While I’m no longer hosting monthly coffee chats (but you can still book a 1:1 travel call with me!), I’m excited to continue sharing these in-depth guides every quarter, alongside my monthly destination spotlights.

GUIDE TO THE SCOTTISH HIGHLANDS

Let’s talk about Scotland. This country has taken hold of my heart. It all started with a deep dive into the Cairngorms National Park while planning a retreat back in 2024. Since then, I’ve returned multiple times, exploring everywhere from Edinburgh’s classic streets to the storied beauty of the Scottish Highlands. But truly, my favorite way to see Scotland is by road.

The North Coast 500 is 516 miles of wild coastline, ancient castles, dramatic cliffs, and tiny fishing villages tucked deep in the Scottish Highlands. What makes the NC500 so special? It’s endlessly adaptable. From camper-van to boutique luxury hotels, or a high-low mix as I did, you can really go any style or budget.

In 2025, I set out on this adventure with a few friends, and it’s become one of my most memorable trips to date. I’m sharing my actual itinerary, including tips for every budget. Click the link below to download your copy of this beautiful new guide to start your daydreaming. I hope Scotland starts capturing your heart the way it did mine.

DOWNLOAD THE GUIDE

Other FREE Resources:

• Destination Spotlights (The latest: African Safaris, Canadian Wilderness trips)

• Build your own DIY Detour (Build a little adventure in your everyday week)

• View all Dare Guides (Santa Fe, Provence, Lisbon, the Dolomites, Bozeman, and more…)

I’d love to hear what you think! Has Scotland been on your travel list?

xo,
Sheryl

Here’s my guide to making the most of a family getaway to this truly special corner of Big Sky Country.

Where to Stay

In Bozeman:

• Kimpton Armory Hotel – Stylish, central, and a Bozeman classic

• AC Marriott – Modern, fresh, with mountain views

• RSVP Motel – Hip, Instagrammable, and walkable downtown

• Field & Stream – Warm, welcoming, and outfitted for adventure

• Bodhi Farms – For glamping or farm-style luxury

Paradise Valley:

• Sage Lodge – Luxe riverside retreat with stunning views

• Chico Hot Springs – Historic charm, hot pools, and quirky Montana vibes

Big Sky:

• Lone Mountain Ranch – Ranch vibes, cabins, and family fun

• The Wilson – Modern comfort right in the heart of Big Sky

• The Huntley – A classic with all the amenities and ski-town charm

Where to Eat & Drink

Bozeman:

• Blackbird – Wood-fired pizza and seasonal Italian

• Heist – Hip, creative cuisine and cocktails

• Revelry – Brunch, lunch, or dinner on the patio

• Shan – My go-to for delicious sushi

• Roly Poly Coffee & Wild Crumb – The best for coffee and pastries

• The Western – Elevated Western fare in a cool setting

• Montana Ale Works – Family-friendly, lively, and local brews

• MAP Brewery – Beer, bites, and Bridger views

• Bodhi Farms – Organic farm-to-table meals

Beyond Bozeman:

• Stacy’s (Gallatin Gateway) – Hometown steakhouse and honky-tonk vibes

• Horn & Cantle & Wild Caddis (Big Sky) – Upscale mountain dining

• Riverhouse BBQ & Corral Steakhouse (Big Sky) – No-fuss, finger-licking goodness

• Sage Lodge & Follow Your Nose BBQ (Paradise Valley) – Treat yourself in the Valley

• Campione, The Mint, & Fainting Goat (Livingston) – Worth the drive for great food and small-town Montana charm

What to Do

• Rodeo Nights: Catch the Valley View Rodeo (Aug 13, 20, 27 & 28 / 7–9 pm) or the Lone Mountain Ranch Rodeo (Tuesdays / 6–8 pm)—classic Montana fun.

• Fishing: Book a trip with Yellowstone Angler in Paradise Valley—legit pros for a reason.

• Live Music & Dancing: Two-step at The Westerner in Gallatin Gateway.

• Madison River Float: With Madison River Tubing in Bozeman—nothing says summer in Montana like floating down the river!

• Paddleboarding: Head to Hyalite Reservoir for cool water and epic scenery.

• Explore Yellowstone: Enter through Gardiner (the North Gate) for wildlife, geysers, and iconic park moments.

• Adventure Sports: Channel your inner marksman with shooting sports at Gallatin Sporting Clays in Three Forks.

• Hiking: Bozeman’s trail game is strong. Try the College M Trail, Drinking Horse, Grotto Falls, Emerald & Heather Lakes, Storm Castle, Lava Lake, or Beehive Basin.

• Downtown Bozeman Shopping: Don’t miss Main Street for boutiques, Western gear, art, and souvenirs.

What to Wear

Montana summer days are warm, but nights can cool off quickly. Layers are your best friend! Here’s how I’d pack:

• Daytime: Comfortable shorts or pants, tees or tanks, and a button-down shirt or light long sleeve for sun protection. Don’t forget your swimsuit for river floats!

• Evenings: Bring a cozy fleece, sweater, or denim jacket for cool nights and patio dinners.

• Shoes: Sturdy sneakers or hiking shoes for the trails, sandals for town and river days, and boots if you want to fit in at the rodeo.

• Extras: A wide-brimmed hat and sunglasses, rain jacket (just in case), and a bandana—handy for dust, sun, or a makeshift hair tie.

• Rodeo Nights: If you’ve got cowboy boots and a hat, this is the place to break them out. Otherwise, denim and button-downs are the local uniform. I usually wear my cowboy boots and hat, jeans or jean shorts, a pearl snap shirt, neckerchief, bolo tie, and some turquoise jewelry

Montana style is effortlessly practical—come as you are, dress for comfort, and you’ll fit right in. If you need a packing list or want advice on what to buy locally, I’m always happy to help!

Why August in Southwest Montana?

Because there’s just nothing like late summer here. By day it’s swimming holes, ice cream, and big blue skies. By night it’s sunsets and live music with the windows down. Before long, the school year hustle and bustle returns—but for now, let yourself soak up one last slice of summer magic.

Want to go? Let me know if you want a custom itinerary, packing list, or just some local insight.

xo,
Sheryl

This summer feels a little different, travel-wise. With my big “study abroad” adventure in Italy at the end of the year, I’ve decided to scale back on grand plans and focus on what truly grounds me: home, family, and the outdoors.

Last summer, I kind of felt like I missed a lot. I didn’t go to a single rodeo and wasn’t in town for the 4th of July celebrations in Bozeman. So this year, I’m making up for it. I want to be in town, cheer at the rodeos, and hit those beautiful big hikes.

Montana has parts I’ve barely explored, and those are also on my list. The Badlands, camping in the Little Snowies or the Belts, and someday pitching my tent in Glacier. If there’s a theme here, it’s soaking up sun, dirt, and as many wild skies as possible.

June = A Big Road Trip

June is focused on my two-week road trip (although shorter than last year’s three and a half week epic). I’m looping through Montana, Oregon, into Northern California, and back. I’ll get to spend time with my sister and my parents in their garden, savoring my dad’s famous pour-over coffee and relishing time with my family.

July = Horseback Riding & Field Parties

One more “trip” I’ve planned for the summer will be a horsepacking trip in July with Honor Equine. I’m doing a four-night pack trip into Yellowstone with Sydney (my amazing equine workshop collaborator from the past two retreat seasons). We’ll be deep in the backcountry, and I’m really excited for this adventure since I went on my first horsepacking trip 4 years ago.

I also snagged tickets to the Outstanding in the Field dinner with North Bridger Bison. (Let me know those of you who’ve been to one!) I’ll get to dine in the actual fields and camp under the stars there as well. If you know me, you know I’m already counting down.

August = Camping

My summer started strong with a camping trip for my daughter’s birthday over Memorial Day weekend. Our campsite was surrounded by clover, and fittingly, the birthday girl found a four-leaf clover upon arrival☺️🍀. It was beautifully situated steps away from the water and with expansive views of the Gallatin Range. I’m inspired to do this again in August, for my own birthday. At least one more camping adventure with my kids; that tradition is one of my very favorites.

September = England

In September, I’ll be helping my daughter Isabel settle in London for her studies. (She’s getting her Master’s in Architectural Conservation at the University of Edinburgh!) We’re going to take a bonus side trip to Inverness together, because when in the UK, I can’t skip the Highlands! Come October and November, I’ll be at home soaking up the last quiet weeks before Italy.

As you can see, for most of the summer I’m not jet-setting too far. This season, I really want to be present before things pick up in the fall. Fireworks in my hometown, s’mores by the river, mountain air, and just hanging out with the people I love most on my patio. It is a busy season for my clients, though, and I’m excited to live through them vicariously, watching the itineraries we planned together come to life!

Where are you headed this summer? Let me know below! Are you playing it close to home like me or going to some fun places? I’d love to know.

xo,
Sheryl

Last summer, I spent 21 days on the road in my van, Gypsy Rose, winding from Montana to Oregon and Washington, and then up into British Columbia and Alberta. Traveling through Canada’s vast, rugged beauty felt equal parts humbling and rejuvenating. It’s amazing how much soul you can find in a place with so few people (The same population as the entire state of California in a country bigger than the U.S., let that sink in!)

The Land of Wild Possibilities

What struck me most was how easily you can find real, immersive wilderness experiences here. British Columbia and the Canadian Rockies are iconic for a reason. You’ve got the glacier-carved peaks in Banff and Jasper, dense rainforests hugging the Pacific, and wildlife that seems absolutely unbothered by human presence. But that wild spirit runs coast to coast.

Canada is truly the land where you can spend a day hunting for fresh mountain air on a silent trail, spotting wildlife on your own terms, and recalibrating your sense of scale and time. Even better, most national parks tuck up near a city gateway, so you can balance cosmopolitan culture with off-grid adventure.

