Greta was hanging on the steps of a train going about 60 miles per hour. A photo shoot, yes. Worth it? 100%. And that was only the beginning of her immersive trip to Sri Lanka.

Other highlights from our conversation were her newfound knowledge of the culture, learning how to use her thumb rather than a utensil on certain dishes, and the warm and welcoming people.

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Why Sri Lanka, why now.

As she shared on our video, Greta didn’t go looking for Sri Lanka. It came to her. Local partners on the ground invited her over to see the country first-hand, and she wasn’t about to say no. She had a scouting trip planned to India, so why not? “Sri Lanka kind of chose me, honestly,” she told me. Greta soon learned how easy it was to combine both beautiful countries into an amazing Asia adventure. And a great new recommendation for her luxury adventure-seeking clients.

What she found was a country that still feels like a discovery. Her word, not mine. It’s authentic in a way that’s getting harder to find, and the diversity surprised her more than anything. You can be on safari one morning watching Asian elephants and leopards, in the hill country surrounded by tea plantations the next day, and on the beach the day after that. She wouldn’t rush it that fast, but that’s the range packed into one compact country.

Then there’s the timing. The price point is still a real value for everything the country delivers, and the crowds haven’t arrived. Greta rarely ran into another American the entire trip. That’s the part that stayed with her, and it’s the whole reason to go now, before Travel + Leisure’s Top 50 nod for 2026 does what those lists always do.

Greta covered so much more in our 30-minute conversation, from the tea country to eating with your hands to the properties she couldn't stop raving about. Watch the full video above. But first, here are the questions people actually ask before booking Sri Lanka.

Discover Sri Lanka: From my Live on Substack.

Frequently Asked Questions About Visiting Sri Lanka in 2026

Is Sri Lanka safe to visit in 2026?

Yes. Greta felt very safe the entire trip and took the same precautions any traveler should abroad. Her advice is to book a private guide and driver, which handles the logistics and, as she put it, means the people showing you the country feel like family by the end.

Do you need a visa to visit Sri Lanka?

Yes, but it’s easy. Sri Lanka requires an ETA (Electronic Travel Authorization) that you apply for online before you go, for a minimal cost. It covers stays of up to 30 days; longer visits need a different visa.

How many days do you need in Sri Lanka?

Plan at least seven to ten days so you’re not rushed. That gives you time for safari, the hill country, and the beaches without cramming. Greta also recommends combining Sri Lanka with India, since the two pair well and it’s an easy nonstop flight between them.

What is the best time to visit Sri Lanka?

Sri Lanka is a year-round destination because the monsoons hit different parts of the island at different times. December through April is best for the southern and western beaches, while the east coast is better in the summer months. Greta went in May and still had great weather.

How do you get to Sri Lanka from the United States?

There is no nonstop flight from the US to Sri Lanka in 2026, so you’ll connect through a hub like Doha, Abu Dhabi, Dubai, or Istanbul. Another option is to fly nonstop to New Delhi, spend time in India, then take the short two-hour flight from New Delhi to Colombo, which is how Greta did it.

DOWNLOAD YOUR FREE RESOURCE GUIDE PDF FROM GRETA ⤵️

https://mailchi.mp/gretaandcotraveldesign/sri-lanka-luxury-safari-guide

Connect with Greta Meschke:
Founder, Greta & Co. Travel Design
Luxury Adventure Travel Specialist | Virtuoso Member
+1 314-221-6472
greta@gretaandcotraveldesign.com

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Thank you to everyone who tuned into my live video! Join me for my next live video in the app.

Get more from Robyn Levin in the Substack app

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I invited her to take us inside the experience and share what surprised her most.

Join us as we talk about:

• Why Sri Lanka is worth planning now, before it becomes everyone’s idea

• The list it just landed on, and why that matters

• Safari, minus the continent you’re picturing

• Why getting there is easier than you’d think

• The safety question everyone asks first

• How long to go, and the number that surprised even Greta

• What she’s still thinking about eating

Join us live Thursday, Aug. 20 at 2 p.m. ET: https://open.substack.com/live-stream/325958?utm_source=live-stream-scheduled-upsell

Hope to see you there!

Cheers,

Robyn

Long before Portugal became one of Europe’s hottest destinations, I was exploring the country. In 2015, I was already experimenting with a digital nomad lifestyle —years before it became part of everyday conversation.

Whether it’s travel, business, or technology, I’ve always been fascinated by what’s just over the horizon rather than what’s already mainstream.

I’ve never been interested in following trends. I’ve always been more interested in recognizing them before everyone else does.

That’s exactly what happened when I first heard about a brand-new luxury cruise line called Explora Journeys.

If you’ve been reading Rare Finds for a while, you’ve probably noticed a pattern. I’m rarely interested in the biggest, busiest, or most obvious choice. I’d rather introduce you to a remarkable place, hotel, or experience before everyone else discovers it. That’s become part of our journey together—and it’s exactly why I wanted to share this story with you.

Looking Back, the Signs Were Always There

When I launched Lux Club Travel in 2023, a friend suggested I combine two things I’d loved my entire life: travel and creating memorable experiences for other people.

The more I thought about it, the more I realized I’d been preparing for this role for decades.

At eighteen, while studying abroad in the Netherlands, I planned an entire three-week European adventure for my parents. We traveled through eleven countries using nothing more than a Eurail pass, paper maps, train schedules, and a sense of adventure. This was long before smartphones, Google Maps, or online booking sites.

My parents trusted me completely.

Thankfully, we had the adventure of a lifetime.

Looking back, I realize I wasn’t simply planning a vacation. I was creating an experience—the same thing I still love doing today.

Years later, when I owned an ice skating arena in South Florida, I often joked that I wasn’t in the skating business—I was in the business of Ice Cold Fun and Entertainment. Every public skating session, birthday party, competition, celebrity and special event was really about creating memories people would talk about long after they went home.

That thread has followed me throughout my career.

Today, I have the privilege of working with a select group of luxury travel partners who invite me to experience their hotels, destinations, and ships firsthand. They trust me to share authentic stories with travelers who appreciate exceptional experiences as much as I do.

One of my greatest joys is introducing people to places—and sometimes brands—they may never have discovered on their own. I suppose that’s been the common thread throughout my life. I’ve never been satisfied with simply following someone else’s recommendations. I’ve always enjoyed finding something special first, then sharing it with others.

Discovering Explora Journeys

When I first learned about Explora Journeys, the ships hadn’t even entered service.

That immediately caught my attention.

As part of the privately owned MSC Group, Explora wasn’t trying to become another luxury cruise line. They were reimagining what luxury at sea could feel like.

I interviewed members of the Explora team for my YouTube channel while the ships were still under construction.

Looking back, it’s been fun to watch several of those executives rise through the organization as the brand has grown.

Soon afterward, my Virtuoso host agency invited me to become an Explora Journeys Brand Ambassador after seeing one of those interviews. My enthusiasm for the brand was pretty obvious.

