergency medical evacuation, which can become extraordinarily expensive very quickly.

After Covid, cancellation policies have also become far stricter, particularly at luxury hotels and resorts. If you need to cancel within the penalty window, your credit card benefits alone may not offer meaningful protection unless the reason falls within very specific guidelines.

I still absolutely leverage the benefits of my credit cards while traveling, but I no longer view them as a replacement for comprehensive travel insurance, especially on more expensive or remote trips.

Trips I’d Rarely Take Without Insurance

There are certain trips where I personally wouldn’t feel comfortable traveling without comprehensive coverage in place.

Safari is high on that list. Once you’re deep in a reserve or moving between bush planes and remote lodges, the logistics of receiving emergency medical care become very different from being in a major city.

The same applies to expedition cruises, Antarctica, ski trips, or multi-stop itineraries where weather delays and missed connections can create a domino effect throughout the rest of the journey.

Even destinations that feel relatively straightforward, like Europe, can become complicated quickly if you need hospitalization abroad or suddenly have to cancel a significant prepaid itinerary.

And honestly, sometimes it’s not even the catastrophic scenarios that matter most. It’s the smaller but still stressful moments: delayed luggage, missed flights, lost passports, or needing assistance navigating an unfamiliar system in the middle of a difficult situation.

Travel insurance can’t prevent things from going wrong. But it can provide support, protection, and peace of mind when they do.

When an Annual Policy Might Make Sense

If you travel frequently, an annual travel insurance policy can sometimes make more sense than purchasing individual coverage for every trip.

These policies are designed for travelers who take multiple trips throughout the year and can provide ongoing coverage for things like emergency medical care, evacuation, trip delays, baggage protection, and certain interruption benefits.

This can be especially appealing for travelers who:

• Take several international trips annually

• Book frequent long weekends or cruises

• Travel for both business and leisure

• Want the simplicity of continuous coverage

That said, annual policies aren’t always a perfect substitute for standalone trip insurance. Some have lower coverage limits for trip cancellation or interruption, and many travelers still choose to supplement major trips, especially safaris, expedition cruises, or high-dollar itineraries, with additional coverage tailored specifically to that journey.

Like most things with insurance, the best option depends on your travel habits, risk tolerance, and the complexity of the trips you’re taking. But if you find yourself traveling often, it’s absolutely worth exploring whether an annual policy could provide both convenience and peace of mind.

A Final Thought

Good travel planning isn’t about expecting something to go wrong. It’s about protecting the investment, time, and experiences that matter most to you.

Travel insurance may not be the most exciting part of planning a trip, but after years of travel, and seeing firsthand how quickly circumstances can change, it’s become one of the most important.

As always, if you ever want help understanding what level of coverage may make sense for a specific trip, I’m always happy to talk it through from my perspective as a traveler and advisor.

Disclaimer: I am not a licensed insurance agent, and the information shared in this newsletter is based solely on my personal experiences, research, and perspective as a traveler and travel advisor. Coverage, exclusions, and policy terms vary significantly by provider and policy. Travelers should always review policy details carefully and consult directly with a licensed insurance professional or provider to determine what coverage is appropriate for their specific needs and circumstances.

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Every time I book a trip, it opens the door to somewhere new and unexpected. The world is vast, and it’s not always easy to prioritize where to go and when, especially when work, pets, family, finances, and the general pace of life don’t always allow for extended time away.

Scotland has long been on my list, but it wasn’t until some clients recently reached out to plan their first overseas trip in five years that I really started to dig in. What had been a “someday” destination quickly began moving closer and closer to the top for so many reasons.

As I started building out a few different itinerary options, what struck me most was the sheer range of experiences you can layer into a relatively compact trip. There’s the obvious draw of bucket-list golf, but also horseback riding, spa experiences, romantic castle stays, and scenic drives through the countryside where you can stop for a picnic next to a waterfall.

Add in whisky tastings across the Highlands or Speyside, the history and energy of Edinburgh, and even a few pop culture moments like the Glenfinnan Viaduct or Outlander filming locations, and you start to see just how dynamic a trip like this can be.

And then, of course, I started thinking about the food.

Scotland isn’t necessarily the first place that comes to mind as a food destination, but the more I’ve researched, the more I’ve realized that’s part of what makes it so interesting. There’s a deep appreciation for seafood and local meats, often prepared simply, with a strong farm-to-table ethos that has been part of the culture for generations.

It reminded me of something I think about often when traveling. The best meals aren’t always the most elaborate. They’re the ones that feel connected to where you are. I noticed this again just last week during a trip to Gasparilla Inn in Boca Grande. The restaurants that stood out weren’t trying to be anything they weren’t. They leaned into local ingredients, prepared thoughtfully and simply.

When expectations align with place, the experience becomes so much more meaningful. You don’t go into a seaside fish shack expecting something it’s not. Instead, you look for what the destination does best, and that’s where the magic tends to happen.

As Anthony Bourdain often said, seek out what’s local, what’s authentic, and what tells the story of a place. Scotland, it seems, does exactly that.

The same goes for what’s in your glass.

As much as I love a great glass of wine with dinner, not every destination is defined by wine. Some places are better understood through their local beverages, and in Scotland, that story is told through whisky. There’s a sense of place, history, and craft behind it that makes the experience feel just as intentional.

The Hotel (or Castle) is the Experience

Scotland is one of those destinations where the hotel is the experience. The country is moody in the best way, with dramatic landscapes, rugged coastlines, waterfalls, rolling hills dotted with Highland cows, and centuries-old castles with stories we can’t even imagine.

And your hotel becomes part of that story.

Mornings begin slowly, with a proper breakfast before stepping out into the surrounding landscape, perhaps for a hike just beyond the property or a scenic drive with no real agenda. You might stop for a picnic beside a waterfall or take part in something quintessentially Scottish like falconry, leaning into the traditions of the land.

By late afternoon, the pace naturally shifts. You return, settle in, and let the day wind down with tea or a cocktail by the fire before dinner.

It’s this rhythm that defines a trip to Scotland. The setting, the pace, and the sense of place all come together, making the hotel not just where you stay, but an essential part of how you experience the country.

With that in mind, as I’ve been building out these itineraries, I found myself gravitating toward a handful of properties that really embody this feeling, places where you could just as easily spend the day on property as you could exploring beyond it.

Gleneagles: Easing Into the Trip

Gleneagles, one of Scotland’s most iconic estate hotels, offering championship golf, horseback riding, and a beautiful countryside setting.

If I were planning this trip for myself, I wouldn’t start in Edinburgh.

After a long international flight, the idea of stepping straight into a city feels like too much too soon. Instead, I like heading directly into the countryside, where you can ease into being away.

That’s where Gleneagles comes in.

Set just over an hour from Edinburgh, it’s the kind of place that immediately shifts your mindset. You arrive, settle in, and explore the surroundings.

Days can be as active or relaxed as you want. There’s golf, horseback riding, falconry, and a full spa, but just as easily, you can spend your time walking the grounds, enjoying meals in their stunning dining areas, or simply enjoying the scenery.

With multiple dining options on property, it’s easy to anchor your days around food without ever feeling repetitive. A more formal dinner one night, something lighter the next, perhaps afternoon tea in between.

More than anything, Gleneagles allows you to arrive, exhale, and transition before continuing on.

From there, the shift into the Highlands feels natural.

The Highlands: Where the Trip Slows Down

This is where Scotland leans fully into its moodiness.

The landscapes become more dramatic and the roads quieter. It’s less about checking off sights and more about experiencing the setting as you move through it.

As I’ve been building these itineraries, one of the most important decisions has been how far north to go, or whether to focus more on the western Highlands. Each offers a slightly different experience, and that choice can really shape the overall feel of the trip.

For a first visit, I tend to focus on the western Highlands, which pair naturally with the Isle of Skye and offer some of the most iconic scenery in the country. This is where you’ll find places like Glencoe, with its dramatic valleys and winding roads, and Fort William at the base of Ben Nevis. It’s also where experiences like the Glenfinnan Viaduct (for Harry Potter fans) and ferry crossings to Skye fit seamlessly into the journey. The landscape feels immediate and cinematic, without requiring overly long travel days.

Heading further into the northern Highlands, particularly around Inverness and into Speyside, the atmosphere shifts. The terrain opens up, the roads stretch longer, and the sense of remoteness deepens. This region is especially compelling for those interested in whisky, with some of Scotland’s most renowned distilleries, including Macallan, Glenfiddich, and Dalmore, all within reach. It’s also where you’ll find historic sites like Culloden Battlefield, offering a powerful and grounding look into Scotland’s past.

Both regions are incredibly rewarding, but they lend themselves to slightly different styles of travel. The west feels more visually dramatic and accessible, while the north offers a deeper dive into history and whisky, often best suited for those with more time or a specific interest in exploring further.