Dreamy Destinations for Every Type of Explorer

Clayoquot Wilderness Lodge, BC
High on my bucket list: This all-inclusive oasis is reachable only by floatplane or boat off Vancouver Island’s wild west coast. Picture safari-style tents with three Michelin keys, eco-conscious luxury, and total seclusion from the modern world. If you’ve ever wondered what a safari feels like before heading to Africa, start here. It’s the glamping of your wildest dreams, and there’s nothing like it in the U.S.

Fogo Island Inn, Newfoundland & Labrador
Another stunner, and one of only two other 3-Key Michelin properties in Canada, Fogo Island Inn was built to save the island itself. Every glass-walled room overlooks drifting icebergs. 100% of profits go back to the island, the staff shares in the financial success, and the menu is hyper-local and seasonal. It’s as close to a fairytale as you’ll find—and staying here is an act of preservation.

Campgrounds: The Unsung Heroes
Truth be told, what left the biggest mark was how impeccably maintained Canadian campgrounds are. Outside Kamloops, I pulled into a site so clean it felt zen. Perfectly raked gravel, stacked firewood, axes supplied, and not a hint of plastic in sight. It was camping in its purest—and most sustainable—form.

Jasper & Banff National Parks
Rolling into Jasper, I was bowled over by the landscape’s resilience after recent fires and by how quickly the land is bouncing back. Jasper and Banff aren’t just eye-candy—they’re public treasures, where little details (free parks, tourist discounts for recovery, encouragement to use local resources) speak to a collective stewardship and invite you to rekindle your own spark.

If you’d rather stay in a hotel: For a grand, old-school experience, the Fairmont Banff Springs sits like a castle in the mountains, with elegant interiors, multiple dining options, and a world-class spa. Fairmont Chateau Lake Louise puts you right at the edge of that legendary teal lake, and their newly renovated Basin Thermal Waters spa is next-level (adults-only, indoor/outdoor thermotherapy, and all the pampering you could wish for after a day of hiking).

The Northern Lights in the Northwest Territories
If you’re dreaming of viewing this Arctic light, consider a real-deal Northern lights adventure in Canada’s Northwest Territories. It’s more accessible (for North Americans) than Scandinavia. You can have the whole dog-sledding and incredible remote lodges experience. Just prepare for a journey often taking seaplanes to get there!

Quebec’s European Vibes
If France is calling but it’s more realistic for you to stay on this side of the Atlantic, Quebec’s Eastern Townships deliver. Manoir Hovey (a Relais & Châteaux gem) sits lakeside, offering country elegance, fine dining, and the feel of a tucked-away manor—not nearly as wild, but deeply restorative, like a countryside retreat in the middle of nowhere.

Why I Love the Canadian Wilderness

What I truly loved? The sense of shared custodianship, how every place invites you to participate in caring for the landscape. Whether you’re waking up in a Michelin-rated eco-lodge, a mountain castle, or in your van by a mirror-like lake, there’s a through-line of connection, care, and wonder. “Come see beauty,” Canada says, “and rekindle your own spark while you’re here.”

Ready to plan your own Canadian wilderness adventure? I’d be thrilled to share my favorite routes, must-see parks, or help you figure out if you’re destined for glamping luxury or classic campground bliss (or both!). And if Clayoquot or Fogo Island are calling your name, let’s get you there—I’ll be cheering you on every step of the way.

xo,
Sheryl

Summer travel is calling. Europe, Central America, Southeast Asia, that dream safari you’ve been pinning for years — people are booking, and packing lists are being made. I love this season. Summer travel is right at our doorstep.

But here’s what I need to say to you before you get swept up in the excitement: Please, please get travel insurance. Especially if you’re heading abroad.

I know. You’ve heard it before. Maybe you’ve even skipped it before and gotten away with it. But as someone who has witnessed the full spectrum of what can happen when a trip goes sideways — especially now working as a travel advisor helping people navigate the world — I’m telling you this with everything I’ve got: travel insurance is not a corner worth cutting.

The Trip Was Supposed to Be “Easy”

Here’s the myth I want to bust right out of the gate: that travel insurance is only for the big, complicated, risky trips. That you only need it for the expedition to Patagonia, not the villa week in Tuscany. Not the girls’ trip to Portugal. {something other than a cruise}

Wrong.

The “easy” trip is often the one that catches you off guard. You’ve let your guard down. You haven’t stress-tested your plans because it all seemed so simple.

I’ve seen a traveler miss an international connection because of a three-hour domestic delay and have to rebook thousands of dollars in flights and hotels on the spot. I’ve seen a woman twist her ankle on a cobblestone street in Italy and end up in a local emergency room with no idea how her American insurance would work (or if it would work at all). I’ve seen families stranded abroad due to weather events that nobody predicted. I’ve seen someone’s luggage disappear into the airline abyss for four days.

None of these people were doing anything extreme. They were doing what travelers do. And every single one of them was blindsided by costs and chaos they hadn’t planned for.

Why Americans Traveling Abroad Are Especially Vulnerable

Here’s a hard truth: most American health insurance plans offer little to no coverage outside the United States. Medicare doesn’t cover you internationally at all. And even plans that offer some international emergency coverage often require you to pay out of pocket first and then fight for reimbursement. Which is a nightmare when you’re sick, scared, and in a country where you don’t speak the language.

A medical evacuation — just the transport to get you to adequate care — can cost anywhere from $50,000 to $250,000 or more, depending on where you are and how serious the situation is. I’m not trying to scare you. I’m trying to make that number feel real, because it is real, and travel insurance can cover it entirely.

There’s also the reality of the world we live in right now. Political instability, natural disasters, airline chaos, and unexpected global events don’t wait for a convenient time. The ability to cancel, interrupt, or be evacuated from a trip due to situations outside your control is not a luxury — it’s protection.

This is where I want to talk about something that goes beyond the insurance policy itself.

When things go wrong while you’re traveling — and sometimes they do — having a travel advisor by your side is a completely different experience than being on your own. I’m not talking about a faceless booking platform or an automated chatbot. I’m talking about a real human being who knows your itinerary, understands the fine print of your coverage, and can make calls, troubleshoot rebookings, and advocate for you in real time.

When a medical emergency happens abroad, the last thing you want to do is Google “how do I file a travel insurance claim in Croatia.” When a flight gets canceled, and a cascade of connections falls apart, you don’t want to sit in a queue with hundreds of other stranded passengers while your hotel check-in closes. When a country issues a travel advisory that changes your entire plan, you want someone who knows the landscape and knows you.

That’s what I do. Not because I’m a hero, but because this is exactly the kind of support that makes travel something you can approach with confidence rather than anxiety. A good travel advisor becomes your on-the-ground anchor even when you’re thousands of miles away.

The Travel Insurance I Reccomend the Most

I’ve looked at a lot of travel insurance over the years. I would require every woman who went on a retreat with me to get it. And when it comes to recommending something to the people I work with, I’m not going to point you toward something I don’t genuinely believe in.

Faye is my recommendation. Here’s why.

It was built for the way we actually travel today. Faye launched in 2022 with a fresh, tech-first approach. And it shows. The entire experience lives in a clean, intuitive app. Your itinerary is tracked in real time. You get proactive alerts when a flight delay makes you eligible to file a claim. You can upload documentation and submit a claim right from your phone. Reimbursements go directly to a Faye digital wallet that works with Apple and Google Pay, so you can access funds mid-trip, not weeks later after you’re home and have already maxed out your credit card.

The coverage is serious. For international trips, Faye offers up to $250,000 in emergency medical coverage, which is substantially higher than many competitors. It includes emergency evacuation, trip cancellation, trip interruption, baggage care, travel delays, and even pet coverage.

The language is actually human. One of the biggest barriers to travel insurance is the fine print. Faye deliberately writes their policy documents to be understood by real people, not lawyers. Their pre-existing conditions coverage policy, for example, is a short paragraph — not 12 pages of exclusions and asterisks. Buy within 14 days of your initial trip deposit, be medically cleared to travel at the time of purchase, and you’re covered.

You’re not over-insured or under-insured. Faye offers one clean plan tier with optional add-ons, including Cancel for Any Reason (CFAR) coverage, rental car protection, and more. You choose exactly how much of your trip cost you want to protect. This flexibility matters, especially if your trip involves a mix of refundable and non-refundable bookings.

How Faye Compares to the Other Names You Might Know

There are solid options out there, and I want to be fair with you. Here’s how I think about the landscape:

Allianz is a name people trust; it’s been around forever, has strong claims processing, and offers an excellent annual multi-trip plan for frequent travelers. If you’re a business traveler or take three or more international trips per year, their annual plan is worth a serious look. The trade-off: their per-trip plans can feel more rigid.

World Nomads is the go-to for adventure travelers — skiers, divers, hikers, climbers — because it covers over 200 activities by default without a separate add-on. If your summer involves heli-skiing in New Zealand or scuba diving in the Philippines, World Nomads deserves a look. The gaps: it generally doesn’t offer a pre-existing condition waiver, and trip cancellation limits on the base plan are quite low, which matters a lot if your trip has high non-refundable costs.

Travel Guard (AIG) is a strong option for families with customization through add-on bundles. It tends to run pricier, and its Cancel for Any Reason reimbursement caps at 50% — lower than what Faye and others offer.

Faye sits in a category of its own when it comes to the experience of actually using the insurance. With the app, proactive claim alerts, direct-to-wallet reimbursements, and human support, these make a difference. And for international travel, that $250,000 medical coverage ceiling is a meaningful differentiator.

The Bottom Line

I’ve lived through enough Detours long enough to know that the unexpected isn’t the enemy. It’s often the catalyst for your greatest stories. But there’s a difference between a Detour that shapes you and a crisis that breaks you. And a lot of that difference comes down to whether you were prepared.

I view travel insurance as preparation. It’s not fear. It’s respect for how much this trip means to you, and for the reality that even the most beautiful, carefully planned journeys can take a turn.