I was pre-selling Explora Journeys before the brand had even hit the water, organizing a small group for only the second voyage of Explora I—from Iceland to Copenhagen. I was fortunate to be invited aboard, and the experience exceeded every expectation.

I remember waking up that first morning somewhere between Iceland and the Faroe Islands, stepping onto my balcony with a cappuccino in hand. There were no loud announcements, no crowds rushing for lounge chairs, no sense of urgency. Just the sound of the sea, endless sky, and a feeling that this was luxury reimagined. It didn’t feel like a cruise ship. It felt like I was staying in a beautiful boutique hotel that just happened to be sailing across the North Atlantic.

The Difference Wasn’t One Big Thing

It was hundreds of thoughtful little things.

Luxury isn’t marble bathrooms or expensive champagne.

Luxury is intentionality.

I remember learning that the culinary team tested fifteen different pizza dough recipes before choosing one. Their sushi chefs trained in Japan. Every suite has a private terrace. There are no inside cabins. Even the language reflects the philosophy—you don’t stay in a cabin; you stay in a suite. You don’t take a cruise; you go on a journey.

With fewer than 1,000 guests, the ship never feels crowded. The crew quickly remembers your name, your favorite drink, and how you like your morning coffee.

Nothing feels accidental.

Everything feels carefully considered.

I sailed Explora a second time.

It confirmed what I’d already suspected.

This wasn’t simply a beautiful new ship.

It was a brand that genuinely understood the kind of luxury I value.

That feeling has only grown stronger. As I was finishing this article, Explora III was officially delivered — the halfway point in Explora Journey’s six-ship vision.

I Decided to Put It to the Test

There’s something I’ve learned over the years.

The best way to know whether you truly love something is to compare it with something else.

For years, I’d heard Regent Seven Seas described as one of the finest luxury cruise lines in the world. Friends loved it. Advisors praised it. Expectations were high.

So I booked a voyage.

Unfortunately, my experience didn’t match the reputation.

The ship I sailed was overdue for a significant renovation. My suite—and several others—lost air conditioning during the voyage. At one point, maintenance actually opened the ceiling in my room while trying to repair it.

The dining was average, but not memorable.

The biggest disappointment, however, was the itinerary.

The two marquee ports—the primary reason I booked the cruise—were canceled. I completely respect that safety comes first at sea, and captains make difficult decisions based on conditions. But it also became apparent that the age and limitations of the ship influenced what it could comfortably handle.

Even in the ports we did visit, we anchored offshore, boarded tenders, and then transferred to buses before finally reaching town.

None of those experiences alone would have ruined the trip.

Together, they changed the way I think about luxury.

Oddly enough, I’m grateful for that experience. Had everything gone perfectly, I might never have understood what I truly value when I travel. Sometimes disappointment brings clarity.

Continue reading as a paid subscriber to discover why that voyage completely changed my definition of luxury cruising, the three questions I believe every traveler should ask before booking, and why I’ll soon be sailing aboard the brand-new Explora III.

As a paid member, you’ll receive:

✓ In-depth hotel, cruise, and destination reviews I don’t publish elsewhere

✓ Behind-the-scenes conversations with luxury travel leaders

✓ Destinations Before the Crowds—discover remarkable places before most travelers do

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Editor’s Note: Two weeks ago, and I hosted a Substack Live about Croatia. During our conversation, I described myself as a “truffle hunter of travel.” The more I thought about it afterward, the more I realized it perfectly captured the way I’ve explored the world for years. This essay is the story behind that moment.

A couple of weeks ago, during one of our Friday Unstuck to Finding Your Edge Live conversations, I jokingly described myself as a “truffle hunter of travel.”

Jess laughed.

Then she asked me what I meant.

It made me realize that most people probably don’t know how truffles are found.

Deep in the forests of Croatia’s Istria region, highly trained truffle hunters work alongside remarkable dogs whose noses guide them through the forest, searching beneath the surface for one of the culinary world’s most coveted treasures—the rare truffle. Sometimes they uncover black truffles. If they’re especially lucky, they discover the elusive white truffle, prized by chefs around the world.

As I explained the experience during our Live, something clicked.

I wasn’t just describing a memorable excursion from my trip to Croatia.

I was describing how I’ve always traveled.

Not by following the crowds.

But by following my curiosity.

Curiosity Has Always Been My Compass

Most people begin planning a trip with a list.

The famous landmarks.

The restaurants everyone recommends.

The hotels that appear in every travel guide.

There’s nothing wrong with that.

But somewhere along the way, I realized the experiences I remember most rarely come from following someone else’s itinerary.

They come from asking one more question.

Accepting one unexpected invitation.

Taking a road that wasn’t part of the original plan.

That’s what led me to a family-owned truffle farm in Croatia.

Before we set off, our guide took one look at my leopard high-top sneakers, smiled politely, and handed me a pair of oversized black rubber boots.

As we followed him down muddy forest paths, the dogs darted ahead, noses to the ground, following a scent only they could detect. Every so often they’d stop, and we’d all gather around to see if they had found one of the forest’s hidden treasures.

Meanwhile, I was trying not to slip in the mud—or snag my powder-blue satin down jacket on the low branches overhead.

Let’s just say I wasn’t exactly dressed for a morning in the forest.

By the end of the excursion, I’d completely changed my mind about those oversized rubber boots. In fact, I jokingly asked the family who owned the truffle farm if I could keep them because they were, without question, the most comfortable shoes I’d worn on the entire trip.

They laughed.

I wasn’t entirely kidding.

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Looking Beyond the Guidebook

The truffle hunt wasn’t the only experience that stayed with me.

Curiosity led me to family-owned wineries where generations have been perfecting their craft, olive oil producers passionate about every harvest, and conversations with locals who shared stories no guidebook could ever capture.

Those moments reminded me that luxury isn’t always defined by five-star ratings or famous names.

Sometimes it’s found in the people willing to share their traditions, their passion, and their stories.

Those are the experiences I remember long after I return home.

Why This Story Stayed With Me

It wasn’t until Jess asked me what I meant by “truffle hunter of travel” that I realized I wasn’t describing one experience in Croatia.

I was describing the way I’ve traveled for years.

I’ve never been interested in simply checking destinations off a list.

I’m far more interested in discovering what’s hidden beneath the surface.

The stories.

The people.

The traditions.

The places that don’t always make the “Top 10” lists but somehow become the memories that stay with you the longest.

Looking back, it wasn’t really the truffles that stayed with me.

It was watching those remarkable dogs patiently search for something hidden beneath the surface while their guide trusted them enough to simply follow.

Travel has become much the same for me.

I don’t set out looking for the most photographed hotel or the restaurant everyone is talking about.

I follow my curiosity instead.

More often than not, that’s where I find the stories worth telling, the people I’ll never forget, and the places that become my own Rare Finds.

I’d love to hear from you. What’s one place—or one person—you’ve discovered that completely changed the way you saw a destination?