Regardless of the route, days are often shaped by the drive itself. Winding through valleys, stopping when something catches your eye, whether that’s a scenic overlook, a quiet stretch of water, or simply a moment that feels worth pausing for.

Where you stay becomes even more important here.

Inverlochy Castle offers a classic Highland experience, intimate and refined, while Glencoe House provides a more private, residential feel. And for something completely unique, The Fife Arms in Braemar brings a creative, character-driven energy that feels deeply connected to its surroundings.

Meals become part of the ambling routine, often enjoyed at your hotel after a day outdoors, with menus focused on local seafood, game, and seasonal ingredients.

This part of the journey isn’t about filling every moment. It’s about creating space to take it all in, the landscape, the history, and the quieter moments in between that tend to stay with you the longest.

After several days of open landscapes and a slower pace, returning to a city brings a different kind of energy.

Edinburgh: Ending on Energy

By the time you arrive in Edinburgh, you’re settled into the rhythm of Scotland, which makes it much easier to fully enjoy the energy of the city.

Days might include exploring Old Town, visiting Edinburgh Castle, or wandering into neighborhoods like Stockbridge or New Town, where it feels more local.

Where you stay sets the tone for your final days.

The Balmoral is a classic choice at the edge of Old Town, offering a polished, full-service experience with an excellent restaurant and whisky bar.

For something more intimate, Prestonfield House feels richly atmospheric, with a strong sense of character and a dining experience worth returning for.

If you prefer something more design-forward, Gleneagles Townhouse brings a modern, social energy with beautifully designed spaces and a lively bar scene.

And for a more boutique stay, 100 Princes Street offers a refined, residential feel overlooking the castle, with thoughtful design.

This is where I’d lean into dining a bit more, anchoring each day with a reservation or two and allowing the rest to unfold naturally.

A curated whisky tasting or guided experience adds context without overwhelming the schedule.

It’s a fitting close to the trip. A bit more energy, a bit more variety, and a chance to reflect on everything you’ve experienced.

A Final Thought

What I’m really designing here isn’t just a route through Scotland, but a slower-paced experience.

One that balances movement with stillness, exploration with time at the table, and structure with space to discover something unexpected.

Because in the end, those are the trips that stay with you. Not the ones where you saw everything, but the ones where you felt connected to where you were.

If Scotland has been on your list, or is starting to move its way there, I’d love to help you shape a version of this trip that feels just right for you.

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In NYC at the theater, and in Paris with my Mom ♥️

With Mother’s Day just one month away, now is the perfect time to start thinking about a gift for the mom in your life. I don’t need to list everything that moms do or have done. That alone could fill an entire newsletter. But as I’ve been thinking about ways to honor and appreciate them, I keep coming back to some of the greatest gifts my own mom has given me through our travels together.

I recognize how fortunate I am to have a mom that is able to travel, and that we love to do so together. I know how hard this time of year can be for so many who’ve lost their moms or are no longer able to enjoy moments I’m about to share. Many of these destinations and special itineraries can also be shared with sisters, aunts, nieces or other ladies in your lives, so hopefully it’s the inspiration you need to find other ways to honor the uniqueness of maternal love.

Maybe your daughter just graduated high school or college, or there’s a milestone birthday on the horizon. Perhaps your own mom deserves a trip where she doesn’t have to plan a thing (please don’t book an Airbnb, that is not a vacation for a mom— she deserves to be waited on). Regardless of the reason, there’s no better gift than creating core memories with the woman who helped shape who you are, through all the joys, tears, frustrations, and victories along the way.

My mom and I once planned a classic girls’ getaway to Paris, where we spent eight days seeing the major sites, wandering through neighborhoods, and discovering cafés and shops we still talk about today. It’s where we learned the art of French cooking, visiting a market in the morning and spending the day in a Parisian’s kitchen, cooking up the best pintade (we use chicken in the states) with a celery root puree.

We got lost in a city together for the first time, complained about bad footwear (mine was truly the worst), laughed through countless inside jokes, and kept a journal of our favorite moments from each day. I still treasure that trip nearly twenty years later.

My mom looking at Napoleon’s jacket, they seem similar in size!

We’ve also taken several trips to New York City, another perfect destination for this kind of travel. Broadway shows, lunches that feel just as intentional as dinner, incredible museums, long walks through Central Park, and the hunt for the perfect boutique hotel. Now that I’m a travel advisor, she’s officially my go-to plus one for any last-minute opportunities, and I can’t wait for the next one to pop up soon.

While those classic destinations will always hold a special place, there are so many other ways to design a meaningful mother-daughter trip. Here are a few ideas, shaped around how you might want the trip to feel.

The Elevated Classic: For duos who want culture and charm with a familiar, easy rhythm

• Lyon, France
  A more intimate alternative to Paris, with incredible food culture, walkable neighborhoods, and a relaxed pace. Spend mornings at Les Halles de Lyon Paul Bocuse, wander through Vieux Lyon, and settle into long bouchon lunches that stretch into the afternoon.

• Montreal, Canada
  European in feel but effortlessly accessible, with a vibrant dining scene and charming neighborhoods. Explore Old Montreal, stop into Jean-Talon Market, and build your days around coffee, shopping, and great meals. Pair with an extension in Quebec City for storybook charm.

The Food & Wine Escape: Where connection happens naturally around the table

• Tuscany, Italy
  Days are best spent visiting small wineries, taking a cooking class in a countryside villa, and lingering over outdoor lunches with vineyard views.

• Santa Barbara, California
  A perfect blend of beach, wine, and walkability. Spend time along the coast, then head to the Funk Zone for an easy afternoon of tasting rooms, restaurants, and small shops. If you’re up for exploring, nearby Los Olivos, Solvang and Santa Ynez offer charming wine country escapes, while Montecito adds a more polished, ultra-luxe touch. It’s a destination that can flex easily, making it ideal for a short but memorable trip together.

The Effortless Luxury: When you want everything handled so you can focus on time together

• Explora Journeys
  A refined take on cruising. Unpack once, wake up somewhere new, and choose between exploring ports or enjoying a slow morning onboard. Many options for reduced or zero single supplements so you can enjoy your own space.

• Rosewood Mayakoba, Riveria Maya
  A lush beachfront retreat where everything is thoughtfully designed. Spend your days biking through the property, enjoying the spa, or booking a private boat through the mangroves before settling in for dinner.

The Cultural Deep Dive: For the curious pair who want to learn, explore, and be inspired

• Florence, Italy
  Art, history, and walkability at the perfect scale. Visit the Uffizi, wander across the Ponte Vecchio, and take a break with aperitivo in a quiet piazza.

• Amsterdam, Netherlands
  Compact and culture-rich. Spend time in the Rijksmuseum or Van Gogh Museum, explore the canals by boat, and enjoy a surprisingly strong dining scene.

• Mexico City, Mexico
  Vibrant and endlessly interesting. Book a food tour through local markets, visit the Frida Kahlo Museum, and balance casual taco stops with standout dinners. Be sure to be in town on a Friday to experience Contramar restaurant, a lively lunch in the beautiful Roma Norte neighborhood.

The Reset Trip: When slowing down is the point

• Longboat Key, FL
  An effortless Gulf Coast escape where you can truly choose your own pace. Stay at the St. Regis Longboat Key for a polished, fly-and-flop experience with a beautiful beach and standout spa, or venture into nearby Sarasota for a change of scenery. Spend an afternoon at The Ringling Museum, browse the shops at St. Armands Circle, or plan a leisurely lunch before heading back for sunset on the water. Also works well for a quick getaway.

• The Ranch, Hudson Valley
  A more structured wellness experience focused on movement, nutrition, and true reset. Ideal if you want to return home feeling completely recharged.

• St. Barth’s
  Beach days, long lunches, and dinners that turn into the highlight of the day. Spend time hopping between beach clubs and exploring Gustavia, with some of the best boutique shopping in the Caribbean.

The Adventure Lover: For duos who want to experience something new, active, or a little outside their comfort zone

• Peru (Sacred Valley + Machu Picchu)
  A truly memorable journey that blends culture, history, and a sense of adventure. Spend time exploring the Sacred Valley, visiting local markets, and taking in the incredible landscapes before making your way to Machu Picchu. It’s the kind of trip that feels both meaningful and energizing, with shared experiences you’ll talk about for years.

• African Safari
  There’s something incredibly special about experiencing a safari together. Early morning game drives, seeing all the mamas and their babies, and sunsets overlooking the savannah recounting the day create an unforgettable experience. I always recommend a smaller game reserve for first timers, but there are plenty of options across South Africa, plus wine country afterwards.