My last PSA: Buy Faye before your next trip this summer. Get it within 14 days of your first booking deposit to unlock the full suite of benefits. And if you want help building a trip that’s thoughtfully planned from the start — including making sure all the right protections are in place — you know where to find me.

Now go make some fun travel plans!

xo,
Sheryl

Some of my fondest memories are tied to a dude ranch vacation:

• Watching my kids learn to ride

• Learning to cut cattle on horseback

• Supporting women to step out of their comfort zones

• Waking to elk bugling on an overnight pack trip

There is something special about time spent at a dude ranch, especially the way you find yourself letting your guard down, relaxing, and truly connecting with. yourself and your people. For me, dude ranches offer the best possible reset.

I spent the last 8 years taking women on ranch retreats in Big Sky. We spent our days horseback riding, taking fishing lessons, hiking, line dancing, and sharing stories around the campfire. (One year, we even went on an overnight pack trip!). Turning down that dirt road along the Taylor Fork and moving into my cabin for the week is something I’ve looked forward to each year, and will miss dearly. So, while I’ve hung up my cowgirl hat from hosting Detours, I still highly recommend a ranch experience to anyone who is interested! I’ve gotten many questions over the years about where to go, and now I’m finally spilling the beans on the top places I recommend for getting an authentic dude ranch experience in Montana.

Why Montana?

You can find dude ranches in Colorado, Wyoming, and other pockets of the West, but there’s no other vacation quite like Montana. Ranching has been a thriving tradition here for more than 130 years. It’s woven deeply into the land and the people. With our big skies, wide open valleys, snow-capped mountains, and rivers that wind through meadows, it just feels wild in a way you can’t experience anywhere else. The state’s unique blend of history, culture, community, and genuinely breathtaking scenery means ranch life here feels both timeless and vibrantly alive.

A Few Things to Know Before You Go

• Getting There: Most ranches are best reached via Bozeman International Airport (with a rental car or arranged driver). However, The Ranch at Rock Creek and Paws Up are closer to Missoula’s airport.

• Best Time to Visit: Summer is peak season for warm weather, full activity menus, and lively gatherings. (Book early to get this time!) Fall is my personal favorite, with epic foliage and fewer crowds. Some ranches offer special winter experiences, such as skiing and snowshoeing. April through late May is Montana’s mud and rain season.

• How Long to Stay: Five nights is the magic number. It’s long enough to sink into the ranch pace and try everything that calls to you. In summer, the most popular ranches may require a week’s stay.

• Packing Tips: You’ll want practical, comfortable layers. Jeans, sturdy boots, a wide-brimmed hat, and sunscreen, plus a fleece or denim layer for evenings. I always took my group to Murdoch’s as our first stop after the airport before heading to the ranch. They have everything you need! Need inspiration? Check my inspiration with “What I’m Wearing the Ranch” part 1 and part 2.

• Unplug & Connect: Many ranches offer limited cell coverage and Wi-Fi only in the main lodge. Lean into it!

• Tipping: Gratuities for wranglers and ranch staff are customary. Some ranches include this in your rate; others provide clear guidelines. Don’t be shy to ask.

What will your stay be like?

You’re not just a guest, you’re (temporarily) part of the team. The more you pitch in, the more you get out of the experience, whether it’s helping with chores, joining a cattle drive, or swapping stories with fellow travelers at communal meals. Ranch days are satisfyingly predictable: morning rides or activities, afternoons fishing, hiking, or relaxing, and long evenings lingering over firelight and family-style dinners.

What You’ll Eat (& Drink!)

Ranch cuisine is hearty and memorable. Some favorites you might encounter:

• Chuckwagon breakfast (eggs, bacon, biscuits cooked over open flame)

• Slow-roasted brisket, pork tenderloin, elk, bison, or wild boar

• Smoked or grilled local trout or salmon

• Rich chili verde & smoky ranch beans

• Corn pudding & warm fruit cobbler

• Cowboy cookies (the size of your palm, with oats and pecans)

• Classic “ranch water” cocktails: tequila, lime, and sparkling water over ice

My Recommended Montana Dude Ranches:

Luxury Ranches

• The Ranch at Rock Creek, Philipsburg, MT / All-Inclusive / Open All Year

• Paws Up Montana, Greenough, MT / All-Inclusive / Open All Year / 2 Michelin Keys

• Lone Mountain Ranch, Big Sky, MT / All -Inclusive / Open All Year

Mid-Level Ranches

• Nine Quarter Circle Ranch, Big Sky, MT / All-Inclusive / June - September / 6-night minimum

• Elkhorn Ranch, Big Sky, MT / All-Inclusive / June - September / 6-night minimum

• Mountain Sky Guest Ranch, Emigrant, MT / All-Inclusive / June - September / 6-night minimum

Budget/Adventure Ranches

• Circle Bar Ranch, Hobson, MT / All-Inclusive / June - September / 3-night minimum

• Chico Hot Springs, Pray, MT / Room-Only / All Year / 1-night minimum

• B Bar Ranch, Emigrant, MT / Room-Only / All Year / 1-night minimum

• Dreamcatcher Tipis at Yellowstone, Gardiner, MT / Bed + Breakfast + Campfire / May - October / 1-night minimum

Every property I recommend is committed to conserving the land and honoring Montana’s historic cowboy tradition. Some are working cattle ranches, others are pampering wellness retreats, but all connect you with the land (and your inner cowgirl or -boy).

Ready to Ride?

If you’re dreaming of wide-open spaces, starry skies, and days spent in the saddle, a Montana dude ranch could be just what your soul needs. I’d love to help you match your style (and budget) to the perfect ranch experience. Feel free to reach out with any questions!

Happy trails,
Sheryl

If you’ve been following along, you’ll know I’m in the midst of planning my own “study abroad” in Florence for the end of this year. This spring, the stars aligned for an Italian journey that was both my sister’s birthday trip and an opportunity for me to do some serious research for my upcoming Florentine semester.

Why Florence?

Aside from being the birthplace of the Renaissance (ummmm, no big deal, right?!), Florence is walkable, safe, and well located for easy exploration of Northern Italy and most of Europe by train. And, the Italian food scene is unlike anything I’ve experienced elsewhere. UNESCO’s recognition of Italian cuisine as an Intangible Cultural Heritage of Humanity reinforces food’s role as a powerful symbol of culture, connection, and storytelling, which I can’t wait to experience more fully. My list of restaurants I want to try keeps getting longer, not to mention the wine! Most importantly, I want to learn to speak Italian with confidence, and Florence offers exceptional language programs - there’s truly something for every type of language learner.

My mission for this spring trip was simple: find the best Italian language program for me, and determine where I’ll call home this winter. After touring a few options, Centro Machiavelli on the Arno River in the charming Santo Spirito neighborhood won me over. Accredited? Check. Great location? Double check. But what sold me was their 50 Plus program: four daily language classes plus 3+ cultural activities or mini field trips each week. The staff instantly made me feel at home, and I even met a fellow student from San Francisco (cute, age-appropriate, and yes, the universe does have a sense of humor). Unlike other schools I considered—which either weren’t as well organized, were located out in the sticks, or catered almost exclusively to 20-somethings—Centro Machiavelli draws a more diverse, international crowd (and not just college students). Feels like my kind of tribe.

A Sister Vacation

My sister’s last trip to Europe was a whole thirteen years ago, part of a whirlwind Italian family tour with ten of us (yes, ten) in tow. This time, it was just the two of us, which—shockingly?—is something we’ve NEVER done before. We set up base in Florence, unpacked, and immediately slipped into city life instead of living out of a suitcase. Having my sister with me made all the difference when it came to gut-checking my plans; she’s honest (sometimes brutally so), but always has my best interests at heart.

Turns out, we travel ridiculously well together! Her only non-negotiable was gym access with a treadmill (she’s training for a half-marathon), so our days naturally orbited around morning workouts and long walks, which meant hitting 15K+ steps a day, easy. I found her dedication inspiring. I might just have a 5K in my future! Our workouts paved the way for guilt-free Tuscan feasts every night, which we thoughoughly enjoyed. (See my Florence restaurant recs below.)

On occasion, I fell into the “big sister” role and over-explained or ordered on my sister’s behalf, something I didn’t even realize I did?! I also happily supported my sister as she stepped out of her comfort zone to drive a Vespa scooter around Chianti, all on her own, and helped her select some gorgeous Italian ceramic plates in honor of her 30th wedding anniversary. We both agreed that the time away from our day-to-day was so important, and being able to travel together was super special.

Florence Hits (and a Couple Misses)

Hotel Number Nine Firenze

Pros: Excellent gym, tasty breakfasts, solid location, and very gracious staff (truly, they went above and beyond).

Cons: The lack of a gracious lobby and gathering space bothered me, and the decor just wasn't my vibe. I wouldn't stay there again, but my sister absolutely would - she especially loved the gym.

The Social Hub

For my upcoming winter stay, I’ve picked The Social Hub. With 20+ European locations, The Social Hub is reimagining how we “do” hotels. They combine modern rooms, student accommodation, co-working spaces, a gym, a restaurant, a killer rooftop garden/bar, and even an Olympic pool with city views. Extended stay guests (like me) get a bike with their room. It’s slightly outside the city center but right by the train station, which will be amazing for day trips.

Pasta-Making Class

We learned how to make three different kinds of pasta, three different sauces, and chocolate gelato. Our chef instructor was hilarious and made the entire pasta-making process enjoyable and easy to understand. The group we were with was super sweet, including a couple on their honeymoon and grandparents traveling with two of their grandchildren. Chianti wine was poured all evening, and our shared meal was delicious.