Thank you for joining me on this journey.

Cheers 🥂,

~ Robyn

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22 days. UK, Spain, Italy, Croatia.
Hosted stays including two nights alone on a floating houseboat in Split called Oasis Meu Amor. A storm rolled in the first night. I stayed. The boat was moving. The water was loud. I was completely alone.

And honestly? It was one of the best nights of the whole trip.

This is what luxury travel actually looks like when you stop waiting for someone to go with you.

I also sat down with the GM of Grand Hotel Brioni in Pula — one of the Adriatic’s most underrated five-star properties. He called me ‘Brand Ambassador for Croatia’ on camera. That interview is on YouTube now.

I had Merlot with Chef, Ana Roš at her brand new restaurant, Jaz in Croatia.

I shipped 12 pounds home from a tiny Croatian post office where nobody spoke English. The airline lost my bags for 8 days across 4 flights.

All of it is becoming a Croatia series — on TikTok and YouTube at https://youtube.com/@explorewithrobyn The full stories live here at Rare Finds.

Come follow along. Thank you for reading and watching!

— Robyn

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Most travelers heading to Croatia already know the names Dubrovnik and Split. And for good reason. They’re beautiful. Historic. Photogenic. Easy to fall in love with.

But on my fourth trip to Croatia in just two years, I found myself returning to a different corner of the country entirely: Istria.

And honestly? I think this may be where Croatia quietly becomes unforgettable.

Why Pula, Croatia Feels Different

Perched directly above the Adriatic Sea in Pula, Grand Hotel Brioni feels less like a flashy luxury resort and more like a beautifully kept secret. The kind of place seasoned travelers whisper about to friends after they return home.

The first thing you notice is the view.

The hotel rises directly from the cliffs above the sea, and the Adriatic here has that impossible clarity Croatia is known for — luminous blues, glassy water, and sunsets that make dinner reservations feel secondary. From my room, it honestly felt less like a hotel and more like being aboard a luxury ship without the crowds.

And then there’s the atmosphere.

Luxury here doesn’t scream for attention. It’s understated. Relaxed. Sophisticated without trying too hard.

That’s part of what makes Istria so compelling.

While southern Croatia often leans into dramatic coastlines and bustling tourism, Istria feels softer around the edges — more Italian in spirit, slower in rhythm, and deeply connected to food, wine, olive oil, and everyday beauty.
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Inside Grand Hotel Brioni in Pula

During my stay, I sat down with the hotel’s general manager, Alex Živković, who spoke passionately not only about the property, but about Pula itself — a city with more than 3,000 years of history and one of the best-preserved Roman amphitheaters in the world.

Most Americans don’t realize that Pula Arena still hosts major concerts today. Imagine watching global musicians perform inside a Roman arena overlooking the Adriatic.

That blend of ancient history and modern luxury is part of what makes this region so magnetic.

The hotel itself has a fascinating story.

Originally opened in the 1970s, Brioni was once considered one of the Adriatic’s premier luxury hotels — during a time when direct flights from New York actually arrived in Pula. After an extensive €50 million renovation completed in 2022, the property reemerged as one of Croatia’s most celebrated five-star stays, even earning recognition as one of the country’s top premium hotels.

But what impressed me most wasn’t the investment.

It was the restraint.

The renovation preserved the spirit of the original hotel instead of erasing it. There’s still a subtle vintage glamour woven throughout the property — a quiet nod to another era of European travel.
Learn more: 🏨 Book Grand Hotel Brioni →https://bit.ly/LuxClub-Brioni

The Sophia Loren Connection

And yes, there’s also the Sophia Loren connection.

According to hotel lore, Sophia Loren frequently stayed here during the Yugoslavia era and spent time cooking with former Yugoslavia president Tito on the nearby Brijuni Islands. Today, one of the hotel’s signature restaurants is named in her honor.

It’s the kind of story that could easily feel gimmicky elsewhere.

Here, it simply feels like part of the hotel’s DNA.

Why Food and Wine Lovers Should Visit Istria

What surprised me most about Istria, though, wasn’t just the scenery or the history.

It was the lifestyle.

The olive oil here is extraordinary — some of the best in the world, according to many culinary experts — and the wine scene deserves far more international attention than it gets. Add in truffle-rich cuisine, fresh seafood, warm hospitality, and a coastline that feels remarkably untouched in places, and you start to understand why travelers keep returning.

Including me.

The Spa, Infinity Pool, and Adriatic Views

And then there’s the spa.

Grand Hotel Brioni has quietly built one of Croatia’s standout wellness programs, including a striking infinity pool that visually spills directly into the sea and an indoor seawater pool heated year-round. In winter, guests can literally swim in warmed Adriatic seawater indoors while overlooking the coastline outside.

It’s thoughtful luxury.

Not performative luxury.

That distinction matters.

Who Should Visit Istria, Croatia?

Istria is especially well suited for travelers who love Italy, quieter luxury destinations, food and wine experiences, wellness travel, and immersive cultural experiences without the intensity of larger tourist crowds.

Why Istria May Be Croatia’s Most Underrated Luxury Destination

For travelers who love Italy but want something less discovered… for travelers who appreciate five-star hotels but not five-star crowds… for travelers who care as much about atmosphere as amenities…

Istria offers something special.

Luxury travelers may come for the Adriatic views, wine, and history — but it’s the warmth, hospitality, and pride of the people in Istria that keep many coming back.

And Pula may be one of Croatia’s best-kept secrets.

By the end of my conversation with Alex, I asked him why someone who had already visited Dubrovnik or Split should come here next.

His answer stayed with me.

“Curiosity,” he said. “Travelers always want to discover something new.”

He’s right.

And sometimes the places we remember most aren’t the ones everyone told us to visit first.

They’re the ones we almost overlooked.

Watch the full conversation with Alex Živković inside Grand Hotel Brioni.

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Robyn Levin is the founder of Rare Finds and Lux Club Travel, exploring cinematic stays and destinations before the crowds through editorial storytelling and behind-the-scenes conversations across six continents.

• Be prepared for more delays and lost luggage

• How to pack less for longer trips

• Mindset tips when things go wrong

• New EES — EU’s Entry/Exit System took effect April 10th, 2026. Expect longer lines at passport control. TIP: Fly into a smaller airport if it’s your first time entering the EU this year. I flew into Girona, Spain instead of Madrid — no line!

  
  Traveling this summer? Let us know where you’re going.

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THE LAST-MINUTE PACKING DECISION

I've always packed on the lighter side. Organized. Intentional. The night before this trip—a four-country journey mixing business, reunions, and a little vacation—I did what I always do: unpacked, reconsidered, removed things.

A pair of shoes. A favorite silk blouse. A few sweaters.

Last-minute decisions. The kind you make when you're trying to travel smart across a complicated itinerary.

Here's my question: Are you a heavy packer or light? And more importantly—do you actually know?