At the end of the day, it’s not really about where you go. It’s about creating the time and space to be together in a way that everyday life doesn’t always allow. The right trip doesn’t need to be complicated; it just needs to be thoughtfully designed around how you want to spend that time together.

However you choose to design it, a mother/daughter trip is one of the most meaningful investments you can make, and one that will stay with you long after you’ve returned home. This is one of my favorite trips to plan and I’d be happy to help craft these memories with you. Just reach out below!

Get in Touch

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I’m so excited about this week’s newsletter. It’s a collaboration that’s been in the works for a while now, with an American living in Bologna, Italy.

I first came across ’s Substack while researching a trip for a client. I’ll share more on that below. I was immediately drawn to her writing. It felt authentic, grounded, and full of the kind of local insight that makes a place come alive. And Bologna is exactly that kind of place. It’s not always at the top of Italy travelers’ lists, but it absolutely should be.

I visited Bologna in 2019 as part of what I still consider one of my favorite trips, a three-week loop through northern Italy. We started and ended in Venice, which, by the way, is one of my favorite ways to experience the country. Italy’s train system makes it incredibly easy to move from city to city without ever feeling rushed.

We made our way through Milan, Turin, Piedmont wine country, attended Truffle Fest in Alba, then on to Florence, Bologna, Modena, and back to Venice. Somewhere along the way, I completely fell in love with Bologna.

There’s something about the city. The miles of porticos, now UNESCO-protected, the energy of a historic university town, and an underlying warmth that you feel almost immediately.

And then, of course, there’s the food.

Truly some of the best I’ve ever had, from casual, deeply local spots like Drogheria della Rosa, where there’s no menu and you’re simply told what’s being made that day, to unforgettable fine dining at Osteria Francescana, where I’ll never forget a Parmigiano Reggiano course with the cheese prepared five different ways.

Over the years, Bologna has become one of my most recommended destinations. It’s approachable, incredibly well connected, and offers a more intimate, authentic lens into Italian culture.

And that’s really what this week is about.

This newsletter is a blend of perspectives. Autumn’s life in Bologna, my own experiences, and places my clients recently loved on their trip earlier this year. We’re bringing it to life through food, too.

I’ll be recreating two of Autumn’s favorite local recipes, starting with Friggione, a slow-cooked onion dish that’s both sweet and savory. And then one of the most delicious and simple pasta recipes using Gramigne, a regional shape, with sausage, tomato sauce, cream, and Parmigiano Reggiano.

Buon Appetito!

Read more

Our selfie after mucho cava

Barcelona and the surrounding area is another fantastic option for a “long-ish” weekend away. We first traveled here in the fall of 2021 with dear friends who were celebrating their anniversary (and me, another birthday), and spent a truly unforgettable day in Penedès with a spectacular producer and now friend, José María Ferrer Noguer of the Freixenet family.

We toured the vineyards, winery, and his home, learning about their winemaking techniques and tasting both cava and still wines, all beautifully paired by his wife Susana. The day ended with a long, leisurely lunch of paella and (far too much) cava. It was one of those perfect travel days you wish you could bottle up! A true celebration of place, people, and new friendships.

While JM has since relocated to Mallorca (future trip!), there are still many exceptional producers in Penedès that can make your visit just as memorable.

In the vineyards at Can Sala.

Cava dates back to the 1870s, when Josep Raventós began producing it as both a response to the success of Champagne and as a way to adapt to the phylloxera crisis that devastated vineyards across Europe.

It’s made using three indigenous grapes (Macabeo, Xarel-lo, and Parellada) and follows the traditional method, meaning a secondary fermentation occurs in the bottle, just like Champagne.

When selecting bottles, look for Brut Nature, which indicates no added sugar (dosage), resulting in a drier, more precise expression of the wine.

There are a few different ways to experience Penedès:

• Stay in Barcelona for energy, culture, and nightlife

• Base yourself in coastal Sitges for a relaxed, seaside feel

• Or head into Vilafranca del Penedès for a more immersive wine country experience

Where to Stay

View from the beautiful rooftop at The Monument

The Monument Hotel — Barcelona
Perfectly located just steps from Passeig de Gràcia, The Monument places you in the heart of Barcelona’s most elegant neighborhood, surrounded by Gaudí architecture, luxury boutiques, and some of the city’s best dining. The property blends classic architecture with a polished, contemporary feel, offering a refined but approachable luxury experience. Read my trip report here.

The Barcelona EDITION — Barcelona
For something more design-forward, The Barcelona EDITION offers a sleek, modern contrast with a strong sense of place. Located near El Born and the Gothic Quarter, it features curated interiors, a lively rooftop bar, and a social atmosphere that blends seamlessly with the city’s creative energy. Read my trip report here.

Mastinell Cava & Boutique Hotel — Vilafranca del Penedès
If you’re looking to immerse yourself in wine country, Mastinell is a standout. Set among the vineyards, the hotel’s architecture is inspired by stacked cava bottles, immediately grounding you in the region. Rooms overlook the vines, and the on-site restaurant focuses on local cuisine paired with their wines. It’s a peaceful, design-driven escape and a perfect base for exploring Penedès more deeply.

Where to Drink Wine & Cava

Bottles of cava aging on the lees.

One of the most rewarding parts of visiting Penedès is discovering just how diverse and terroir-driven cava can be. I always recommend a mix of producers to understand the full range of styles, from fresh and approachable to more structured, age-worthy expressions.

A thoughtful introduction to the region
Avinyó is a wonderful starting point, offering elegant, balanced cavas and still wines with a focus on indigenous varietals. Not only is their cava special, but they produce one of our favorite bottles to have on hand for hot summer days: Avinyo Petilant. It’s a crowd pleaser, crisp and refreshing with a slight effervescence and floral note.

Raventós i Blanc builds on that foundation with more terroir-driven wines, known for their precision and mineral character, often compared to grower Champagne in style.

For a deeper dive into terroir and technique

Producers like Recaredo and Gramona showcase a more technical side of cava. Recaredo focuses exclusively on biodynamic, Brut Nature wines that are structured and deeply expressive, while Gramona is known for long-aged cuvées with richness, texture, and remarkable depth.

For setting and sense of place
And for a more relaxed experience, Llopart offers a beautiful hilltop setting with sweeping vineyard views, producing organic cavas that lean slightly more fruit-forward while still maintaining elegance and balance.

Where to Dine

Tuna with tomatoes and olives, paired with old vine Carignan at Dos Pebrots.

Barcelona is one of those cities where you can eat incredibly well at every level. From lively tapas bars to Michelin-starred dining, there is no shortage of fabulous restaurants.

Bar Cañete — Barcelona
A high-energy tapas bar that consistently delivers some of the best traditional dishes in the city. Expect expertly prepared seafood, jamón, and seasonal small plates in a buzzing, convivial atmosphere full of locals and tourists alike. Their motto is cheeky and fun … I won’t spoil the surprise!

Dos Pebrots — Barcelona
A more thoughtful, ingredient-driven experience, Dos Pebrots explores the roots of Mediterranean cuisine with a modern lens. The menu is creative yet grounded, making it a great option for a longer, more intentional dinner. Sit at the bar and watch the chefs in action.

7 Portes — Barcelona
For a more classic experience, 7 Portes is one of the city’s most historic restaurants and one of the most reliable places for a traditional paella. It’s a great way to experience the dish in a setting that feels both authentic and celebratory.

If you find yourself in wine country, there are a few excellent options worth seeking out:

En Rima — Vilafranca del Penedès
Located within the Hotel Mastinell property, this is a polished vineyard-side dining experience with seasonal Catalan cuisine and thoughtful wine pairings.

Vilagut — Vilafranca del Penedès
A refined, Michelin-recognized restaurant offering a more elevated take on local cuisine, perfect for a longer lunch or dinner between tastings.

Other Tips

• Plan for one full day in Penedès with a driver to comfortably visit 2–3 producers

• Pair your wine tastings with long, leisurely lunches. This region is as much about food as it is wine

• Consider structuring your trip Barcelona first, wine country second for a more relaxed finish

• Don’t overlook still wines! Many producers are doing exceptional work beyond cava

• Lean into the rhythm of Spain: late dinners, slow mornings, and unstructured afternoons are all part of the experience

  If all this talk of Spain has you jonesing for a good paella, you can find my recipe here after a trip to Barcelona last fall:

Barcelona and Penedès offer that perfect balance of energy and escape, where vibrant city life meets vineyard calm, and where some of the most exciting wines in Spain are still quietly under the radar. Salud!

Have you been to the Penedés region? Let me know in the comments any of your recommendations! And if you’d like to plan a trip here, please reach out below.

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One of the best ideas I ever had (and somehow convinced my husband and parents to join) was to go to Paris and Champagne for a long weekend over my 40th birthday in October. This was while he was secretly planning an elaborate Parisian-themed surprise party for me at home, no less which was an epic way to kick off birthday month.