Tuscany Vespa Tour

Bright and early Saturday morning, we met our guide by the Arno River on the east side of town and drove about 30 minutes outside of Florence to Chianti, where we all took a Vespa driving test. The test was surprisingly nerve-racking - one woman wiped out her Vespa entirely! No injuries, thankfully. Fortunately, both my sister and I passed. I absolutely loved ripping around the Tuscan hills on a Vespa - my sister, not so much, but she survived. We visited a small chapel built in the year 1000 on a hilltop, which a sweet elderly couple lovingly cares for. Olive trees were being pruned everywhere, and the cut branches burned in small fires amongst the orchards. We stopped to taste wine and enjoyed lunch overlooking the rolling hills and vineyards. The day was a perfect break from the hustle and bustle of the city.

Both activities were with Towns of Italy (Florence-based, now all over Italy), and I can’t recommend them enough.

Rose of the Trip:

Unexpectedly witnessing the procession of the Scoppio del Caro into the city, pulled by four enormous white Tuscan cows on Easter morning, proceeded by flag throwers, drummers, and representatives of the Florentine Guilds in historic dress. Also, helping my sister select her Florentine ceramic dishware in celebration of her 30th wedding anniversary - they’re spectacular.

Thorn of the Trip:

Only getting one full day in the countryside! Next time, I’m exploring more outside the city (thank you, Florence’s ultra-connected train station).

Bud of the Trip:

THE ART. Florence is the birthplace of the Renaissance and overflows with artwork, so much so that it’s hard to know where to start. Obviously, The David and the Uffizi Galleries. But there is soooooooo much more to see and experience. I am really looking forward to soaking up much more when I return.

Where to Eat (& Drink) in Florence

We ate our way around Florence. I’m still in a food coma. Here are our favorites:

1. Cibrèo Caffè

2. La Giostra

3. Buca Lapi*

4. Osteria Vini e Vecchi Sapori

5. Irene Firenze

Our most memorable meal was at Buca Lapi, not because of the delicious food (we enjoyed every spring special offered), but because of its 80-year-old owner, Luciano. Luciano welcomed us like old friends, made sure everything was to our liking, and sat with us and shared his story. We were one of the first tables seated, and one of the last to leave. At the end of the evening, Luciano sent us home with a bottle of wine and wouldn’t let us pay for our meal - it was “his gift” for my sister’s birthday. It was a night we will hold close for a long time.

We also checked out a few rooftop bars:

1. Loggia Roof Bar

2. 701 Rooftop Bar*

3. Cosimo

I could have stayed cozied up at the 701 Rooftop Bar drinking their smoky Negronis all night. It felt like we could almost reach out and touch the Duomo. We were so close!

Weather/Packing Tips for Spring in Northern Italy

I wish I had packed a lightweight puffy jacket! Other than that, I packed well. What was hard was how the weather shifted daily. We mostly experienced sunshine and blue skies, but did have a couple of windy, brisk days, and one day of rain. I tried the Sudoku Packing Method for the first time on this trip, and almost managed to fit everything into a carry-on! I really wanted to bring my cowgirl boots, which I’m glad I did, but they bumped me up to a checked bag. The Sudoku Packing Method is a capsule wardrobe approach for travel that involves selecting 9 core items - three tops, 3 bottoms, 3 layers - arranged in a 3x3 grid to create up to 27 outfit combinations. It also allows for 3 pairs of shoes, one handbag, one belt, and jewelry. If it hadn’t been so windy and chilly a couple of days, I would have worn everything I brought.

Grazie, Sister.

The moral of this story? Sometimes you need to step away from the everyday, share new horizons with someone you love, and say YES to trying something new. Be it a language program, a Vespa ride through Chianti, or a roof-top smoky Negroni.

If you have questions or want to chat Italy—or travel dreams in general—let me know. And if you need packing tips, itinerary recs, or want the story behind any photo from the trip, I’m always happy to share.

xo,
Sheryl

First of all, thank you so much for your sweet notes after my announcement about my new career pivot as a professional travel planner with Fora. I’m thrilled to share that I’ve already planned over 50 trips! Your support and curiosity mean the world to me as I embark on this next chapter.

Right now, I’m actually writing you from the heart of Italy, where I’m traveling with my sister. We’re in Florence for the week and planning to scout out a long-term home for my own “study abroad” this winter. I’ll be spending two months in Florence starting in December, and I wanted to find just the right spot. We’ve booked a room at a long-term hospitality concept started by a Danish entrepreneur, with locations all across Europe. Depending on how we like it, it may become my home base for the winter—stay tuned.

For my first destination spotlight, I wanted to focus on a bucket-list trip. This one is on my personal list too, so I’ve already done quite a bit of research on it…

Destination Spotlight: African Safaris

A safari is at the top of so many travel wish lists for good reason. Safaris aren’t just for couples or families; I’ve come to realize they are a truly incredible experience for solo female travelers as well. Safaris are remarkably safe, with carefully managed itineraries and guides ensuring you’re taken care of the entire time.

If climbing Mount Kilimanjaro is also on your bucket list, a safari makes for a perfect combination trip. I recommend carving out about three weeks if you want to do both. The weather on the mountain can change daily, so a flexible schedule is key. Another popular option: land in South Africa, spend a few days exploring the stunning wine country, then head off on your safari adventure. Safaris also make for a good multigenerational or skipped-generation trip. Experiencing the magic of the Serengeti with grandparents and grandkids would be so cool.

What Safaris Cost:

I’ve discovered that meaningful and memorable safaris are accessible at a range of budgets, with wonderful experiences possible in the $6-10K range (not including airfare). Of course, a larger budget provides more options—like private pilots to whisk you between far-flung destinations. Whether you’d prefer to stay in a luxe lodge, do a more immersive camping safari, canoe the river to see animals, or do a walking safari (I must admit, walking safaris intrigue me, even if the idea of animals right outside your tent makes me think twice!), there’s an option for everyone.

When To Go:

Both the dry and wet seasons offer unique wildlife viewing. The dry season allows for easier animal spotting as they gather around water, and the landscape is more open, while the wet season is much more lush. Plus, the dramatic wildebeest migration happens at the end of the wet season, which many want to see.

How To Plan A Safari Trip:

I highly recommend planning at least one year, if not two, in advance, given restricted permits and limited space to protect these wondrous ecosystems. I work with three top safari providers—each offering different levels of luxury, immersive experiences, and unique ways to explore from classic truck-based safaris to water-based excursions and camping under the stars.

Some other destinations on my personal bucket list:

• The Galapagos (I’m actually planning to go in December 2027, with a Machu Picchu add-on!)

• Antarctica (Tor penguins, and I would totally do a polar plunge.)

• A walk across England’s newly opened coastal path

• Hiking the Camino

• And a walking African safari

Curious about planning a safari? I’d love to help answer any questions about my research on this. Feel free to book a call with me anytime.

Book A Free Travel Consultation

Arrivederci for now. More stories from Florence soon!

xo,
Sheryl

I’m back.

It’s with much excitement (and a little bit of butterflies) that I’m officially announcing the next chapter for Dare to Detour and the new era for me and my career!

Eight years ago, I created Dare to Detour with a simple goal: to inspire women to embrace transformative travel, to take the Detour when life calls for it, and to gather in beautiful places that offer the space to reflect, dream, and connect. What started as personal explorations grew into unforgettable retreats, deep friendships, and a community of fellow seekers and adventurers.

Over the past few months, since my last announcement, and after countless conversations with women about the travel they crave—and the challenges or hesitations they face—I realized that there was more I wanted to offer. To my friends, their families, their daughters planning their honeymoons, my colleagues, friends of friends…

I want to help you design your own Detours.

So now, I’m thrilled to share that Dare to Detour is officially pivoting: I am now a certified travel planner (and proud Fora Advisor!), offering personalized travel planning services for adventurers like you.

Why the Change?

Over the past year, I’ve noticed just how many of you want to travel in a more purposeful, personal way. But the challenge is time, knowledge, or not having the connections to craft the kind of experience you truly crave. Planning an itinerary can be daunting: Am I missing seeing something essential? Do I have enough time to explore? What if there’s a hidden gem I’d never find online?

As someone who has planned journeys not just for myself, but for friends and friends-of-friends (from Paris to Marrakesh, the Galapagos to Greece), I realized how much I love this process—and how meaningful it is to take the guesswork out of travel for others, so they can simply experience the wonder.

What’s New at Dare to Detour?

A refreshed website! Take a peek at daretodetour.com for all the details about my new offerings:

• Custom travel planning (solo, friends, families, group retreats)

• Sustainable, conservation-focused itineraries

• 1:1 travel consulting calls (for DIY planners who want expert eyes on their itinerary)

• Handpicked recommendations for the places I know and love: Italy, the UK, the American West, and beyond

• And of course, the same honest, heartfelt perspective on travel and life that you’ve come to expect from Dare to Detour

What’s Next?

If you have a trip in mind—whether it’s a solo recharge, a long-overdue friends’ getaway, or a bucket-list group adventure—I’d love to help you make it unforgettable and meaningful.

I hope you explore the new website and share your feedback! Also, keep an eye out for a new rhythm here on Substack: I’ll be sharing a monthly travel trend report, destination spotlights, and advice for those with the wanderlust spirit.

Thank you for being here. Thank you for being part of this journey. Here’s to new adventures, new Detours, and the beautiful unknown roads ahead.

xo,
Sheryl

Eight autumns. That’s how many seasons I’ve had the joy of gathering women at the ranch along the Taylor Fork, watching the aspens catch fire, and feeling that familiar mixture of laughter and tears rise up as we ride into the bright gold at the Nine Quarter Circle Ranch. This year was my last Montana retreat with Dare to Detour, and I couldn’t have asked for a more beautiful and wild goodbye.

From the moment the Darlings arrived, you could feel the hum. Nerves give way to excitement, and this group of strangers becomes wonderfully connected by the end of the week. Mornings started slow and intentional with Nico’s grounding movement and meditations. She was spot on every day, and I loved the way she quietly invited each of us to come home to our bodies before our days under the big Montana sky began.