Because I'm about to tell you why the answer matters more than you think.

I never missed those pieces while my suitcase vanished for eight days.

But if they'd never found that bag, I would've really missed them.

LOST LUGGAGE AND LEARNED LESSONS

I've survived lost luggage before. Zagreb. Arrived from Florida in 17 degrees with nothing. The Esplanade Hotel saved me—dry cleaning, one spare outfit, grace.

I thought I knew lost luggage.

I thought I knew how to pack.

This month proved I didn't understand either.

I booked United months ago. Three flights to Birmingham for a conference. Simple routing.

Then United changed it. Then the third flight canceled at check-in. They rebooked me on KLM through Amsterdam.

Four flights now. Checked bag all the way through.

And for eight days, I had no idea where it was.

THREE ‘PARTNER’ AIRLINES AND ZERO COMMUNICATION

I called. I texted. I emailed. Stuck in a vicious loop between airlines and airports, each one blaming the other.

Try finding a human at Lufthansa in Germany. Try reaching KLM in Amsterdam. Email addresses online were wrong. Phone numbers didn't connect. And the bag services at each airport? They don't speak to each other.

So I stopped calling and started moving.

I had a conference to attend. Friends waiting in Oxford. Properties to preview. A mini-vacation planned. Ten nights in Croatia with my travel partners.

My suitcase wasn't going to reschedule my life. So neither was I.

WHAT THREE STRATEGIC SHOPPING TRIPS TAUGHT ME

I power shopped three times. First night in Birmingham—essentials. As soon as I saw the Uniqlo store— I dashed in and bought lightweight navy pants, a white top and socks. This international chain is an excellent store for emergency travel shopping.

Then in Oxford, where my friends showed me The Oxford Shirt Shop. I found two beautiful blouses. Pieces I never would've chosen if I had my suitcase.

They showed me their Oxford—the local lens. Brasenose College. The iconic hidden Turf Tavern, where Clinton famously didn't inhale and countless famous faces have lingered over a pint. A fabulous garden lunch in the Cotswolds.

By the time I got to Lake Maggiore, I'd given up expecting my bag to arrive. So I shopped again. Resigned. Moving on.

Then came the cosmic irony I didn't see coming.

My 25-pound suitcase arrived the night before May 1st—a major European holiday. Everything closed. No workday. Just chaos. And suddenly I had two trains ahead of me. Lake Maggiore to Milan. Milan to Lake Garda. The exact journey I'd dreaded most.

May 1st meant crowded platforms. Packed cars. Narrow aisles. Holiday travelers everywhere. And now I had to haul that suitcase through it all—the one thing I'd managed to live without for eight days.

But something had shifted. I hand-washed in hotel sinks those first eight days. Rotated what I had. Discovered I moved lighter, noticed more, felt freer.

I opened that suitcase when I got to Lake Garda.

And realized I didn't miss a single thing inside.

Fun fact: the Lake Maggiore hotel did my laundry better than I do. Still wearing those pieces from all three shopping stops. This is what traveling with intention actually looks like—whether you're checking a bag or carrying on. Checking out of my hotel, the idea occurred to me— maybe I’ll just send half of my luggage home! How ironic is that?

THE REAL TRUTH ABOUT TRAVEL AND RESILIENCE

Here's what seasoned travelers don't talk about: we pack the same way every trip. Same suitcase. Same routine. Same comfort.

Eight days forced me to ask the question I should've asked years ago.

What am I actually carrying? And why?

For six continents, I've traveled with the assumption that more is safer.

Turns out less is better!

Not because my bag was lost. But because losing it showed me I was already carrying too much.

WHAT I'M TAKING INTO MY NEXT JOURNEY

That suitcase taught me something I didn't expect. I survived eight days without it. Got it back. And now I'm holding both lessons at once—knowing I could make it without those clothes, and knowing the ones I chose actually matter.

Next dispatch: the properties that made this whole chaotic journey bearable and beautiful.

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I was planning a complicated multi-country European trip for myself and turned to ChatGPT for a little assistance with logistics and recommendations. I wanted new or renovated hotels near the coast in the Baltics. Not a popular request. Here’s how wrong ChatGPT can be — even using the latest models.

First, it raved about a renovated hotel in (2024) with a lovely spa and great views. It sounded like the perfect place. I took a closer look at the reviews online to get a sense of the vibe. Turns out, the hotel was very dated. Many guests complained about just how much it needed a major renovation. It hadn’t been updated since 2008. That’s a long time in the hotel business. Chat apologized, as it frequently does and said, “I should have been more careful with the research” and advised me to check the hotel websites for updates. There’s hope for website owners.

Next, I wanted a luxury boutique hotel in Lake Como, with easy access to a train station nearby. After hauling my suitcase up Venice’s cobblestone steps, I swore never to repeat that mistake. Italy has a way of turning baggage into a workout, as you may know.

ChatGPT enthusiastically shared a hotel that would be a perfect fit — just 2-minutes from the train station and on a quiet street. Perfect. I was all set to book. I started to look at trains from Milan to Lake Como. There was no such train station. In fact, I’d have to take a ferry from the train across the lake to get to the hotel. It’s amazing how convincing and wrong ChatGPT can be. Don’t be fooled. Definitely double check results.

So, back to square one and that’s how I found a travel expert in Italy. The old fashioned way of doing research, reading travel blogs and articles from real experts.

Do you have any stories where ChatGPT steered you wrong? Do share.

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Following up from my article last month on Where to Stay in Porto: 3 Picks from my 3rd Visit to Porto — here are four of my favorite towns — just a short train ride away.

The major publications covered the obvious choices beyond Lisbon and Porto. After four trips, I found four towns that are being overlooked—each worth a full day, each a one-hour train ride away, each revealing something different about how luxury travel is shifting in Portugal.

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First stop: Guimarães — where a boutique hotel owner schooled me on history… and my pronunciation;-) You’ll hear my language determination from the video below.

The gardens in Guimaraes are beautiful and the charming town is filled with tasty traditional Portuguese food, amazing architecture, quaint shops and friendly people. *You do not have to know the language, as most locals speak English.

The historic town centre has been listed as a UNESCO World Heritage Site since 2001, in recognition for being an "exceptionally well-preserved and authentic example of the evolution of a medieval settlement into a modern town" in Europe.

Fun fact: It’s said that Portugal’s first king was crowned here in 1139, making it literally the birthplace of the nation.

If you could hop on a train from Porto tomorrow, would you choose history, coastline, or food first?

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2nd: Viana do Castelo, Portugal — Where the River Meets the Sea
Viana do Castelo is 65 km north of Porto and about 50 km from the Spanish border.

Just a train ride north of Porto, you’ll be greeted with a stunning hilltop basilica with views stretching to Spain. The sea is 15-minutes away. I didn’t get to see it this time as my friend had mobility issues, however, next time I will definitely walk along the waterfront and visit nearby towns, including Caminha.