It was the first time we decided to take advantage of direct flights to a major European city for a “long weekend,” and it completely scratched the itch of getting away without taking too much time from work or home obligations … plus, it was fairly reasonable. We’ve since returned to Champagne, most recently in Spring 2023, and both times of year are stunning. That said, if you go in the spring, you must stay a night in Paris—I mean songs have been written about this time of year for a reason.

At the end of last year, I wrote about my love affair with Champagne and went into greater detail on how it’s made, the grapes used, as well as favorites from a Champagne-focused tasting at my favorite wine shop in Chicago, Perman Wines. I also featured one of my top lunches ever at L’Assiette Champenoise, so I won’t go into detail here, but if that article was TLDR, just know this 3-Michelin-star restaurant features a cheese cart, an outdoor courtyard, and they ask if you’d like a “coupe” of Krug when you arrive (duh). See below for more info on the hotel that shares the address.

The train makes it incredibly easy to arrive in Reims from Paris. From there, you can rent a car or hire a driver to explore the countryside, spend a day in Épernay (another beautiful village in Champagne), or stay local and enjoy Reims itself.

Where to Stay

In full transparency, on our last two visits we rented Airbnbs. And while you may not often hear travel advisors advocate for short-term rentals, there’s absolutely a time and place where they make perfect sense. Heck, we even own and operate one.

The first Airbnb we rented was perfect for us. We were only there two nights, and it had an adorable courtyard, one bedroom, one bath, and an ideal setup in the heart of Reims. The second time, we were traveling with dear friends and while the views were stunning, there were a few quirks … for example, we each had our own bedrooms and bathrooms, but only one shared toilet tucked into a closet off the living room.

These are the types of details that can be hit or miss when you don’t know what you’re getting into, and a strong reason to use a travel advisor if you have any hesitation around accommodations. I work to establish relationships with hotels prior to and during your stay so there aren’t surprises, and if there are, I can step in and make things right.

All that said, when staying in Champagne, you’ll want to decide between being in the heart of Reims or Épernay, where you can walk to major Champagne houses along the iconic Avenue de Champagne, or opting for a more secluded vineyard retreat just outside the city.

Staying in Reims offers a slightly different experience than Épernay. It’s more of a cultural hub, with grand architecture, incredible dining, and several of the region’s most famous Champagne houses located right in the city.

Here’s where I plan to stay when I return:

Hotel L’Assiette Champenoise
More than just one of the region’s top restaurants, this is also a five-star, family-run hotel just outside Reims (though we walked back to the city center after our fabulous lunch on a perfect fall afternoon). Set within a peaceful park, the property pairs understated luxury with one of France’s most celebrated dining experiences, making it an ideal choice if you want to build your stay around a truly memorable meal. I need to experience the cheese cart again in my lifetime!

Les Crayères
Set within a seven-hectare park just outside the city center, this former family residence embodies classic French elegance. With just 20 rooms, impeccable service, and a two-Michelin-star restaurant on site, it’s one of the most refined stays in Champagne and feels worlds away from the bustle of town.

Château de Sacy
Château de Sacy offers a romantic countryside escape just outside Reims, set amongst rolling vineyards with sweeping views across the Champagne landscape. This intimate property blends historic charm with modern comfort, with thoughtfully designed rooms and suites that feel both refined and serene. The on-site restaurant highlights seasonal, locally sourced ingredients, paired with an excellent Champagne list, while the terrace is the perfect place to enjoy a glass at sunset. It’s an ideal choice for travelers looking for a quieter, more atmospheric stay that still feels deeply connected to the region.

Hôtel de la Paix (Best Western Premier)
For a more affordable option, this 4-star property offers a well-located and comfortable base in the heart of Reims, just steps from the cathedral, shops, and many of the city’s Champagne houses. The design blends contemporary style with a welcoming, easygoing feel. While not as boutique or destination-driven as some of the region’s smaller properties, it’s a reliable and polished choice for travelers who prioritize walkability and value in a central location.

Where to Dine

When it comes to dining in Champagne, the range is part of the fun.

For something casual, Le Glue Pot and Sacré Burger offer lively atmospheres with excellent Champagne lists, proving that great bubbles don’t have to be reserved for formal meals. And if you’ve never paired Blanc de Noirs with a burger, it will absolutely convince you that there’s a Champagne for everything.

For a more refined experience, Racine delivers a beautifully executed Michelin-starred tasting menu that pairs seamlessly with the region’s wines. Japanese influences are thoughtfully woven throughout the menu, and the wine list is excellent.

For something more local and intimate, stop for oysters at Le Bocal, or settle in at Le Chamois, a cozy raclette spot that is perfect for rounding out the experience, especially on a colder evening.

Where to Drink Champagne

One of the most special aspects of visiting Champagne is the ability to experience the wines exactly where they’re made, from historic maisons to small, family-run producers. I always recommend a mix of both to truly understand the region.

Ruinart — Reims
The oldest Champagne house, Ruinart offers one of the most beautiful and immersive tasting experiences in the region. Their historic chalk cellars, a UNESCO-listed site, create a striking setting for tasting their elegant, Chardonnay-driven Champagnes.

Taittinger — Reims
Recently reopened after extensive renovations, Taittinger is a fantastic introduction to Champagne. The experience walks you through Roman chalk caves and ends with a tasting of their refined, balanced wines. Their caves are also UNESCO-designated.

Champagne Pierre Péters — Le Mesnil-sur-Oger
For something more intimate, Pierre Péters is a standout grower-producer known for exceptional Blanc de Blancs from Grand Cru vineyards. Tastings here feel personal and focused, offering a deeper understanding of terroir and style.

Champagne Egly-Ouriet — Ambonnay
A favorite among sommeliers, Egly-Ouriet produces powerful, structured Champagnes with incredible depth. Visits are more limited, but if you can secure one, it’s a memorable contrast to the larger houses.

Avenue de Champagne — Épernay (Wild Card Experience)
Sometimes the best way to experience Champagne is simply to wander. Along the Avenue de Champagne, you can stop into multiple houses, enjoy a glass on a terrace, and soak in the history of the region at your own pace.

Other Tips

Look for highly allocated bottles from Georges Laval, as well as the prized wines of Marie-Noëlle Ledru, who retired in 2016 and produced exceptional Pinot Noir-based Champagnes, making any remaining bottles well worth their price.

We also have a special place in our hearts for Barrat-Masson, whom we visited in 2016. Their precise, biodynamic wines are a beautiful reflection of terroir and minimal intervention.

Finally, make a stop in Hautvillers to visit Dom Pérignon’s tomb in a small hillside chapel, which is a special way to remember where this all began.

Stay tuned for Penedés to finish off this series!

Want my help planning your next wine or Champagne getaway? Get in touch with me below!

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Note: My initial thought for this “OOO: Wine Week Away” piece was to share three of my favorite wine regions for a long-ish weekend or a week away. But as I started writing, each guide quickly expanded and I couldn’t help myself from including some of my favorite insider spots, restaurants, and wineries along the way.

Rather than hold back, I’ve decided to turn this into a three-part wine travel series this week. Today we start in Oregon’s Willamette Valley, followed by Champagne on Wednesday, and Barcelona + Penedès on Friday.

Each destination offers a slightly different way to experience wine travel, and I hope these guides give you a few ideas for your next trip!

Willamette (Dammit — IYKYK. If not, keep reading.)

Oregon wine country is one of my favorite spots in the U.S., mostly because of the serious wines paired with laid-back vibes.

I first visited the area after running the iconic Hood to Coast Relay race in 2012 and instantly was enamored. The stunning mountains that frame the region create crisp mornings with gentle breezes and warm, but not hot, sunshine. There are charming towns with inventive, locally sourced dining scenes that extend from Portland, world-class hotels, and of course, incredible wine.

There was an informal campaign years ago about the correct pronunciation of Willamette. If you sync it to “dammit” afterwards, that’s exactly how to align the pronunciation of the appellation.

Where to stay

Oregon wine country is a destination in and of itself. You can fly into Portland and head directly to Willamette, or stay a night in the city and drive out the next day. Regardless, you’ll want to determine whether you prefer a luxury vineyard retreat or a walkable town vibe to help guide your decision.

The Allison Inn & Spa offers a centrally located sanctuary just outside Newberg, and is surrounded by rolling vineyard views and 35 acres of gardens and farmland. Spacious guest rooms feature fireplaces, soaking tubs, and private terraces that invite you to slow down and settle into the rhythm of Oregon wine country.