The horses, as always, were our greatest mirrors. Sydney of Honor Equine guided both large-group sessions and intimate round pen work that was deeply moving. Her closing exercise—a “letter to the horse”—still gives me goosebumps. Prompts like “what I admire most about you is…” and “what I always want to remember is…” asked us to speak honestly to the beings who carried us all week. Simple, powerful, unforgettable.

We rode through color so vivid it felt unreal this year. Galloping into the aspens, I was crying and laughing at the same time. On the final day, wrangler Luke took us off-trail in true Western style, and I just kept thinking, I can’t believe I’ve been lucky enough to do this for eight years. The stars at night were infinite with the clear skies, reminding us how small and infinite we all are.

This final year, I made sure there were many sweet extras woven into the days. Kameron opened the barn with a ranch welcome that set the tone beautifully for the rest of our week. Hilary Honadel led us through screen printing lessons that used embroidery hoops and Mod Podge and turned picnic tables into a creative studio. Many of the women were nervous to try—afraid to “do it wrong.” Here’s why I’ll always champion these practices: there’s so much science showing that art helps us integrate new learning by engaging both sides of the brain. When we’re brave enough to make something, we anchor what we’re discovering about ourselves. It’s not about perfect; it’s about presence.

Bozeman’s infamous Kate and Molly of Fawn & Co. popped up with their upcycled cowboy jeans and vintage wear for the 5th year in a row and brought something extra to the lodge Tuesday night. Showcasing women-owned small businesses from Montana is something I am especially proud of incorporating into every week I’ve Detoured at the ranch.

One afternoon, we snuck away for some fly fishing, and Sara Saxton made magic with her portraits of each Darling in attendance.

There were massages for everyone and plenty of sauna time, compliments of Whitney Truscott and her healing hands. The food? Delicious. And I’ll admit it—I was absolutely jacked on coffee all week thanks to the ranch’s new machine. Happy hours were a ritual. Montana Mules and ranch margs are the Nine Quarter’s signature. (Maybe we can get the recipe?!) And Lindsay Pearl’s music floated across the valley, adding the perfect touch of “vibes.”

For play, we brought back the Ranch Olympics, enthusiastically led by Taylor Lawn. Competing for the Golden Horseshoe brought out our competitive, hilarious sides...complete with bandanas, glitter, and giggles. Several of the women commented on how they couldn’t remember the last time they had actually played like that, which was exactly the point. Mission accomplished! Congrats to Whitney’s team (a.k.a. “Cowgirls Don’t Cry”) on taking home the Golden Horseshoe!

And then there was line dancing. Oh my. Off. The. Hook. Every single woman danced—something I haven’t always seen—and the wranglers were ringers. It got so enthusiastic I joked I’d re-torn my ACL. Whitney even turned her ankle mid–Dirty Dancing leap into Luke’s arms. We laughed until we cried, then danced some more. That kind of collective joy? It’s medicine. The last night was my favorite. Many thanks to Suzi of Western Roots Country Dancing for teaching us all how to line dance with abandon!

Also, one of my favorite surprises was welcoming chainsaw artist Abby Casey. She blew us away and left a carved gift for the Kelleys. It was a beautiful way to say thank you to a family that has opened their home and hearts to us for years.

By our last morning, coffee in hand, I felt the closure I needed. A couple of women were surprised to learn this was the last retreat, and I get it. When something feels this good, we want it to go on forever. But Dare to Detour has always been about listening to the nudge, taking the detour, and trusting what comes next.

Over the years I’ve learned so much about what women in this season of life are seeking: safe ways to travel on their own, experiences that speak to their souls (even if the rest of the family doesn’t share those interests), and the confidence to articulate what we want and need—and to champion those desires in each other. Creating that kind of container has been one of the great privileges of my life.

What’s next for me is a natural evolution. I announced last month that I’m stepping away from hosting Dare retreats so I can focus my energy on giving back in new ways. Two weekends ago, I facilitated my first retreat for the Montana Cancer Support Community—the same community that held me through my own cancer journey. It feels deeply meaningful to use what I’ve learned to support the organizations that have supported me, and to help guide experiences for communities that need it most.

To the wranglers, staff, artists, and practitioners who helped shape this final week: Sorrell, Ried, Luke, Ben, Hanna, Jarrett, Hartley, Taylor, Sydney, Nico, Hilary, Sara, Whitney, Lindsay, Jessie, Suzi, Abby, Molly, Kate, the entire Kelsey Family, and every hand behind the scenes - thank you. To the Darlings who showed up bravely, rode hard, danced harder, and wrote your letters to the horses: you are why I do this.

The trail is wide. The stars are bright. I’m excited for what’s ahead, and I’m endlessly grateful for what we’ve shared.

With love from Bozeman,
Sheryl

I rolled back into Bozeman last night with a full heart and dusty boots. My final retreat at the Nine Quarter Circle Ranch is complete. 🥹 What a week. I’m tender and grateful in all the best ways, and I’m giving myself this weekend to do exactly what my body and spirit are asking for: rest, quiet, and a whole lotta nothin’.

Here’s what you can expect next week: a full recap of the ranch experience, my favorite moments, what surprised me, and some gorgeous photos (Sara came and captured the week so beautifully again). I’ll also share my practical tips for visiting a Montana ranch so you can do one yourself!

For now, it’s a stunning early-fall weekend here, warm days with a hint of crispness in the mornings and evenings. I’ll be posted up on my back patio as much as possible, mug in hand, letting the sun do its good work. September is generous like that. It’s definitely helping me with the permission to slow down.

If you’re savoring the last summer-warm days where you are, here are a few past posts to inspire your own unhurried weekend:

• Favorite Bozeman Hikes https://www.daretodetour.com/detour-diaries/my-favorite-hikes-in-bozeman

• How to Savor Late Summer https://www.daretodetour.com/detour-diaries/how-to-savor-the-late-summer-gap

• How to Embrace Your Tomato Girl Summer https://www.daretodetour.com/detour-diaries/how-to-embrace-your-tomato-girl-summer

• My 2025 Summer Bucket List https://www.daretodetour.com/detour-diaries/my-summer-bucket-list

A tiny weekend practice, if you want one: step outside for three slow breaths, face turned toward the sun. Ask yourself what would feel deliciously simple today—then do just that!

I can’t wait to share the ranch story and all the photos with you next week.

Until then,
Sheryl

I’ve held a lot of circles in my life, but this one felt different. Mending in the Mountains—an annual retreat for Montana women who have experienced cancer—was held September 5–7, 2025, and I was invited to facilitate the entire weekend. It was a profound honor. Cancer Support Community Montana stood beside me through my own breast cancer journey, and to be asked to guide this gathering felt like a full-circle moment of gratitude and purpose.

On Friday, fifty-one women arrived nervous, brave, and carrying the stories that are still very much alive in their bodies. The energy felt fragile, so I changed my plan for how to get started. Instead of big-circle introductions, we began with a grounding practice and a conversation about how grounding supports health and healing. Tears came fast, which I wasn't expecting. It was like the room took a collective exhale. From there, we broke into small groups to meet each other in gentler ways. I offered an anonymous writing prompt: “What’s something you want people to know about you—but would never dare share?” The responses pierced my heart and reminded me why spaces like this matter.

Saturday afternoon, we took on Lone Peak. We took Ramcharger 8 (the biggest high-speed lift in North America) up to the top. For many, the chairlift was scary. Chemo and treatment can make balance unpredictable, hence stepping onto a moving chair demands trust. One step at a time, we did it. All 51 women made it to the summit. At the top, Sue Lynn, a professional flutist, lifted her "inside flute" and played it outside for the first time for all of us - Debussy's music spilling into the sky. It was stunning. The kind of sound that makes you feel stitched back together.

We walked down together. Almost everyone - nearly two-thirds of our group! Two miles and 1,000 feet of elevation. I felt like a mama duck, leading a parade of courage and counting heads, cheering every switchback. Two women took the wrong chair lift, and got "lost in the woods," arriving late to dinner. They ran in flushed and laughing about their misadventure. Joy doing what joy does: sneaking back in through the side door.

On Saturday, I gave my keynote on the Fear/Joy Connection. How fear can be a faithful informant rather than a tyrant, and how joy isn’t frivolous, it’s fuel. Afterward, Jed, our AV lead, told me he recorded the talk so his girlfriend could hear it. “You made me cry—twice,” he said. That felt like confirmation we touched something true. (I'm hoping to get a copy to be able to share with you!)

Before our "farewells" on Sunday, I invited the women to write letters to themselves asking them to:

• Outline 3 ways they will work to integrate what they learned over the weekend into their daily lives

• Identify 1 woman they will stay in touch with and check in on

• List all the ways they will stay anchored in JOY

• Decide where they will play the rainbow prism I gave them as a reminder to seek JOY

• Invite someone at home to be their partner in JOY

The Cancer Support team collected the letters and will mail them to the women in a couple of months as a reminder of our time together, and of their capacity to shift their mindsets away from fear, towards JOY.

We stayed at the Huntley at Big Sky, and I can’t say enough about the care we received. Big Sky underwrote 50% of the food, room, and board—an incredible gift—and the team was thoughtful and gracious. The food was deeply nourishing and beautifully presented, and even amid renovations, everything ran with ease. The lobby buzzed with mountain bikers and older couples, and still, our group felt held. Bravo!

Our circle included women at every stage. Some navigating cancer alongside Lyme disease or autoimmune issues. Each story was different, but what united us was a willingness to show up and be seen.

What I Learned (Again)

1. Brave is plural. Courage multiplies in community.

2. Grounding changes rooms. Breath + body + earth = regulation and relief.

3. Joy is not a reward at the end; it’s a resource along the way.

4. Nature doesn’t fix everything, but it steadies us so we can face what is.

5. Thoughtful logistics are a love language. When meals, rooms, and timing are cared for, people can exhale.

Thank You To Cancer Support Community Montana, thank you for trusting me. To Big Sky and the Huntley team, thank you for your generosity and care. To Jed and the AV crew, thanks for catching the moments we’ll want to remember. And to the 51 women who said yes to a weekend of mountains, music, tears, and laughter - THANK YOU for showing up fully.