The town square in Viana do Castelo, Praça da República, is the heart of the city. Just a short walk from the station, it was surprisingly quiet despite the sunny August weather. I thought immediately: this is the escape I'm always looking for—cooler in every way. I wanted to keep this hidden gem to myself, but I’m sharing it with you — my valued subscribers.🤫

This region is known for its deep-rooted cod fishing history and is now renowned for its traditional Minho region costumes and intricate gold, which is still celebrated during the annual August festival, Romaria de Nossa Senhora d'Agonia. I visited the Costume museum which is quite special — you’ll get a real feel for their traditions.

What started out as a day trip turned into a research project — where to stay longer on my next visit. In fact, right now, I’m researching options for next summer. The convenience of the train makes it a great home base for exploring more towns in Northern Portugal and Spain. For me, that’s important, as I don’t typically rent a car — especially if I’m traveling solo.

3. 🎓 Coimbra: Beyond the Famous University

   1 hour 15 minutes from Porto

   💡 Fun Fact

   Home to one of the world’s oldest universities (1290) and the stunning Joanina Library with 300,000 ancient books. For a tour of the library, book your tickets online or in advance. Unfortunately, I wasn’t able to get a tour on the same day. Lesson learned.
   

   Coimbra had this fun, lively energy throughout—the kind you want to stay in the middle of. And I found exactly that at CBR Boutique Hotel. I’m always on the hunt to find unique, boutique luxury stays. I discovered this fabulous hotel right in town, filled with so much character and comfort. Trouble sleeping? Imagine, sleeping on a hand-crafted Hastens mattress, made of the finest natural materials, which I’ve never experienced before. No sleep aids needed to get a restful sleep on this luxurious bed!

   

   The Hastens brand is a 6-generation small family-owned company, which has expanded its markets to comprise 45 countries in Europe, Asia and America. The beds are still handcrafted with the same natural materials and the same spirit of excellence as when Pehr Adolf made his first beds 170 years ago.
   
   The beautifully designed rooms have every amenity you need, including a Bentley blow dryer. It was a cool product, but honestly too heavy for me.
   
   View hotel rates here: CBR Boutique Hotel — Hastens Sleep Spa, Coimbra.

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4. 🚣 Aveiro: More Canals Than Venice

   1 hour from Porto

   💡 Fun Fact

   Called “Portuguese Venice” but actually has more canals per square mile than Venice itself. It has a warm summer mediterranean climate.

   As a waterview lover, I was really excited to see this town. I also heard many expats were moving here. I actually got to me a couple who sold their house in Northern California to retire in Aveiro. They built a brand new home near the main town, at a fraction of the cost it would be in Ca. I was curious to see if this could be an option for me. After all, Portugal is been one of my top countries to visit in the last 10-years. Something keeps drawing me back — 4 - 5 times already.
   
   Aveiro is a walkable town and that’s how I chose to explore it. You could also take a canal cruise for an hour, but that’s very touristy. For activities, I highly recommend The Art Deco museum. It really dives into the history and movement of that time period. Check out activities and tours here.

   
   I stayed a beautiful, luxury boutique hotel right in town — Hotel Moliceiro, which is very convenient to restaurants and shops. The rooms are richly furnished and some have balconies. They accidentally gave me the wrong room the first night. I questioned the size of the room I booked and when they realized they made a mistake, the friendly man behind the desk politely asked if would be okay to be upgraded to the presidential suite. At first, I thought he was joking, but he was serious. What a nice touch! The room was fabulous — a two-bedroom suite with views overlooking the town. Lovely! Check out rates here for Hotel Moliceiro. Save for your future trip.

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Portugal is changing fast. These four towns won’t stay secret much longer. But for now, they offer something increasingly rare: authentic Portuguese life without the crowds — for now.

Save and share this article for your Portugal trip. rarefinds.substack.com/subscribe

• Some links are to products and services I’ve personally scouted, tried, and trusted. If you buy through those links, I may earn a commission at no extra cost to you.

Here are My Top 3 Picks in Porto, Portugal

1. The Yeatman Hotel, Vila Nova de Gaia- is a beautiful 5-star hotel across from the bustling Porto riverfront and near the iconic D. Luís I bridge. TIP: Take a stroll along this bridge to cross to the other side into Porto.

I stayed at the 5-Star Yeatman Hotel, a Virtuoso property with wine-themed rooms, amazing views and a relaxing spa. There’s several restaurant options onsite, including al fresco dining with spectacular sunset views overlooking the Douro river. The rooms are spacious and colorful. Most have large decks with stunning riverfront views.

View dates & rates here: https://booking.tpo.lu/WQ6Ecvu8

TIP: Ask the concierge for tickets to the WOW museum- a fun attraction in the cultural district featuring The Wine Experience, The Chocolate story and a large patio for entertainment and dining. You could easily spend a day or afternoon right there.

Vila Nova de Gaia, or Gaia as locals say, caught my attention while I was researching less-crowded areas in Porto. This region is not only home to many popular Port producers, including Graham’s (my personal favorite🍷), Taylor and Sandeman — Gaia is a fast-growing area for new housing and renovation projects.

Vila Nova de Gaia was slightly less crowded than Porto, however, I noticed a significant increase in visitors and temperatures lasts summer. I’ve been to Portugal five times now. I originally discovered Porto 10-years ago to escape two scorching heat waves, while living in Lisbon and the Algarve. Things are changing, as you know but Porto and Vila Nova de Gaia are two wonderful places to stay and play!

2. Caleway Boutique Hotel, Vila Nova de Gaia

I love finding unique luxury boutique hotels and the Caleway turned out to be just that! It’s in a beautiful historic building — a former police station. Notice the original stonework and intricate tiles in the photos below - amazing! I especially liked the little garden just outside the breakfast room. The rooms are spacious, comfortable and modern. The hotel has a 24-hour front desk — another excellent feature.

If you, like me, love walking— this hotel is perfect. It’s just a 2-minute walk from the Douro riverfront. Plenty of restaurants, shopping and activities nearby. The owners are very personable and even gave me a ride to the train station on departure day. The manager, Paulo is also very knowledgeable and helpful! That’s Paulo - below.

Click here to view rates and more and/or email: Info@calewayhotel.com Tell them Robyn from Florida referred you;-)

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3. Designer Airbnb - Bonfim neighborhood, Portugal

After extensive research and being a very particular traveler, I chose this beautiful restored townhome for our 1-week stay. The apartment is in a historic Art Nouveau corner building in “Os Duques” of Bonfim, Porto — “one of the 10 coolest neighborhoods in Europe”, per an article in the Guardian (2020). It was also ranked a “top four” coolest neighborhood in Porto.

Bonfim is a very walkable area with a few restaurants nearby. The apartment is about a 10-minute walk to the main squares in Porto. Perfect for a home base for exploring. I took the train 3-times during my stay to explore other charming towns 1-hour away. I’ll share those hidden gem towns and hotels with you in a future article.