The expansive grounds include vineyards and gardens that supply JORY, their farm-to-table restaurant. Their executive chef was just named a James Beard semifinalist for 2026, and JORY is one of the culinary standouts of the Willamette Valley. The restaurant is known for its seasonal menus that showcase local ingredients alongside an expansive and impressive wine list featuring some of Oregon’s best bottles. The Allison is ideal for travelers looking to pair serious wine exploration with a restorative luxury stay, and is perfect for a girls’ getaway or a couples trip.

The beautiful grounds at The Allison Inn & Spa.

For a more boutique feel, the Atticus Hotel, located in the heart of downtown McMinnville, feels like a love letter to the region. Each of its 36 rooms is designed around local artisans, makers, and producers. It’s an ideal base for wine travelers. You can walk to dozens of tasting rooms, restaurants, and shops on charming Third Street, while more than 200 wineries are within a short drive into the surrounding hills.

The hotel leans fully into its sense of place, greeting guests with local sparkling wine and filling rooms with thoughtful touches like fireplaces, locally roasted coffee, and Oregon-crafted details that make you feel instantly connected to the Valley.

Where to dine

Courtesy of The Painted Lady

Especially during peak season (spring through fall), I recommend securing restaurant reservations well in advance, as many book out several weeks ahead.

For an exceptional tasting menu, try The Painted Lady in Newberg. Open Thursday through Saturday, the multi-course experience inside a Victorian house is one of Oregon wine country’s most celebrated restaurants, and is often described as the “French Laundry of the Willamette Valley.”

Former Portland restaurateurs Eric Bechard and Emily Howard decided they wanted to be even closer to their farmers and opened Thistle, a 22-seat restaurant, in 2009. The menu is written on a chalkboard daily and often features locally baked bread, tartare, and pork chops, among other seasonal dishes. They also have a special collaborative wine with Goodfellow, one of my favorite Oregon Pinot Noir producers, available exclusively at the restaurant.

Stopping for pizza and a local beer is always a good idea after a day of wine tasting, and Capo in McMinnville is the place to be. Trained in authentic Neapolitan pizza-making techniques and sourcing ingredients from nearby farms, this locals’ hangout offers a great happy hour Wednesday through Sunday. Open after 4 p.m.

Where to drink wine

I’ve talked about my love for Brooks Winery during my Thanksgiving pairings (see here) and they should absolutely be on your radar to visit. The grounds are stunning, with mountains in the background, a lively tasting room with excellent food pairings, and weekly events that turn a tasting into a full outing. Don’t miss their dry Rieslings and my favorite Pinot, their Pommard clone.

Bergström Wines is one of the Willamette Valley’s most respected producers. This family-run estate crafts elegant, Burgundian-style Pinot Noir and Chardonnay from biodynamically farmed vineyards across several top appellations. Their wines beautifully reflect Oregon’s cool climate, volcanic soils, and the nuanced character of each site.

I joined their wine club years ago during my first visit to the region, and their wines age beautifully. In fact, I just rejoined!

Other tips

There are so many wonderful producers in the region, many of whom you won’t find in your local market. If you see anything from Antica Terra or Goodfellow on a menu or in a shop, just buy it.

Stay tuned for Champagne and Penedés later this week—cheers!

Want my help planning your next wine getaway? Get in touch with me below!

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Along the way, I’ve been fortunate to have wonderful mentors and leaders, both men and women.

Still, when you’re a solo entrepreneur, especially as a woman, it can occasionally feel a little isolating.

One of the things I’ve really appreciated since joining Fora is the opportunity to connect with other women building their own travel advising businesses.

Recently, I’ve been part of a cohort where we gather to talk through different topics related to growing our businesses, along with a separate chat channel where questions inevitably pop up throughout the week.

It’s been both empowering and incredibly practical to share ideas and gain insights from others navigating the same early stages of building something new. It’s also proven to be a wonderful resource as I develop itineraries for destinations that are new to me or that I haven’t visited in some time.

In honor of International Women’s Day this Sunday, today’s newsletter is dedicated to the ladies!

I’ll share a few destinations that are perfect for a girls’ trip abroad, highlight a company that specializes in solo women’s travel, preview a women’s retreat I’m working on with an old friend, call out some fantastic cruise voyages that offer no (or significantly reduced) solo supplements, and give a small update on a fun collaboration I’m developing with a Substack connection who now lives in Bologna, Italy.

The Best Girls’ Trips

Girls’ trip 2022 in Santa Barbara County

International Women’s Day always reminds me how important it is to celebrate the women in our lives.

Between busy careers, kids or no kids, aging parents, spouses, commitments, and the general pace of adulthood, it can feel like a miracle when a group of women, or even a mother-daughter duo, finds a few days that align to be together.

Honestly, the best girls’ trips are simply the ones you make happen.

I’ve planned or been part of several gal getaways over the years, and every one of them has been restorative, memorable, and just plain fun. I always return home more focused on my present life, with a full heart and usually sore cheek muscles from laughing so much.

A fabulous spa getaway to Kohler, Wisconsin (clearly in January).

As I’ve been thinking about my own milestone birthday this year, I’ve started to consider a few destinations abroad that would be perfect for gathering friends, celebrating a little, and creating the kinds of memories that make these trips so special.

As with any of my travel planning, I look to destinations where it’s easy to experience the culture through their food and wine. I also like to suggest walkable and safe cities anchored by stunning hotels and scenery.

Here are six international girls’ trips I’d plan right now:

Edinburgh, Scotland
A storybook city perfect for wandering together, with cozy pubs, historic streets, and dramatic landscapes just beyond the city.

Cartagena, Colombia
A vibrant Caribbean escape where colorful colonial streets, rooftop cocktails, and long seafood dinners await, plus a newly opened Four Seasons property.

Mallorca, Spain
An ideal mix of beach clubs, access to hiking and wine tastings, and incredible Mediterranean cuisine, making it easy to balance relaxation with exploration.

Copenhagen, Denmark
Stylish, walkable, and full of design-forward restaurants and wine bars, Copenhagen is perfect for friends who love culture, food, and a bit of Scandinavian chic.

Lisbon, Portugal
Lisbon offers sun-drenched scenery, incredible seafood and wine, and a laid-back atmosphere that invites slow wandering and late dinners together.

Gustavia, St. Barth’s
Chic boutiques, French-Caribbean cuisine, and sunset rosé by the harbor make Gustavia a glamorous yet relaxed destination for celebrating friendship.

Where have been some of your favorite trips with the ladies in your lives? Let me know in the comments!

Girls Guide to the World

I recently connected with Robert Belau, the CFO for Girls’ Guide to the World, a boutique company that provides small group tours specifically for women.

This powerhouse company was founded by his wife Doni, who started Girls Guide to the World 15 years ago as a love letter to Paris. She was spending extended time there, seeking out the locals’ favorites, and began organizing more and more girls’ trips, sharing insider access to her most coveted locations.

She then expanded to all of France, and over the years has grown the business to 85 trips a year to 40 countries.

The premise behind the company is strong.

As like-minded women, there are times we want a safe option for international adventures. What better way to explore than with locally sourced guides, especially if you’re traveling solo, your partner can’t (or doesn’t want to) get away, or you’re looking for a curated adventure with several friends or a mother-daughter duo?

The small group size of just six to ten women per trip allows guests to dine where the locals do, enjoy four- and five-star private accommodations emblematic of each destination, and have every trip led by a carefully vetted destination expert.

Robert shared that in pre-survey feedback, women most frequently say they’re apprehensive about not knowing anyone else on the trip.

In post-survey feedback, that ends up being the thing they liked the most, as they grow to appreciate the new connections.

Many end up coordinating future trips with women from their initial journey and stay connected through reunions and WhatsApp groups.

The itineraries are thoughtfully paced, allowing travelers to deeply experience each destination through its culture. Food and wine are at the forefront, which Robert noted is one of the best ways to understand a culture, and I couldn’t agree more.

At the same time, each itinerary includes a free evening so guests can explore independently or simply recharge their social batteries.

One itinerary that is particularly interesting is this women’s retreat in Bordeaux, “Harvest your Horizons,” led by founder Doni and a life coach. What better backdrop than sipping Cabernet from local women-owned estates, participating in a cooking class, visiting farmers’ markets, and incorporating coaching sessions along the way?

Reach out if you’re interested in learning more!

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Speaking of Retreats …

I’m working with an old friend from Chicago on our own women’s retreat!

Donna is an amazing culture change strategist, wine enthusiast, masterful facilitator, and leadership coach. Our husbands used to work together, and we gained the added benefit of friendship from that introduction.

Enjoying dinner and wine at Bern’s, our favorite restaurant.

While we are still finalizing the details, this high-touch, premium retreat will offer reflection and newly formed connections, then help translate that renewal into a clear plan for real life.

Our goal is for guests to feel refreshed and grounded while having time to enjoy the location’s best assets such as hiking, spa treatments, yoga, and wellness classes.