This work—partnering with organizations that have supported me, facilitating creative and healing experiences, serving communities that need it most—feels like true north. A reassurance that I'm making the right move to step onto this path moving forward. Appreciation walked with me all weekend. Here’s to mending in the mountains.

xo,
Sheryl

I had grand plans for Labor Day. The kind with packed coolers, my van, and the excitement of a camping trip I'd been dreaming about all summer. Instead, last Wednesday, I woke up, lifted my head from the pillow, and it felt like a hot poker shot through my skull. I couldn’t sit. Standing felt barely possible. Getting out of my pajamas wasn't an option. Anger rolled in, then fear. I left messages for both of my kids; moments later, my son was at the front door. He drove me to the ER. They called it torticollis—stress seizing the neck—more common in babies than a stubborn 60-year-old woman in Bozeman.

I wanted to muscle through it. That’s often been my way. But my body made the call. So I listened. Steroids, PT, neck massage, acupuncture... yes to all the things. I’m facilitating a cancer retreat this weekend for Cancer Support Community Montana, and in two weeks, I’ll be at the ranch for my last Dare Montana retreat. I need my body with me.

I’ll be honest: I got mad. I’ve been working out consistently and feeling strong, and suddenly I’m told not to lift more than two pounds? Two pounds! I want to ride a horse at the ranch in two weeks, smell the leather, feel that sway, let the wind take the static out of my thoughts. And then I heard my own voice, the one I offer other women: slow down enough to hear what’s true right now.

So Labor Day became something else. Dinner with my kids. My son and his girlfriend stayed and asked if I wanted to play dominoes. Dominoes! I’ve never played in my life. Turns out, I love it. Maybe not the game so much as what it created, an evening where presence just was. I went for a drive with a friend instead of our usual hike. We watched the light change on the Bridgers. I stayed close to home, to my body, to my people.

What’s the lesson here? I’m still learning it. But here’s what I know today.

The body whispers until it has to shout.
August was a blur of motion. Good things, meaningful things, but a lot of doing. My neck did not care about my calendar or my intentions. It cared about the cost. This isn’t punishment; it’s information. A fierce kind of kindness.

Support is a strength.
My son at the door within minutes said everything about family and community. I’ve built Dare to Detour on the belief that we’re not meant to go it alone, and sometimes I still need the reminder. Letting people help is a muscle worth training.

Intention over intensity.
My work is shifting. It’s my last Dare retreat at the ranch—this program that has shaped me as much as it’s served others. And it’s my first time facilitating with Cancer Support Community Montana, the organization that held me through my own cancer journey. Those two truths carry weight. No wonder my neck is tight. If the meaning is big, the pace must be grounded. I don’t need to push harder; I need to land deeper.

Grief and gratitude can sit at the same table.
I’m disappointed about the camping trip. And I’m grateful for an unexpected evening with people I love. Both are real.

Detours are teachers.
I say this all the time, and still they surprise me. The road closes, you reroute, and somewhere on that back road, you notice the river you’ve crossed a hundred times but never really seen. These pauses and pivots don’t steal our life; they show us more of it.

If there’s a single lesson in all of this, it’s probably this: choose presence over performance.

And as for the practical, I’m feeling a world better than I did a week ago. Fingers crossed, I'm healing. And about that horse: if my body says yes at the ranch, I’ll ride. If it says not this time, I’ll stand by the fence and breathe in the hay and leather and dust and watch the others. And this weekend, with Cancer Support Community Montana, I’ll walk in humbled and grateful—grateful to give back in a place that held me, humbled by what it means to sit with people navigating fragility and strength at once. It’s a new chapter for my work: partnering with organizations that have supported me, facilitating creative, healing experiences, serving communities that need it most. That feels like a true north I can trust.

Here we are, Labor Day Weekend, a.k.a. the “end” of summer. This week, I could feel the shift toward fall in my bones. And if I’m honest, a swarm of comparison thoughts rolled in too. I caught myself tallying all the big, splashy summer adventures I didn’t have, scrolling past friends who seemed to be everywhere at once — jetsetting in other countries, on camping trips, mountain summits, swimming in lakes. It’s interesting how, right at the edge of a season, the reckoning shows up. Maybe it’s because in Montana, we know what’s coming: long, cold winters that demand preparation and a steady heart.

I brought it to my team, the dread that rides shotgun with inevitable endings, and of course, I’m not alone. So I’ve been practicing a reframe: be where my feet are. Savor the end-of-summer shift instead of grading it. Because I really do love fall oh so much. And there are still many gorgeous, golden weeks ahead before the snow flies. When I actually look back at my own camera roll and calendar, I’ve been out there—often, and with people I love. In the past week, I...

• Went to the Crow Fair and pow wow with my friends Harriet and Steve.

• Wandered KSX Art's makers market with my daughter, then did crucial research: we compared Genuine vs Sweet Peaks ice cream, one kiddie scoop at each. Genuine is the all-around clear winner!

• Snipped my own bouquet at the flower farm at Amaltheia Farms (Four Daughters has a great one too).

• Took my 100th class at Monarch Studio!

• And I’m heading out camping with my kids this weekend.

That’s a full, beautiful life, right here in and around Bozeman. Not performative, not epic, just present. That counts.

I always loved back-to-school as a kid. The new shoes, fresh pencils, a whole new cast of classmates and teachers. As much as I adore pumpkins (and will probably be decorating my porch with those floating pumpkin candles {link} come October), September, for me, is always for “back to school.” It’s for apple picking and watching the first leaves turn, for tightening the laces on our daily rituals and saying yes to what steadies us. I’m letting October be October and letting September be September.

If comparison is nipping at your heels, here’s a gentle practice I’m using:

• Name what you actually did, not what you didn’t. Make a short list. Let it be enough. (Like mine above. It helps!)

• Step outside and find three true things: the temperature on your skin, the color of the sky, the sound closest to you. Be where your feet are.

• Choose one small September ritual. E.g. a neighborhood walk at dusk, a new notebook, a cup of tea on the steps. Keep it simple.

Whatever you did this summer—and whatever you’re doing right now, this weekend—is enough. Truly. Likely, wherever you are is gorgeous in its own way if you open your eyes and take it in.

Here’s to Montana love at summer’s end, and to stepping into September with presence, gratitude, and a little woo hoo. Be where your feet are.

xo,
Sheryl

Reading:

My Life So Far by Jane Fonda. I'm obsessed with her! She wrote the book when she was 60. I highly reccomend this.

Onyx Storm - Started this on my road trip. Obsessed.

Using:

Vibration plate - Following my double mastectomy and resulting disruption of my lymphatic system, it's especially important that I find ways to activate my lymph. A mini tramp and/or vibration plate are really helpful, and honestly, fun. Both make me giggle:)

Marvis Whitening Mint Toothpaste - My Italian toothpaste! I bought this in Italy last year (you can also find it on Amazon), and I swear it’s making a big difference. I’ve gotten a lot of compliments on my teeth and this is it. Even my dentist made a comment!

Getting:

Facials with Lily - I have been going to Nectar Skin for years, but got one before my bday last week and she really is just the best.

Eating at:

Spitz - A new casual dining spot. They just opened a location in Bozeman, and it’s so good! I ordered a bowl with rice and quinoa and immediately split my order to take half home because the portions are huge. They also have wineritas, which are delish.

Three weeks from now (September 15–19th), I’ll be back at Nine Quarter Circle Ranch for our final Dare to Detour retreat at this special place. We’ve been detouring here since 2017, and it has shaped me, our community, and countless women who came as they were and left a little braver. Here are the ten things I love most about the ranch…

1. The road to arrival
   I love meeting you at the Bozeman airport, piling into our passenger vans, and taking the scenic one-hour drive through wide-open country. We always stop at Murdoch’s (a.k.a. Harrods of the Rocky Mountain West) so everyone can snag proper cowgirl boots and a hat. It’s the best icebreaker: laughter, new names, and the first glimmers of sisterhood.

2. The horses
   (And the way they teach us.) Nine Quarter Circle’s horses are bred, born, raised, and trained right on the ranch, and you feel that care in every step. With wranglers guiding us and rides tailored for all levels, you don’t need any riding experience, just a willing heart. These horses hold space for courage, presence, and trust.

3. The Lee Metcalf Wilderness
   Riding into the Lee Metcalf Wilderness is like stepping into a living postcard. Big Sky isn’t just a nickname; it’s a feeling—a spaciousness that helps you breathe deeper and listen more closely to your own story. This is some of the most spectacular country in the Lower 48, and we get to experience it from the saddle.

4. Mornings that ground and fuel us
   We start with movement and rituals to set intention, followed by a hearty ranch breakfast that would make any grandmother proud. That rhythm of body, spirit, nourishment creates a foundation for the day’s adventures.

5. Getting a creative spark
   Each afternoon, we gather for workshops focused on my ongoing theme: Our Stories Matter. Facilitated by other local women who inspire me, these sessions are invitations to honor your past, celebrate your present, and imagine your future. You’ll leave with practices you can carry into everyday life.

6. Play as medicine
   Last year, the Ranch Olympics were a highlight. Pure, giggly joy. We had a few graceful tumbles in the three-legged race and more belly laughs than I can count. That playful energy perfectly complements the inner work; it reminds us that resilience can be fun.

7. Evenings that restore
   There’s minimal tech at the ranch, and the stillness is real. Everyone sleeps deeply out here. It’s something about the quiet, the fresh air, and the way the day uses you up in the best way.

8. Great food — and “Ranch Margaritas”
   The ranch kitchen turns out delicious, satisfying meals, and they’ve consistently met our group’s dietary needs without a hitch. Sitting down to eat together is one of my favorite parts of conversation. And the Ranch Margaritas at Happy Hour? I’ll just say… IYKYK.