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Our suite had 2 bedrooms and 2 1/2 baths. The main floor had a large bedroom and private bath with balcony access. The smaller upper bedroom also has a private bath - accessible by a little narrow staircase. If you’re looking for a spacious homelike stay —this would be a great choice. The apartment has every modern convenience including a small washer and dryer. We were greeted with freshly baked cookies, a fruit basket and Port — a lovely touch!

I sat down with the owners — a brother/sister team that worked tirelessly on this beautiful project for many years.

Address: 94 Duque da Terceira St.

In summary, these are my top 3 Picks if you’re visiting Porto, Portugal 🇵🇹.

• Some links are to products and services I’ve personally scouted, tried, and trusted. If you buy through those links, I may earn a commission at no extra cost to you.

The thing I worried about most was dinner. Big dining rooms, assigned seating, long tables full of duos and cliques — all the perfect ingredients for peak awkwardness. I nearly skipped that first meal and retreated to my cabin. Instead, I walked in, took a breath, and sat down.

Someone slid a chair back, smiled, and said, “Darling, we’ve been waiting for you.” His name was Mr. Levin — a warm, charming steakhouse owner from San Francisco who, hilariously, shared my last name. In five seconds the anxious fog lifted. Conversation flowed. Laughter arrived. That single dinner turned a nervous, uncertain trip into a voyage of discovery.

That night didn’t stop at a friendly meal. It changed my trajectory. Saying yes to that small, awkward moment nudged me into years of bolder choices: pioneering a six‑week digital nomad stint in Portugal in 2015, falling in love with its towns and people, and returning five times to share my favorite spots with others. What began as a nervous solo cruise became a pattern — lean in, say yes, and watch what shows up.

If you’re standing at the edge of something that feels a little scary, here’s what I’ve learned:

• Small yeses compound into big stories.

• The places you’re tempted to avoid often hold the best connections.

• You get braver as you get older — use it.

So next time you’re tempted to skip the room, skip the event, or click “not going” — sit down instead. Your next great story might be one “Darling” away.

Want to hear more stories from my Portugal returns or get a short list of my favorite hotels, cafés and beaches? Hit subscribe if you haven’t already.

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With wanderlust (and a little extra courage),
Robyn
Living bolder, older! 💫
P.S. Reply with your small-yes moment!

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Author’s note: I wrote this recap with sand still in my suitcase and a few jet-lagged memories fresh on my mind. If you’re new here, welcome! If you’ve traveled these wild routes with me before, I hope this year’s twists bring a smile (and maybe a little wanderlust) to your day.

🥂Wishing you a New Year filled with bold adventures, good health, and moments that surprise you in the best way. Glad you’re here!

Surprises, Soaring Moments & Serendipity

If you want to know how this year went, start here:
The UAE. A two-seater plane. Me at the controls—heart pounding, Arabian Gulf sparkling below, somewhere between terrified and thrilled.

That trip wasn’t some far-off fantasy—it was an instinct, years in the making. Ever since I handpicked that nine-port Middle East cruise (the one I mapped, planned, and got everyone excited for—before it was canceled), I knew I’d find my way there, one way or another. When the opportunity came, I went all in: six nights, four different five-star hotels—the Ritz (beach and desert), IHG, Anantara—each with its own story. I dove in, not just to the comfort, but into local culture: greeted by camels, sipping Arabic coffee poured from gold pots into delicate china, picnicking in a forest with a local guide, tasting dates so fresh they barely needed chewing. I was there to scout what’s next for travelers, colleagues, and luxury brands—but I left with a suitcase full of stories that felt entirely my own. Some I’ll be sharing here soon. A few stories from earlier journeys—Croatia and Montenegro among them—were published as features in Virtuoso’s Culinary and Wellness Newsletters.

Are you more of a beach lover, desert dreamer, or adventure seeker? You can have all three right here in # Ras Al Khaimah, UAE — less than 1 hour from Dubai. Stay tuned—the next stories might have you rethinking your own answer. Learn more and get exclusive offers at the Ritz, Al Wadi Desert. Ask me for details.

Luxury at Sea (Or, at the Mercy of It)

September brought my long-awaited Regent cruise—on a route with Bordeaux and Guernsey circled in red. Bordeaux, the headline act, was canceled at the last minute due to protests; my birthday toast happened with champagne on the sand in Deauville, France, with the International Film Festival swirling around us. Not a bad Plan B. Guernsey got canceled due to 8–12 foot swells in the English Channel. Cruising the Bay of Biscay had passengers running for Dramamine and wrist patches — selling out before dessert. Regent’s food? Surprisingly underwhelming, for all the hype. Portugal, though, as always, delivered: five visits in, still finding new corners and restaurants worth sharing.

Aruba’s Wind, TikTok, and Honest Impressions

Earlier in the year, I was tasked to help my family plan an all-inclusive vacation somewhere in the Caribbean. Aruba was the top choice by all involved. Though all-inclusive hotels are not my usual scene, I went along. We stayed at the brand new Hyatt Secrets in Baby Beach. The rooms were nice but the property is set back from the beach. So, if you’re like me and love an ocean view, unfortunately, your choices are limited. On arrival, I shot a spontaneous, wind-whipped TikTok video about the off-the-beaten-path location and what’s brewing on the island. That video? Over 11,200 views and 31 saves. Sometimes, a little authenticity and hair in your face are all it takes.

Wichita, Kansas: Surprises in the Heartland

This fall, I decided to attend a travel conference in Wichita—my first time in Kansas, and I was curious to see what I’d find.
After her talk, I was intrigued by the director of the local wildlife park and asked if I could film a quick interview. Only then did I discover she’s not just the director—she’s also the mom of Lucy, a baby kangaroo, who took turns on our laps while we filmed right there in the hotel conference room. I stand by my prediction: Wichita’s wildlife park is going to be an international draw. And Lucy? She’s already a star.

Life’s U-Turn: The Shortest Long-Distance Move

Of course, not all journeys involve airplanes. This was also the year I made what I now call my “shortest long-distance move.” In my 60s, I packed up decades in Florida, moved to Philly to reconnect with my roots and family—only to discover the city’s true personality: non-stop sirens, drag racing at 2 a.m., window-rattling bass, trash collection starting before dawn. And my family? Turns out, they really dislike driving into the city. After a few months of urban soundtracks and the world’s noisiest “luxury” apartment, I pulled a Life’s U-Turn—headed straight back to Florida. No regrets. Sometimes, the boldest move is admitting when it’s time to rewrite your map. Has that ever happened to you? Feel free to reply in the comments.

Stockholm: Serendipity at Its Best

Not all detours are disasters. I’d planned a post-cruise extension to Stockholm for a friend and client (his idea, not mine), spent days planning the trip, and then he had to cancel. What now? Excited from all my research, I went anyway and turned it into a solo scouting trip—checking out hotels, experiences, and a few connections I’d lined up. That’s how I found myself swept into a VIP three-day tour with a master guide who, as she casually mentioned, usually hosts prime ministers. Stockholm became the spark I never saw coming—opening doors straight to the UAE adventure that had been at the top of my list. Sometimes, you only discover what’s next by saying yes to what’s right in front of you.