Currently, I’m deep into the location scouting process, searching for a space conducive to restoration, meaningful connection, and the ability to explore both on and off property.

Have you ever taken a retreat somewhere and loved it? Please share your insights!

Maybe Explora Journeys Is Right for You

The newly launched Explora Journeys campaign by McCann Paris caught my attention (and inspired the subhead).

As a former advertising gal, I appreciate when good marketing stands out in a sea of parity (pun intended).

Directed by photographer Jonas Lindstroem, known for his emotive style against stunning natural scenery for brands like Calvin Klein, Louis Vuitton, and Hermes, Explora’s new campaign asks whether the best hotel is really a hotel.

The idea of asking “maybe” is a gentle invitation for travelers to explore whether cruising could be right for them.

Their target market includes travelers new to cruising, and they currently offer an impressive list of voyages with no single supplement or just a 25 percent premium.

The vast majority of cruise lines price rooms based on double occupancy, so if you’re sailing solo, you’re often SOL. That has historically made cruises cost-prohibitive for many solo travelers.

A few voyages that caught my eye include:

🚢 San Juan to Miami on Explora III (November 1–8, 2026)
Featuring favorite ports like Tortola, Gustavia with a late 1:00 a.m. departure so you can enjoy dinner on St. Barth’s, St. Kitts, and Anguilla. This would be great for a solo journey or for traveling with a friend while still enjoying luxurious space.

🚢 Copenhagen Roundtrip on Explora IV (May 10–18, 2027)
A Baltic journey through charming Nordic ports including Helsinki, an overnight in Stockholm, Tallinn in Estonia, Ronne in Denmark, and returning to Copenhagen. This voyage offers just a 25 percent single supplement.

🚢 Barcelona to Rome on Explora I (September 6–13, 2027)
Bookended by two of my personal favorites, with stops in Ibiza, Tunisia, Malta, Taormina, and Amalfi. This journey offers countless opportunities to experience unique cultures, cuisines, and shopping, with a 25 percent single supplement.

Next week I’m meeting with one of the brand’s executives to learn more about their land partnerships, and the following week I’ll be touring their second ship in Miami.

More to come, as I think this will be a very approachable luxury option for experiential itineraries, tailored service, and an exciting alternative to large cruise ships without the price point of my personal favorite.

Two Substack Gals Meet in the Chat

Courtesy of

Last fall, while researching things to do in Bologna, Italy for a client traveling there in January, I came across Autumn in Italia, written by an American who moved from Savannah, Georgia to Bologna.

I loved her writing style and her tips for exploring the city known for its stunning porticos and one of the world’s oldest universities.

We started chatting and decided to partner up, and the collab is coming later this month!

She has shared two local recipes that I’m going to recreate stateside, along with some of her favorite things to do around Bologna.

To say I’m excited to try these recipes is an understatement. One is a slowly cooked sweet and savory onion appetizer that I think will be outstanding with some sourdough, and the other is a classic local pasta dish.

Stay tuned for more!

A Final Thought

Cheers to all the women in my life! I feel incredibly fortunate to have amazing female friends and role models, and to have found a supportive community as I build this next chapter.

As I’ve said, any career change is never easy but it’s more meaningful and rewarding when there are cheerleaders along the way.

As always, reach out if you’d like help planning your next journey.

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Enjoying our last sunset overlooking the BVIs.

I know what you’re thinking: Easy to say when you’re onboard such a luxury ship. And you’re right. But given how frequently my husband travels for work, he’s become rather discerning (as have I) when it comes to service and feeling comfortable away from home. The level of service, accommodations, and overall product on RCYC provide a familiarity and ease that allow you to settle in quickly.

Plus, with Bonvoy benefits, including points earned per dollar spent, credit toward annual nights, and the ability to redeem points for upgrades, this is quickly becoming our go-to cruise line.

We were actually onboard Ilma when they received the coveted Forbes Five-Star award, the first ever awarded to a cruise ship. The staff was overjoyed, proud, and humbled. With each congratulatory remark, their faces lit up. It was a beautiful reflection of the genuine care that defines the experience.

As much as I could go on about RCYC, there are many excellent cruise products worth considering.

I’ll be touring Explora II later in March, a brand gaining traction with its positioning as a luxury “hotel at sea.”

Windstar, the official cruise line of the James Beard Foundation (now entering its 11th year of collaboration), offers culinary-focused journeys featuring onboard chefs, wine tastings, and cooking demonstrations.

Viking continues to own the niche for adults-only, small-ship, in-depth itineraries across Europe, both ocean and river. And many more, with entrants from Four Seasons, Aman, and Orient Express.

With so many compelling options, how do you decide which cruise line is best for you? And more importantly, which itinerary?

Let’s walk through the matchmaking process I use to evaluate the best itinerary based on your travel goals.

Step 1: Align on Your Goal

Whether traveling by land or sea, the first question is always:
What are you hoping to feel during and after this trip?

Rested? Inspired? Adventurous? Connected?

Once we identify the emotional goal, we can begin narrowing down destinations or ports of interest. Often, clients are unfamiliar with many cruise ports (which is part of the appeal), but that can also make the decision feel overwhelming. Defining the goal helps filter the noise.

Crystal clear waters in St. Vincent & the Grenadines.

Step 2: Determine the Details

Once I understand whether you’re looking for exploration and relaxation or a once-in-a-lifetime adventure, we can hone in on logistics.

Seasonality plays a significant role:

• Mediterranean and Northern Europe sailings typically run May through September.

• Caribbean itineraries peak in winter and spring, with repositioning happening in fall.

• Alaska operates primarily May through September.

• Southeast Asia has optimal windows that avoid monsoon season.

• Expedition destinations like Antarctica operate within a very specific November–March window (who wants to experience the Drake Shake?!), while the Galápagos sail year-round but shift in tone between warmer snorkeling months and cooler wildlife-heavy seasons.

We also discuss:

• Duration

• Buffering at least one day before embarkation (and often one after disembarkation)

• Budget parameters

• Cabin preferences

From there, I narrow to specific cruise lines and voyages that align with your needs.

Side note: Repositioning cruises (also called “crossings”) can be an exceptional value. These sailings move ships between regions and often come at a significant discount with fewer passengers onboard. They’re ideal if your primary goal is relaxing and enjoying the ship. I even know of a couple where the husband completed continuing education during sea days (thank you, Starlink), then joined his family for dinners and evening fun.

Step 3: Evaluate the Itinerary

Both of our recent voyages had strong itineraries … but what made them stand out?

Using the framework above, it becomes a strategic exercise rather than an emotional decision.

For our February sailing, we knew we wanted:

• A relaxing winter escape

• New Caribbean islands we hadn’t previously visited

• At least one full sea day

• Ample time in port without feeling rushed

Here’s what ultimately won us over:

February Caribbean Itinerary

Day 1 – San Juan
Embarkation, set sail at 6:00 PM

Day 2 – At Sea
A full day to settle in and enjoy the ship

Day 3 – Canouan, St. Vincent & The Grenadines
8:00 AM – 7:00 PM (Anchored)
Signature beach club experience

Day 4 – Soufrière, St. Lucia
8:00 AM – 4:00 PM (Anchored)

Day 5 – Gustavia, St. Barth’s
12:00 PM – 1:00 AM (Anchored)
Late evening in port

Day 6 – Philipsburg, St. Maarten
8:00 AM – 8:00 PM (Docked)

Day 7 – St. John, USVI
8:00 AM – 7:00 PM (Anchored)

Day 8 – San Juan
Disembarkation, 7:00 AM

Sunrise over Soufriere, St. Lucia

Why This Itinerary Worked

What pushed us from “this looks good” to “book it” wasn’t just the destinations, it was the cadence and the cultural texture.

• A sea day immediately after embarkation set a relaxed tone from the start.

• A signature, all-ship experience on Day 3 eliminated decision fatigue early in the trip.

• Full days in nearly every port meant we weren’t racing the clock.

• A late departure from St. Barth’s allowed us to experience both daytime exploration and the vibrant nightlife.

• Anchored ports in scenic locations created a more intimate feel than docking in commercial terminals.

But beyond structure, I also evaluate itineraries through a culinary lens.

Does the routing include ports with distinctive food culture?
Are there destinations known for local producers or regional specialties?
Will we have enough time in port to experience them meaningfully?

St. Barth’s, for example, isn’t just a beautiful harbor. It’s a culinary destination with a strong French influence and an exciting dining scene. That late departure meant we could explore boutiques during the day and still settle into a proper dinner experience in the evening, something impossible with a standard 5:00 PM departure.

An itinerary shouldn’t feel like a checklist. It should feel like a well-designed week that leaves you rested and inspired.

Step 4: Finalize the Booking (and Maximize Perks)

Cruise line sales teams are knowledgeable and can assist with room selection and promotions.