9. Saying yes to learning new skills
   From line dancing to cold plunging in the river to trying your hand at fly fishing, I’ve said yes to so many new experiences that remind us how capable and alive we are.

10. The people
    The Kelsey family has stewarded this working horse ranch for over 75 year, and is now under third-generation management. Their pride and hospitality are woven into every detail. Add the wranglers, the Dare Crew, and the women who show up ready to be real, and you have a community that feels like home. This place has held so many of our Detours since 2017. Ending our chapter here feels both tender and right.

P.S. We have three spots left for September 15–19 at Nine Quarter Circle Ranch. If your gut is nudging you, listen. Come as you are. Let the horses, the sky, and this community remind you who you’ve always been and who you’re becoming.

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I've come to understand each Saturn return as a threshold. It's a transition from one phase of life into the next: from youth to adulthood. Adulthood to late middle age. Middle age to eldership. They are wake-up calls that ask us to consider our aspirations and readjust our aims for the next phase of life.

I turned 60 last Thursday under a big, benevolent Montana sky—and with that, I closed out my second Saturn return. I can feel the arc of it, the gravity, and the grit. For me, the unraveling began around 55, and the deepest excavation happened from 57 to now: I completed the dissolution of my marriage, I stopped cancer treatments, I faced down more endings than I thought I could hold. Also, I took the Saturn return course in the Chani app somewhere in there, and it gave language to what my bones already knew: Saturn returns don't punish, they teach. They are thresholds, transitions from one phase of life into the next: from youth to adulthood. Adulthood to late middle age. Middle age to eldership. They are wake-up calls that ask us to consider our aspirations and readjust our aims for the next phase of life.

Maybe that’s why I feel called—responsible, even—at sixty to turn and offer a hand to those of you in your 20s, heading into your first Saturn return. Wobbly doesn’t mean wrong. Hard doesn’t mean hopeless. Sometimes the Detour is the only road that gets you home. But perhaps your version of it can be a little less bumpy with some shared stories of what it's felt like to normalize your experience. If you (or your daughters) want to chat about this, I'm very into it lately!

Also, what’s wild and wonderful is that three generations of women in my family are in Saturn seasons right now. As I complete my second, my daughter is starting her first at 27. My mom is beginning her third at 86. My sister is stepping into her second and is what I like to call “astro curious.” We’re a living constellation. Different orbits, but the same sky.

This week, sixty showed up with celebration and ease. My dear friends Lily and Harriet threw me a little backyard shindig. All I had to do was put on a dress and show up—what a joy to be cared for like that. Harriet's daughter Ivy put together a playlist of songs from some of my favorite movies: The Big Chill (that soundtrack still slaps), The Sound of Music (Oscar winner the year I was born), A River Runs Through It, and Legends of the Fall. Clearly, I'm a sucker for Montana stories, harmonies, and a good ensemble cast. The guest list was intentionally small and multigenerational - my preference always. Highlights of the evening: rolling down a grassy knoll in the backyard hand-in-hand with a friend's 7-year-old son, shotgunning a beer (check that off my 59 for 59 list), and cherry pie!

But here’s the truth about turning sixty: I don’t ever want to repeat my 50s. That decade undid me. And it rebuilt me. Both can be true. Now, stepping into my 60s, I feel a full-body woo hoo (!!). Bring it on.

My north star for this decade is that I’m going to decide where I want to live for the rest of my life and move there by the time I'm 75. I don’t want my kids worrying about it, and I’m wide open to a communal living situation with girlfriends—shared porches, shared meals, shared sunrise walks. Sovereign and held. That’s the dream I'm hoping for myself.

And because I’m me, I’ve also set a few Dares for my 60th year. Here they are:

1. 1. I'm going alpine skiing for the first time since the boobs. years ago, a physician looked at my DEXA scan and told me my back might break if someone crashed into me. That lodged in my head and held me back. I’ve worked hard to rebuild my bone density and my courage, and I’m ready to click in again.

2. My big trip in 2026 will be a pilgrimage. (I'm seriously looking the El Camino in Portugal. Has anyone been?!)

3. I'm getting a tattoo: "Sine Metu Vivere" in my own handwriting. It means Live without fear. On skin, in spirit.

I believe in the power of Detours to shift perspective and build resilience. I’ve seen it in my life again and again—from Oregon forests to New York City sidewalks to California beaches to Montana mountains. If you’re feeling the tug to take one, consider this your permission slip. And if you want community while you do it, that’s why I built Dare to Detour. To gather women who are ready to rediscover themselves, together.

Here’s to the next decade of Daring and devotion. To bees and backcountry, porch lights and pilgrimages, friendship and fresh tracks. To living without fear... or at least with fear in the passenger seat while I drive.

Sixty, I’m ready. Woo hoo.

xo,
Sheryl

P.S. On the adventure front, thank you for all the love on my 21-day van recap. So many of you said it inspired you to try your own version. Even my mommy commented on my posts. (Very Daring of her!) I’m planning a quick camping run to the Boulder River Valley to keep the momentum going (and to finally figure out my compostable toilet… apparently, kitty litter is the secret no one tells you about!). I'll also be out there catching bumblebees for the Montana Bumble Bee Atlas. Netted bees, wide rivers, quiet nights. Sounds like the best kind of homework.

So this month, McCall has been so gracious to pull back the curtain on her family’s most beloved French escapes for us. Whether you dream of sipping a chocolat chaud in Paris, wandering through endless fields of purple in Provence, or simply letting go of your “must-see-everything” energy to embrace the art of doing less, McCall’s France with Bebes: A Provence Travel Guide is the inspiration you need. McCall’s approach—gentle, present, delightfully delicious—reminds us how travel can nourish every season of life, especially when toddlers are in tow.

In this month’s guide, you’ll find:

• A two-day Paris stopover (perfectly doable with little ones)

• The best places to play, eat, and unwind in Provence

• Savvy travel tips for stress-free international travel

• A packing list and Google Map treasure trove with McCall’s links to all of her favorite places in Paris & Provence

• McCall’s French-girl shopping list

• A curated French vacation Spotify playlist to daydream with

• And more… (including McCall joining me on our live Coffee Chat Aug 20th!)

GET THE GUIDE

McCall lives by this Anthony Bourdain quote, which she says sums up how she feels about all of France:

"Most of us are lucky to see Paris once in a lifetime. Make the most of it by doing as little as possible. Walk a little, get lost a bit, eat, catch a breakfast buzz, have a nap...eat again. Lounge around drinking coffee. Maybe read a book. Drink some wine, walk around a bit more, eat, repeat. See? It's easy."

Tell me. Is Provence on your bucket list? Have you been to Paris? Let me know your thoughts on this city/any tips you would add for the Darlings who are planning to go!

There’s a magic that flickers at the beginning of every Detour. A hesitation that finally tips into “yes.” This past month, I got reacquainted with that feeling over4 21 days on the road — Montana, Oregon, Washington, British Columbia, and Alberta— my van carrying me to visit family, familiar faces, wide rivers, gorgeous campsites, and surprising peace.

This was the longest I’ve ever been away—ever. Not even on honeymoon, for work, for anything have I been away from my home for over 3 weeks. And as I pulled back into my driveway in Bozeman, I couldn’t help but ask myself: “What in the world was I waiting for?”

Learning My Van

One of the things I appreciated the most from this trip was getting to really know my van, Gypsy Rose. How she corners on winding highways, where the light creeps in just before dawn, how much space I need (and don’t need) to feel comfortable. This trip was my first real “test run” of being fully out on my own, off-grid for much of it, for nearly three weeks.

I didn’t anticipate how much my little home on wheels would open the doors to connection while also supporting my independence. My friend Yvonne tagged along for most of the Canada stretch, and it was so easy—intimacy when we wanted it, space when we needed it. The same was true when I stopped in Whitefish on a lark, staying with my dear friend Sydney. With the van, I could slip in and out: present, but not imposing. I felt grateful for the flexibility and for people who invite me into their lives with such warmth.

My morning coffee hits different on the road, and having a full coffee setup is something I was super happy with. By full coffee setup, I mean easy access to my moka pot, coffee beans ground perfectly, filtered water, and half + half. My stove top runs on camp stove propane, so having a backup tank was the key for my morning peace of mind. And I was so glad I took the time to fully understand my water system, which I thoroughly cleaned and filled with filtered water before I left. Having access to clean water in the safety and privacy of my van in the early mornings and before going to sleep was huge, especially while I was traveling solo.

Oregon, Washington, & Montana: Family, Friends, and Everything In Between

One of the gifts of slowing down is having time to really see people. Where they’re at in their life, all the small victories and daily struggles. I found myself deeply grateful for evenings around a campfire, walks along rocky shores, and rambling conversations with the friends and family I visited. I kept thinking about how these connections tie in to Dare to Detour—the ways we can reimagine community as something layered and fluid, always there, but never trapping.

I had a lot of windshield time on my road trip, which granted a lot of self-reflection. Turning 60 is hitting me. I want to really be intentional about what I spend my time and energy on in the next decade in my life, so I came to a big epiphany on this trip and announced last week that Montana will be my last retreat for a while. Sometimes, Detours show you not just where you want to go, but what you’re ready to lay lovingly down.

Canadian Kindness & Seriously Clean Campsites

Out of everything, the Canadian campgrounds were a revelation. Outside of Kamloops, I rolled into the cleanest campsite I’ve ever seen—perfectly raked, not a scrap on the ground, firewood ready, and axes supplied. Not one thing was handed to me in plastic. It’s funny, the things that stay with you.

And safety? I never felt off, not even once. The other campers were present but not overbearing. Rolling into Jasper, I was so impressed by the recovery there so soon after the devastating fire. Whole campgrounds, once blackened, are now thoughtfully redesigned and thriving.

Public lands felt like public treasure. Parks in Jasper and Banff were free, and every gesture, down to tourist discounts for the summer of 2025 and encouragements to use local firewood, felt like a nudge from the universe: Come see beauty, and while you’re here, rekindle your own spark, too.