If you want more of the stories behind the scenes—six continents, dozens of countries, wild detours, and what I’m learning along the way—you’ll find them in every issue here. Subscribe, stay curious, and let’s keep traveling a little ahead of the curve (and sometimes sideways) together.

Thanks for being here for the journey—twists, U-turns, and all. Have a story of your own wild detour? Hit reply or share in the comments; I’d love to hear it.

More soon,
Robyn
P.S — Watch my YouTube Travel Podcast — Explore with Robyn for more luxury travel insights and behind the scenes interviews.

I’ve always been a storyteller (age 3, if we’re counting), always the one asking questions, always ready to connect. These dispatches are where I share and spotlight what I discover — from tucked-away destinations and boutique hotels to on-location interviews with the visionaries who bring them to life.

Each edition brings together Stories, Stays, and Secrets — curated for discerning travelers, luxury brands, and advisors who want to see what’s quietly unfolding next, before it’s everywhere!

✨ What to Expect:

    •    🧭 Soulful, lesser-known destinations — before they go mainstream

    •    🛏️ Boutique hotel insights and behind-the-scenes interviews

    •    🎙️ On-location moments that reveal more than brochures ever could

    •    💡 Thoughtful reflections from six continents of travel, reinvention, and quiet boldness

This isn’t trip planning. It’s storytelling — curated with care, purpose, and a little edge.

⸻

👉 Subscribe to receive monthly dispatches

Partner with Robyn — Helping Hotels & Destinations Attract U.S. Travelers & Advisors
Email: hello@luxclubtravel.com

📍 Start with Dispatch #1: Portugal, Before the Crowd

Photo by Robyn Levin, Camilo Beach - Lagos, Portugal

Ten years ago, I was living the digital nomad lifestyle before it was a trend and discovered Portugal before it topped everyone's must-visit list — all because my dream home became a construction prison

The $58,000 Shock That Changed Everything

The $58,000 special assessment notice hit like a physical blow. My hands were shaking as I stared at the number.

Nine months earlier, I'd bought my dream waterfront condo in Florida—18 stories of 1970s charm with sweeping views and enough natural light to make me believe in fresh starts. I had plans. Big plans. Starting with a complete kitchen renovation that would transform the space into something worthy of those incredible sunsets.

The $58,000 assessment killed those dreams instantly. And that was just the beginning.

By July, they'd boarded up every window and door. The building's first major renovation since 1974 had begun, and I was trapped inside what felt like a construction war zone. Jackhammers started before sunrise. Backup alarms from trucks echoed through concrete walls. The Florida heat was suffocating, and there was no light, no air, no escape.

I sat in that sealed tomb, watching my view vanish and my renovation dreams crumble, when something inside me snapped. I needed an escape plan — something that would offer clarity, calm and a coastal paradise.

A Serendipitous Conversation Changes Everything

One week later, at a party in Sarasota, I met a woman who'd just returned from somewhere I'd never heard anyone talk about.

"Portugal," she said, practically glowing. "I stayed in Lagos."

Lagos. The exact coastal town I'd been quietly researching online, drawn to photos of golden cliffs and turquoise water.

I've learned to pay attention when the universe whispers. Sometimes it whispers through $58,000 construction nightmares. Sometimes through chance conversations at parties. But here’s where timing became everything: her friends had just committed to a year-long lease on their Lagos apartment and were considering a sublet.

The handover had to happen within five days — they were only available for 24 hours to show me everything before departing for their own adventure.

I bought my one-way ticket that night.

When Everything Goes Wrong Days Before Departure

Five days before departure, as if the universe wanted to test my resolve one final time, an unfamiliar ache in my mouth turned into something I couldn't ignore. My dentist squeezed me into his endodontist, but not until the end of the day. I was getting nervous, alone, and my phone battery was nearly dead. No one knew where I was.

Finally, when the doctor saw me, I asked for Valium. "Too late," she said, "but I'll numb you a lot." She handed me goggles to watch TV, then placed a rubber mat on my chest. "That's to make sure you don't swallow any instruments!"

I began to panic as the extra dose of novocaine penetrated my system. My heart started racing. All numbed up, I grabbed the chair handles, hoisted myself up, and ran out of the office, apologizing that I couldn't do this without Valium. I ran out with a prescription to the drug store.

When I looked in the mirror, I was shocked—my face was twisted like I'd had a stroke and I couldn't speak. Air pockets filled the space. I was able to communicate with the pharmacist, who held back her laughter and said her husband was a big baby at the dentist too. My dentist called to check on me and explained I'd had a reaction to the novocaine. "Come back at 8 AM, but take your pills first."

Now relaxed, I was the ideal patient and only asked her to put the temporary crown on tight to last six weeks. I was headed to Portugal, and amazingly, it did last. One week after that serendipitous conversation, still nursing my tender jaw but with my courage restored, I was on a plane to Portugal.

In my 50s, I was embarking on my first solo international luxury travel adventure, with an apartment sublet booked for four weeks, leaving a few weeks unplanned for exploration, and about to become a digital nomad trendsetter long before remote work was mainstream or "digital nomad" was even a hashtag.

This wasn't about becoming a "digital nomad" — that wasn't even my goal. As someone who's always spotted emerging opportunities (I'd been teaching LinkedIn strategies on YouTube since 2009), I sensed I could blend my marketing expertise with authentic travel storytelling in ways others weren't doing yet. I just didn't expect a construction nightmare to launch me into that future — ten years before Portugal became the hottest destination on everyone's list.

Portugal Before the Instagram Crowds: What I Found in 2015

I arrived in a Portugal that doesn't exist anymore. This was before Lisbon had QR codes in every café, before Porto's rooftops had waitlists, before Instagram discovered the Algarve. Church bells still marked time. Mornings were soft with salt air and blessed silence.

That 24-hour handover was like a crash course in Portuguese living. Two women, speaking rapid English mixed with animated Portuguese, walked me through the intricate dance of daily life in the Algarve. The apartment keys were an engineering puzzle — three different locks, each with its own personality and required technique. They showed me a quick tour of the town, how to coax the WiFi into cooperation and how to take the secret dirt path shortcut to town — mostly reserved for mopeds.

When the ladies mentioned I’d need to take a bus from Lisbon to reach Lagos, my jaw dropped. The thought of cramming into some crowded, questionable vehicle for three and a half hours felt like another obstacle in an already challenging journey.

But then they explained: This was a luxury bus with WiFi, spacious seating and even an onboard coffee cart. Three and a half hours of Portuguese countryside rolling past my window while I worked remotely with reliable internet — sipping Portuguese coffee (and later, Port!) I was already living the digital nomad dream before I reached my destination.