That said, working with a travel advisor adds another layer of value.

Through my affiliation with Virtuoso, I have access to select “Virtuoso Voyages” across partner cruise lines. These sailings often include:

• Additional onboard credits (typically $200-$300, sometimes even more!)

• Exclusive onboard experiences (private cooking demonstrations, hosted cocktail hours)

• Special shore events

Recently, a friend had booked two Viking voyages independently. I was able to assume the bookings and apply $400 in added value simply by leveraging partner relationships, not to mention assisting with excursion strategy.

If you’ve booked a cruise within the last 60 days and haven’t paid in full, reach out. I can often add value retroactively.

Step 5: Perfect the Cadence of Excursions

It’s tempting to do everything in every port. That’s a recipe for exhaustion.

Instead, think of each stop as a preview. If something captivates you, such as a vineyard in Provence, a restaurant in St. Barth’s, or a historic city center, we can always build a deeper land-based trip later.

I aim to alternate active and restorative days, building a steady rhythm across the week. I often create a simple spreadsheet to visualize the cadence. On excursion mornings, we’ll order room service and linger in our robes before heading out. Those small pacing decisions shape the overall experience.

The “nature trail” is more like mountain climbing than hiking, but we still enjoyed it!

With so many options available, there are very few truly “bad” itineraries. There are only itineraries that aren’t aligned with what you’re hoping to accomplish.

The magic isn’t just in the ports you visit. It’s in how the week unfolds with the cadence, the culture, the time around a table, and the moments that make you say, “We should come back here.”

Now I’m curious: What has been your favorite cruise itinerary? Was it a specific port, a perfectly timed sea day, or something unexpected that made it memorable? I’d love to hear in the comments below!

If you’re thinking about cruising, I’d love to help you design an itinerary that feels less like a checklist and more like a curated journey.

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I couldn’t be more excited about some of the group travel work I’m doing right now. It’s so refreshing to be working in a creative capacity, leveraging years of research from long before I ever imagined starting a career as a travel advisor.

One of the best parts is that no two days are the same. I receive requests for all types of trips, airfare searches, wine tours, concerts, special experiences, and more. Some are as simple as booking a hotel and making sure my clients receive VIP treatment. Others are much more complex, involving multiple destinations or couples with very different ideas of what a perfect trip looks like. I love the challenge of designing itineraries that balance a wide range of preferences.

Today’s newsletter is all about one of the group trips I’m currently working on, what a DMC is and why I use this type of strategic travel partner in certain situations, and what my process looks like when pulling together all the moving parts of group travel.

NOTE: I’ll be enjoying a little “Vitamin Sea” next week, so it will be a bye week for the newsletter. You can follow along on my Instagram and Facebook Stories for some travel inspiration, and make sure to follow to check out my past posts.

I can’t wait to be back on the water!

Planning a 50th Birthday Getaway

One of my most recent requests was to create an itinerary to celebrate milestone birthdays for a small group of college friends and their spouses. They want meaningful experiences to ring in a new decade, not just another gift or party. There’s a shared bond that goes back decades, but everyone is now in different life stages. Still, they are coming together with a common purpose: celebrating years of friendship, growth, and the transition into a new phase of life, with all of its uncertainties and new adventures.

Some have young children, others have older kids. Some are navigating aging parents or health concerns of their own. There have been job wins, job scares, moves, and major life changes along the way. A trip like this isn’t just about celebrating a birthday. It’s about celebrating making it through the everyday.

While this particular trip centers on milestone birthdays, this same planning process applies to many of the group journeys I’m working on right now, including a women’s retreat, leadership-focused couples conferences, and multi-generational family travel. The goals may look different, but the underlying challenge is the same: designing an experience that balances diverse needs, energy levels, budgets, and expectations, while still creating something meaningful for everyone involved.

One lens that runs through all of these trips for me, no matter the group or purpose, is food and wine. I often start evaluating destinations based on how a place expresses its culture through what you eat and drink, whether that’s local markets, small wine producers, regional cooking traditions, or time spent around a table. For group travel especially, shared meals, wine tastings, and hands-on culinary experiences create natural connection points and become some of the most meaningful memories of the trip.

How I start planning a group itinerary

When I begin suggesting destinations for a milestone trip like this, I carefully consider a few key factors:

Ease of travel
Everyone is busy, and it can be hard to get away. A destination needs to be accessible for the majority of participants, especially when people are flying in from different home cities.

Range of activities
Some travelers want to golf, others shop, enjoy wine, hike, or relax. I’ll plan to offer several options so no one feels excluded. I also look closely at how a destination’s food culture and local wine producers can be woven into the experience, since shared meals and tastings tend to be the most unifying moments for groups.

Budget
Group travel almost always involves different comfort levels around spend. I look closely at accommodation flexibility, and destinations that allow personalization without creating noticeable gaps in the overall group experience.

Trade-offs
Every destination comes with trade-offs. In my project management days, we used to say you can have something good, fast, or cheap. You can pick two, but you can’t have all three. I see similar parallels in travel. A destination may be beautiful and affordable, but difficult to reach. A stunning destination that’s easy to access is rarely inexpensive. Or a destination may be more affordable because it falls in the shoulder or off season. I like to present options so clients can decide which levers matter most to them. Time away from work and family is precious, and there will always be some trade-off involved.

Process of elimination
Taking all of the above into account, I’m often left narrowing by region, hemisphere, or latitude to begin refining the shortlist.

What is a DMC and why do I recommend using one?

A DMC, or destination management company, is a strategic travel partner that works alongside me, not in place of me. They act as boots on the ground in a destination, whether domestic or international, though they are most often used for international travel. These are locally-based companies that help curate insider itineraries, allowing travelers to experience lesser-known cultural sites, authentic cuisine and wine tours, and special touches that aren’t duplicated over and over.

They know where to find the best hot chocolate in Paris that hasn’t gone viral on Instagram, where locals go for cicchetti in Venice, or the unknown but best quality markets in Barcelona. They also design custom experiences that online travel agencies and mass-market platforms simply cannot replicate.

A local’s market paradise in Barcelona.

DMCs can feel intimidating because of their depth of knowledge. That’s where I come in. I help narrow their focus based on what my clients actually want to experience and how they prefer to travel. I provide the direction, and the DMC creates a detailed, customized itinerary. We work as true travel partners to ensure the trip runs smoothly from start to finish.

I’ve recently started working with some highly specialized DMCs, including one that designs experiences specifically for families traveling with children. For example, a family might tour a well-known landmark, then return to a studio where the adults enjoy wine and cheese while the kids paint what they just saw. I love this approach because parents still get to experience iconic sites without ending the day completely exhausted, and children stay engaged without immediately retreating to their iPads.

One of the advantages of working with a DMC is that everything is packaged together. You receive one price for tours, transportation, and experiences, while hotels are often billed separately. One drawback is that pricing is less transparent, since it’s bundled rather than itemized. That said, we can usually estimate how costs are allocated by category and activity. I only work with vetted DMC partners with long-standing reputations and excellent client feedback.

They truly are worth their weight in gold when it comes to complex, multi-day and multi-city itineraries.

Sicily, Tuscany, Mallorca, French Riviera … or somewhere else?

Taormina with Mt. Etna in the background

Back to the creative part. Where should this birthday group travel?

These four destinations rose to the top because they all offer a strong mix of culture, food and wine, scenery, and shared experiences that work especially well for groups.

Sicily, Tuscany, and Catalonia were initial contenders. I’ve begun building a draft itinerary for Sicily that includes a villa outside Taormina, a day trip to Mount Etna, time to explore indigenous grape varieties like Nerello Mascalese, shopping in Taormina, a boat day to nearby islands, golf at one of Sicily’s top courses, and optional extensions in Ortigia (Siracusa), Malta, or Palermo.

I added Mallorca to the mix as a potentially more affordable alternative to Sicily’s island appeal. Tuscany is a classic, but it comes with a higher price point and may feel familiar to some couples who have already traveled there. The French Riviera offers fast cars, luxury sailing, Provençal vineyards and lavender fields, and a distinctly French coastal lifestyle.

Once we finalize a destination, I’ll bring in a DMC to refine the itinerary and layer in local experiences that only a true on-the-ground partner can provide. I’ll let you know in a future newsletter which itinerary we ended up going with!

Have you ever taken a trip to celebrate a milestone with friends or family?
Where did you go, and what made it especially memorable for you? Send me a note or sound off in the comments!

See you soon, well-rested and refreshed from the sea air and sun.

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Before diving in, a quick note. If you’re enjoying these weekly newsletters—I’d truly love to hear from you. Reply with feedback, tap a like, or forward this to someone you think might enjoy it. Your engagement helps me refine what I share and supports the growth of my travel business as I look ahead to expanding in 2026. Thanks!

