Dare to Detourยฎ
Transform how you travel.
Rediscover wonder. Travel deeper, not just farther.
An affiliate of
Current Popular
Destinations
Foraโs 2026 Hot List Locations:
Mexico City
Lesser-known Japan
The Nordics
South American Beaches
The Carolinas
Galรกpagos Expeditions
Sail the iconic archipelago with the pioneers of modern expedition cruising
Meet Sheryl
Your Expert Travel Planner and Detour Advocate
Iโm Sheryl, based in Bozeman, Montana, and Iโm the heart behind Dare to Detour. I bring over 20 years of travel-planning experience to my work and have helped hundreds of women and families rediscover resilience, joy, and connection through travel. From crafting multi-generational journeys across Italy and Scotland to organizing seamless solo van trips, leading group retreats in Montana and abroad, and supporting dozens of first-time travelers, Iโve learned that thoughtful planning is the key to unlocking lifeโs richest travel moments.
Where Will Your Detour Take You?
I specialize in seamless, meaningful travel for:
โ Solo travelers
โ Multi-generational families
โ Retreats & small groups
โ Road trips (van or car, letโs dream BIG!)
โ Honeymoons & babymoons
โ Custom journeys tailored just for you
Destinations I Know and Love:
Italy
United States
Portugal
France
Greece
Scotland
Peru
Morocco
Expect more than just logistics: I plan hotels, flights, car transfers, immersive activities, and all the details so you can truly be present and enjoy the journey.
The Process
โ CONNECT
Fill out my quick inquiry form, and weโll hop on a call (or meet for coffee if youโre local to Bozeman) to dream up your ideal trip and talk budget.
โ DESIGN
I send you a custom proposal. Once you love it, I handle bookings, itineraries, and all those โwhat-ifโ details (so you donโt have to).
โ GO & GROW
You travel, fully supported! Iโm just a message away for help or advice while youโre out in the world.
Expertly Crafted, Unhurried Adventures: Plan a Detour in 2026
Why Dare to Detour?
Sustainability
Traveling with respect for local people and places, supporting small businesses, and sustainable pacing (so you return restored, not exhausted).
Empowerment
Every woman deserves transformational travel โ solo, with friends, or with family.
Support & Advocacy
Youโll have my guidance every step of the way, plus access to VIP perks through Fora (room upgrades, spa credits, and more).
Deep Immersion
Ditch the โTop 5โ checklist and embrace a few Detours. Savor gelato in a hidden village or lose track of time in a conversation with a local at a foreign cafe.
Free Resources
The Dare Guides
Want to skip the tourist traps and dive into the true heart of a destination? These thoughtfully curated, โlike a localโ itineraries are packed with hidden gems, favorite restaurants, unique stays, packing lists, and honest recommendations.
Sign up with your email and gain access to a new Dare Guide each quarter.
Other ways to Detour
DIY Detour
My 8-week guide to get off the beaten path โโโ in your hometown or anywhere.
Detour Diaries
Stories of resilience, solo travel, budgeting tips, and more.
Join the Dare Email List
Stay inspired and informed about the latest travel trends without getting inundated. (Just about two emails a month.) Enjoy a monthly travel report, spotlights on destinations Sheryl loves and recommends, practical travel tips, and thoughtful personal perspectives on travel and lifestyle.