Banff: Fashion, Teenagers, and Great People-Watching

Banff gave me the best people-watching I’ve had in ages. International travelers in every shade and style, teenagers dressed as animals (because of course, why not?), selfie sticks held at every angle, keychains jingling from bags. This was definitely the most touristy section of my road trip, but I loved it!

Pro tip: Order the Tagliatelle Bolognese pasta at Pizzeria Sophia in Banff. It was one of the best Italian meals I've had in a long time.

What I Learned, What I’ll Carry Forward

Highlights:

• Time to myself, to think, to slow down.

• Canada’s wild, immaculate campgrounds.

• Camp-girl dinners

• Connecting with family and close friends

• My Trelino composting toilet, seriously

• Jane Fonda's autobiography "My Life So Far" on Audible

Lowlights:

• The occasional lonely patch, when the road stretched on or the rain wouldn’t let up.

• Logistics—border crossings, restocking supplies in out-of-the-way places, and figuring out how to pump gas at the Canadian gas stations.

• I wish I had brought my bike with me!

What to Be Prepared For:

• I decided to bring my Yeti cooler and thank goodness I did. My fridge stop working the last few days of my trip

• Trust your gut. When a campground or a stop feels right, follow the nudge. When it doesn’t, keep moving.

• Know how your gear works, and where you can find support along the way if needed.

• Make sure you have actual maps and atlases as a backup for GPS/Google Maps.

My Epiphany: I Need More of This

If you hear nothing else, let it be this: What are we all waiting for? Twenty-one days in my van invited me back to myself. I need more of this—not less. There’s life out there, full of Detours, and every bend in the road is an invitation to remember: you are bravest when you listen to what you need, even if it leads somewhere you’ve never been before.

Here’s to what’s next, to gathering wandering women and wild hope, and to always saying yes to the road ahead.

xo,
Sheryl

Who is Dare Guides really for?

This membership is perfect for those who love to explore, dream about travel, or just want to simplify trip planning without sacrificing authenticity. Whether you're a seasoned traveler who's tired of the same old "top 5 must-sees" lists, or you're just starting to venture out and want guidance you can trust, the Dare Guides are here to inspire and support your journey.

I created this for women like you—women who crave real experiences over Instagram moments, who want to feel like locals rather than tourists, and who understand that the best adventures often happen when you step away from the crowds. If you've ever found yourself overwhelmed by generic travel advice or intimidated by solo travel planning, this community is your safe haven.

What exactly do you get with the membership?

Your Dare Guides membership is like having a well-traveled girlfriend who's done all the research for you! Here's what's included:

• Off-the-Beaten Path Itineraries Around the World – Every month, you'll receive expertly crafted travel guides for beautiful destinations that go far beyond the typical tourist traps. These aren't just lists of places; they're thoughtfully curated experiences designed specifically for female travelers.

• Monthly Community Coffee Chats – This is where the magic really happens! Join me live each month for intimate 30-minute conversations where we dive deep into destinations, share travel stories, and you can ask all your burning questions. Can't make it live? No worries—recordings are always available.

• Budgeting Tools for Travel – Let's be honest, money shouldn't be the barrier to your dreams. I've partnered with my personal financial planner, Harriet Chase from Aspen Grove Wealth Management, to create resources that help you save smartly for your adventures.

• Product Recommendations Specifically for Women – From the perfect travel underwear to the books that will transform your journey, I share my most trusted recommendations with complete transparency.

• Bonus for Annual Members – Choose the yearly option and you'll get a complimentary 45-minute one-on-one consultation call with me! We can dive into personalized trip planning or even chat about entrepreneurship questions if that's calling to you.

How often are new guides released?

One brand new guide every single month! I know how exciting it is to have fresh inspiration regularly, so you can count on discovering a new destination on the same date each month. Whether it's the rugged beauty of Scotland's North Coast 500 or the vibrant souks of Marrakech, there's always a new adventure waiting for you.

What does the membership cost?

Here's what I love about this: for just $7 a month—literally the cost of your favorite latte—you get access to everything I mentioned above. If you're ready to commit to a year of adventures, you can pay $77 annually and save some money in the process.

I chose this price intentionally because I believe transformative travel shouldn't be a luxury reserved for the wealthy. This is about making expertly curated travel guidance accessible to women who are ready to prioritize their own adventures.

What if you're not planning to travel to the featured destinations?

This question makes me smile because it shows you're thinking practically, and I appreciate that! Even if Morocco or the Dolomites aren't on your immediate radar, there's tremendous value in being part of this community.

You'll gain access to discounts with our partner brands, those monthly coffee chats where we discuss travel strategies that apply anywhere, and my curated recommendations for books, gear, and resources that will enhance any journey you take. Plus, you'll be connected with other adventurous women who might just inspire your next unexpected detour!

When are the Coffee Chats?

I host them once a month, typically toward the end of the month at 10:30 AM Mountain Standard Time. I chose this time because it works well for most of us across different time zones, and there's something magical about mid-morning conversations when our minds are clear and our coffee cups are full.

Will you actually meet other members?

Absolutely! The monthly virtual coffee chats are where our community comes alive. You'll meet fellow Daring Darlings from all walks of life who share your passion for authentic travel. And here's something exciting—members get early access and exclusive savings on Dare to Detour retreats, so there might be opportunities to connect in person at future adventures too.

The connections formed in this community go far beyond travel tips. We're creating a network of women supporting women, sharing not just destination advice but life wisdom, courage, and inspiration.

Don't Miss Next Week's Special Coffee Chat!

Speaking of our monthly coffee chats, I have something incredibly exciting to share with you! I'm just returning from my 21-day solo road trip, and I can't wait to spill all the details with our Dare Guides community next week.

For our members, I've already shared my complete 21-day road trip itinerary with all the insider details you need to recreate this journey yourself—it's this month's featured Dare Guide! This week, I'll be hosting a live Zoom Coffee Chat, where I’ll answer your questions about my time on the road and how to recreate your own adventure.

If you join the Dare Guides community now, you'll have immediate access to the full road trip itinerary and can join us live for this special behind-the-scenes conversation. It's going to be raw, real, and full of the kind of practical wisdom that only comes from actually living the adventure.

Join the Dare Guides

Ready to join the adventure?

If you've read this far, I have a feeling your heart is already saying yes. Trust that instinct! The world is vast and beautiful, and there are so many incredible experiences waiting for you. Let's explore them together, with the confidence that comes from expert guidance and the joy that comes from authentic community. I hope you check out these special guides. I put my heart into them each month!

xo,
Sheryl

Hi Darlings,

I’m writing to you from a propped-up, sun-warmed chair in the heart of Washington Wine Country. I’m deep into my great 60th birthday road trip adventure—a little sun-kissed, a little margarita-fueled, and a lot reflective. I’ve had a lot of windshield time with my thoughts. There’s something about a long drive that helps me peel back the noisy layers and get my head clear.

Last week, I gathered with my family and my New-Old friends to celebrate milestones - my sister’s 29th and my parent’s 62nd wedding anniversaries, and my 60th birthday - south of Bend, Oregon in Sunriver. There were handmade bud vases and napkin rings made by Kirly (who, by the way, found her love of clay at a Dare retreat and is now headed to Italy for a ten-day immersion—proof in action that learning never stops, and you never know what door a Detour might open!). There were hand-calligraphed place cards made by my friend Yvonne, flowers by my friend Kristin, and laughter and love from all who gathered.

During dinner, my nephew’s girlfried, fresh into her twenties, asked me a tender question: “What advice would you give someone my age?” On the spot, I answered:

1. If you can stay true to yourself and know what your core values are, everything always works out. When I look back, even at the hardest moments—divorce included—trusting my gut was my lifeline.

2. Choose your partner with eyes wide open. And live with them first! We see red flags, but oh, how often we ignore them. How we are together in daily life tells you so much more than words or big gestures ever could.

On my drive the following day, my tires rolled north toward Sunriver, that question kept echoing in my thoughts. What would I add, now, to my answer? What has the benefit of *almost* 60 years, a half-dozen pivots, and my fair share of heartbreaks given me perspective on? What do we owe our 20-something selves?

Here’s what crystallized:

You will be asked, quietly and constantly, to put others first. As women especially, we often find ourselves automatically taking on the role of caregiver—the one holding it all together. So much of it is unspoken, but those roles can become concrete before we even realize what’s happening. In my own marriage, my path as primary caretaker wasn’t so much chosen as it just...unfolded. Babies, illnesses, life. Suddenly, what felt like “just helping” became a full-time job that I hadn’t consciously agreed to. Looking back, I wish my husband and I had had more honest, regular conversations about what we both wanted, what we both needed.

If you bury your needs, they grow underground. There’s an old truth: “What you bury grows.” If you don’t say the hard things, if you keep shoving yourself to the bottom of the list, those feelings don’t disappear—they wait. I learned, sometimes the hard way, that writing your concerns down, naming them kindly but clearly, can be magic. It creates air, a way forward, and the chance to be seen.

So, to the beautiful twenty-somethings (and to anyone, really):

• Get fluent in your own values.

• Learn what you’re truly hungry for, outside of anyone else’s expectations.

• Keep asking yourself and your loved ones the hard questions, early and often.

• Community, creativity, and courage are always worth cultivating.

And above all: Don’t fear the Detours. In my experience, this is where you find out what you’re made of. And where you discover the wild, surprising corners of your own heart.

Now, I turn the question back to you, my wonderful community: What advice would YOU give a 20-something-year-old? What do you wish you’d known sooner, or Dared to do without apology?

With all my love from the winding road,
Sheryl

P.S. If you haven’t watched “Women Holding Things” by Maira Kalman (shared by Maria Shriver HERE), please take a few moments. It’s a balm and a revolution in poem form. You’ll see what I mean. 💛