My aunt Ruth and me arriving in Venice!

My First Trip Abroad

A trip like this required real lead time, especially in an era when booking platforms were nowhere near as sophisticated as they are today. I can only imagine the phone calls. There was no online booking with hotels, no easy way to compare itineraries or tour operators. My grandmother worked with my cousin’s maternal grandmother, who was a travel agent, to plan the trip, and as I’m embarking on a career as a travel advisor, I can appreciate her researching talents!

The journey began in Venice. I still remember stepping off the plane and boarding my first water taxi, completely awestruck by the light, the water, and the opportunity to explore such a beautiful country. Ahead of us were nine days filled with anticipation and discovery.

Our itinerary was full, but it worked. Each of us experienced it differently. My grandmother had already traveled extensively and would continue to do so for years after, including a final trip to Paris with her sisters just a decade ago. My aunt Ruth was an artist living in New York City, and together with my recent Renaissance art class, we tackled the Uffizi, which to this day is one of my most special memories with her. My cousin Rachel was a junior in college, her sister Maria a sophomore, and I had just graduated from Iowa and was working in telephone book sales (yes, phone books were very much a thing).

Each city brought discoveries not just about the destination, but about one another. We even assigned responsibilities. Ruth chose restaurants. Rachel documented everything in a detailed journal that I still treasure. Maria handled the accounting. I contributed art history and, I’d like to think, helped sniff out good shops. We referred to our purchases as “investments,” a term I’m sure my financial advisor father would view generously.

Reading back through the journal, it’s striking how many favorite moments centered on food. A particularly magical dinner stands out in San Gimignano at La Mandragola, where we stayed overnight and celebrated Ruth’s 50th birthday. There were twinkling lights, Tuscan air, local pastas, and the sense that we’d finally shaken off jet lag and settled into the rhythm of the trip.

Another unforgettable meal came in Verona before seeing La Traviata in the rain, when we enjoyed a delicious shredded meat dish, only to learn what it was after the server mimed a galloping horse and let out a little neigh (!!!). There was nightly gelato, always new flavors, and a boisterous final dinner in Venice that the other diners may not have found quite as charming as we did.

The Hardinger ladies in Verona.

Another favorite memory was our collective hunt for the perfect dress for Ruth’s upcoming wedding to her husband, Michael. To be able to share in that experience was something that we all treasure today, as we remember Ruth’s vivacity, humor (she tried on something Rowena definitely frowned at), and extraordinary style. This goes beyond just the little trinkets and other “investments,” we amassed, but brought us closer as a group of women, helping her enter into her forever with the love of her life.

What the Trip Still Teaches Me

First, stamina. My grandmother and aunt were unstoppable. This was not an itinerary for the leisurely traveler, but seeing the world through our first-time enthusiasm clearly fueled them.

Second, the importance of prioritizing family travel, especially as adults. We connected on a deeper level, and decades later, it remains a shared core memory, especially as life changes and shifts.

There were also lessons in figuring things out. The journal mentions wrong taxis, unvalidated train tickets, and navigating the Tuscan countryside without Google Maps. From those moments came confidence, the kind that only develops when you adapt and move forward.

We documented what we could, but we were present. Armed with disposable cameras, guidebooks, and journals, we didn’t capture everything, but we remember the moments vividly. Putting together an after-trip journal with stories and small details remains one of my favorite ways to preserve travel memories.

And finally, not losing the awe and wonder of travel. I’m sure we looked wide-eyed at so many moments. Watching that wonder in others is still one of the best reminders of why we travel at all.

Celebrating 100 Years

This weekend, our family gathers to celebrate Rowena’s 100th birthday, a woman who still seems to have plenty of gas left in her tank! Her own mother lived nearly to 112, and longevity clearly runs in the family. Some of my favorite memories are of her cooking, tending her huge garden in Albia, Iowa, and preserving vegetables to enjoy throughout the year. She traveled extensively with my grandfather, visiting countless countries, always returning with stories, slide shows, and often a doll for me.

Looking back over the last century at the discoveries, inventions, and changes, it’s astonishing. The world emerged from World War I, commercial aviation took flight, and many of the hotels and travel institutions we still admire today were born. See some of my favorites here.

This trip to Italy was just one chapter, but it set the tone. It shaped how I travel, how I think about hospitality, and why I believe certain experiences are worth prioritizing. Some journeys stay with you not because of where you went, but because of who brought you there and I’ll forever be grateful for this time together.

If you ever want me to help plan a special journey for you and your family, please reach out. You can connect with me on my Fora profile!

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Courtesy of The Vinoy

In preparation for my grandmother’s 100th birthday celebration, I did a quick search for significant openings and beginnings in the hospitality world. As I started researching, I came across a number of iconic brands that not only launched in that year, but have endured for a full century.

Florida Foundations

Courtesy of The Boca Raton

Within Florida, two legendary resorts trace their origins to 1926 and continue to define what thoughtful hospitality looks like today.

The Boca Raton

Originally opened in 1926 as the Cloister Inn under the Ritz-Carlton name, The Boca Raton has evolved into a destination encompassing five distinct hotel experiences: the Cloister, the newly renovated oceanfront Beach Club, the adults-only Yacht Club, the Michelin Key Tower with panoramic views, and the long-term stay Bungalows. Together, they share a common thread of Forbes Five-Star service, elevated design, and a private members club.

To mark its centennial, the resort has curated a slate of celebrations that nod to its origins. Highlights include a display of the original 1926 guest book (imagine the luggage, attire, and logistics of those early guests), a collaboration with Shafer Vineyards on a custom blend, the first in the winery’s 50-year history, an Assouline coffee-table book, a Roaring ’20s golf gala, wooden racquet tennis clinics, and even an outdoor opera. Each event celebrates the glamour and ritual of a bygone era.

The Vinoy Resort & Golf Club

Breaking ground in 1925 and opening just ten months later, The Vinoy welcomed its first guests on New Year’s Eve 1925. Located in downtown St. Petersburg, the nearly 400-room resort quickly became a winter retreat for the era’s elite. Rooms reportedly cost $20 per night, the highest rate in the country at the time, and the hotel operated seasonally from December through March.

After years of vacancy beginning in the mid-1970s, The Vinoy was added to the National Register of Historic Places and underwent extensive renovations to restore its original grandeur, complete in its pink splendor. Today, it’s a lively destination for locals and visitors alike, with strong dining, waterfront views, a spa, and a championship golf course. Rumor has it the property is haunted by a well-dressed gentleman. Visiting players facing the Tampa Bay Rays have reportedly seen him wandering the halls, only to disappear moments later.

Classic Hotels Worldwide

Le Bristol Paris

Courtesy of Le Bristol Paris

Paris has more than 1,600 hotels, roughly 100 of which carry a five-star designation, but few command the respect of Le Bristol. Opened in 1925, the hotel remains as relevant today as it was at its founding.

With a staff of roughly 700 employees, Le Bristol has long embraced a service-first philosophy, welcoming artists, dignitaries, actors, and royalty, perhaps helped along by its famously charming resident cat, Socrate. Despite its pedigree, the hotel is anything but stuffy. Pizza-and-Krug nights and DJ-led evenings draw a younger Parisian crowd alongside longtime patrons.

Once home to the American Embassy in 1940, and later to residents like Charlie Chaplin and Rita Hayworth, the hotel has preserved its quintessential Parisian decor. With an uncommon 50/50 split between rooms and suites, it retains a residential feel rarely found in modern luxury hotels. To celebrate its centennial, Le Bristol even released a custom Cluedo game (Clue in the States), a reminder that legacy can still feel playful.

Modes of Travel

Courtesy of trekandshoot

By Road: Route 66

Established in 1926, Route 66 connected Chicago to Santa Monica across more than 2,400 miles and eight states. The “Mother Road” became a critical artery during the Dust Bowl, shaping roadside dining, motels, and the culture of American travel.

Though decommissioned in the 1980s, Route 66 remains an enduring symbol of mobility and a reminder of how travel once unfolded at a slower, more deliberate pace.

By Air: American & Delta

In contrast to slow road trips, speedy commercial air travel got its launch in the 1920s. American Airlines traces its origins to 1926, beginning as a small airmail operation before evolving into one of the world’s largest carriers. Delta, founded just a year earlier, followed a similar path, growing from crop-dusting operations into a global airline.

While I certainly have my personal favorites today, what’s remarkable isn’t simply that these airlines have survived a century of change, it’s how profoundly they reshaped travel itself. Air travel compressed distance, redefined itineraries, and made international movement possible in ways that once felt unimaginable. Many of the hotels and destinations we now associate with modern travel exist because aviation made arrival both faster and more frequent.

A hundred years is a long time to do anything well and these brands have proven to have the longevity and legacy of staying true to themselves.

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