But nothing prepared me for what I’d actually rented sight unseen.

Living Above Paradise (and a Cemetary)

The apartment was perched above the sea with incredible light — but when I first stepped onto the balcony after my long journey, I was completely unprepared for what lay below.

Hundreds of whitewashed tombstones and crypts stretched out beneath me. An entire above-ground cemetery I’d had no idea existed.

The silence was almost deafening after months of jackhammers and construction chaos. I stood there, phone in hand, and called my cousin.

“Am I crazy?” I asked her. “I just arrived in Portugal by myself, sublet an apartment for a month and I’m literally living above a cemetery.”

But as the shock wore off, I realized something profound: I had asked for quiet after months of construction hell, and Portugal had delivered. Literally. The most peaceful neighbors imaginable.

But even paradise has its quirks. My "sea view" required binoculars to actually see the ocean. The roads were so narrow I had to press against buildings to let cars squeeze by. And every morning at 4 AM, the loudest seagulls on earth staged what sounded like territorial warfare outside my balcony — feathers everywhere!

Still, after Florida’s construction prison, it felt like heaven.

Finding My Sanctuary: The Luxury Hotel Discovery

After two weeks of restless nights and unreliable air conditioning, I knew I needed a change. I researched luxury boutique hotels in Lagos and found one with soundproof rooms, a small rooftop pool, and restaurant. After Florida's construction prison, this felt like the sanctuary I'd been seeking.

The Heat Wave That Led to Porto

Portugal decided to match Florida's summer fury with back-to-back heat waves, but at least I was now in a proper sanctuary. The luxury boutique hotel in Lagos had solved my noise and comfort issues, but more importantly, it became my introduction to authentic hospitality storytelling.

Two weeks after arriving in the Algarve, I started filming on-location video interviews with the hotel owners and managers. What began as curiosity (and honestly, a way to stretch my budget after that financial shock) became my first taste of luxury travel brand partnerships.

That's where I met Carlos.

Dining solo one evening (a skill I was still mastering), this kind Portuguese man struck up a conversation in careful English. He had three daughters and genuine curiosity about my story. When I mentioned the heat, his face lit up.

"Have you been to Porto? It's cooler."

He pulled out his phone, showed me a hotel booking app, and pointed to a sea-view room near the ocean. I booked it immediately — four nights to escape the heat.

The next day: train, plane, Uber through a summer festival crowd. By evening, I stood on a new balcony with a coastal breeze and discovered my new remote office.

Digital Nomad Lifestyle — before it was a trend! Porto, Portugal

The Real Discovery: Reinvention at Any Age

While my longtime consulting clients back in Florida and California initially raised eyebrows about my Portugal experiment, the 6 AM emails kept arriving — thoughtful, on-point, professional. I was still crafting stories and landing national media coverage for entrepreneurs and luxury brands. The location had changed. The work hadn't.

But something deeper was shifting. I was pioneering luxury remote work from paradise — a creative risk-taker embracing new experiences that would define the next decade of travel trends. The video storytelling work I'd begun at the Lagos boutique hotel was opening new doors. I'd been creating content since my first YouTube video in 2009 (teaching LinkedIn strategies — 27,000 views and counting), but this felt different. More connected. More purposeful.

I thought I was escaping a construction nightmare.

Really, I was discovering that life gets bolder, not smaller, when you're willing to risk everything on a curiosity.

The Algarve in those days was still Portugal’s best-kept secret. Locals outnumbered tourists. Restaurants didn’t need reservations. The beaches weren’t Instagram backdrops but actual places where Portuguese families came to relax. I was living in what would soon become a digital nomad hotspot, but I had it almost entirely to myself — 10 years before the crowds discovered it.

🏖️The Moment Everything Changed

My first real taste of Portuguese kindness came during those early Lagos days. After exploring for hours, I was a little lost in the historic walled town and I stopped at a café-deli for directions to a beach I’d heard about — Maia Preia. A local customer named Ana overheard my struggle with Portuguese and smiled. As it turned out, I was actually asking for directions to the same beach she was headed to on her day off.

"Come," she said, waving me toward a chocolate-brown Renault convertible.

Ana, a restaurant co-owner, was headed to her favorite beach — and gave me an impromptu tour along the way. The beach was stunning: golden sand, thatched umbrellas, even an ice cream vendor trudging across the sand like summers on the Jersey Shore.

Sitting in that beach chair, toes in Portuguese sand, I launched my first travel blog right there. The WiFi was flawless. Portugal was built for travelers like me.

That night, I dined at Ana's family restaurant perched above Camilo Beach. The view stunned me. The seafood was unforgettable. Today, that same spot books out weeks in advance — but back then, I had it almost to myself.

That's when I knew: this wasn't just an escape anymore. It was a completely new chapter.

✨Why This Story Matters Now

Nearly a decade later, remote work is mainstream. Portugal is on every "best digital nomad and retirement destinations" list. Those quiet coastal towns are bustling with laptop-carrying travelers.

But here's what hasn't changed: the power of saying yes when life forces you to choose between staying stuck or taking a leap.

My Florida condo nightmare that devoured my kitchen renovation dreams became the catalyst for the richest decade of my life. I've since built relationships with luxury hospitality brands across continents, crafting their stories and highlighting unique experiences.

What started as an escape plan became a media platform for authentic travel storytelling — connecting discerning travelers with experiences that go far beyond the typical tourist trail.

The truth about resilience? It's not about bouncing back to where you were. It's about bouncing forward to where you never imagined you could go.

Sometimes the worst thing that happens to you becomes the best thing that ever happened to you — if you're willing to live bolder as you get older.

What's Next

Portugal was just the beginning. Through this newsletter, I'll be sharing the unfiltered stories from my decade of traveling — the destinations that changed me, the industry insights that surprised me, and the moments that proved it's never too late to completely reinvent your life.

You'll get behind-the-scenes perspectives on luxury hospitality, authentic destination spotlights from my visits and practical wisdom for anyone ready to live bolder as they get older.

This marks my fourth trip back to Portugal, where I spent two weeks based in Porto using slow train rides to discover three amazing coastal towns that still feel like secrets — places I’ll be sharing next in Rare Finds, my new Substack platform dedicated to luxury travel discoveries before they become mainstream.

This is my first dispatch, and what better way to launch than by celebrating the 10-years before anniversary of the journey that changed everything.

📬 Like stories like this?
Rare Finds is free — get curated escapes, on-location interviews, and soulful discoveries, always before the crowds.

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Robyn’s Quick Picks from That First Portugal Adventure

• Taste: Grilled seabass and vinho verde on Ana's terrace above Camilo Beach

• Touch: Glazed tile staircases that glimmer after Lagos rain

• Skip: Expecting Lisbon to be quiet (it rarely is now)

• Instead: Let southern Portugal's quieter rhythms reveal themselves slowly

• The Detail: That cemetery view apartment taught me peace comes in unexpected packages