Transformative Experiences
About Dare to Detour®
Dare to Detour® was born from the belief that the best moments in life (and in travel) often lie just beyond the planned route. Here, you’ll find personalized planning that focuses on local immersion and intentional itineraries and gives you enough space to pause, embrace the unexpected, and connect deeply—with places, with others, and with yourself on your trip.
Meet Sheryl
I believe every journey can be transformative. Especially when you let the Detours surprise you.
Based in Bozeman, Montana, I’m the heart behind Dare to Detour. Through decades, detours, and destinations, I’ve helped hundreds of women and families use travel to shift their perspective, rediscover joy, cultivate resilience, and reconnect with themselves and each other.
From mapping multi-generational trips through Italy’s countryside to leading intimate retreats in the wilds of Montana (often helping first-time solo travelers along the way), my practical expertise and passion for finding hidden gems inspire the itineraries I create. With Fora Travel, I offer access to a global network of insider perks, hotel and travel rates, and advocacy and support should your plans need to pivot.
Whether you crave travel with your family, a solo escape, or inspiration for your friend group’s next big adventure, I bring a blend of practical organization, real-world wisdom, and a genuine love for the little details that make travel feel effortless and extraordinary.
I want you to feel not just prepared, but empowered to experience the world in a way that lights you up.
I am also a gal who:
Has guided 200+ women on Detours in Montana and beyond
Loves to solo travel in her van
Worked on Wall Street back in the day
Is currently studying to become a Master Naturalist
Survived breast cancer
Is a proud mom to two amazing young adult kids
Always wished she had studied internationally, so is planning her "semester abroad" in Italy for the end of 2026
Is standing strong after divorce
Finds that learning and trying new things light her up
A Little Dare to Detour History…
Founded in 2017, Dare to Detour began as a series of empowering women’s retreats designed to encourage resilience, connection, and transformation through shared adventure. Over time, it evolved to focus on personalized travel planning, allowing even more people to experience the joy and growth found in life’s unexpected journeys. Today, I continue to help clients embrace meaningful detours worldwide as a Fora Travel advisor.
My own journey of detours
01.
Moved Cross Country
Dared my 20-year-old self to move from Oregon to New York City where I lived and worked for 11 years (1987 - 1997)
02.
Chose Motherhood
The most challenging and rewarding experience of my life (1997 - present)
03.
Beat Breast Cancer
Two surgeries, treatment and just over six years later I am happy, healthy and cancer free (2019 - present)
04.
Decided on Divorce
Made the difficult, profoundly sad decision to leave my 32 year relationship (2020-2024)
05.
Pivoted in Business
After guiding 200+ women on Detours worldwide, I became a trusted travel advisor affiliated with Fora Travel to fulfill my passion for connecting more people and places (2025 - present)
Living the Detour:
From My Story to Yours
Every chapter of my life has taught me that Detours lead to the richest discoveries. These pivotal experiences inspire how I design every itinerary for my clients, creating travels that prioritize resilience, discovery, and that embrace a spirit of meaningful adventure.
How I Choose to Detour
Meet Gypsy Rose, My “Freedom Van”
In the spirit of the new chapter I find myself in, I bought a camper van! Check out my experiences detouring solo:
A Guide to Solo Road Trips
My First Solo Road Trip
Why Every Woman Should Experience Solo Travel
Our Stories Matter
Playlist
This playlist features songs that I have repeatedly turned to as I've moved through the past few years. Some I dance to, some I sing along with, some make me smile, some make me cry, and some I simply hold in my heart. So Darling, download "Our Stories Matter", turn it up, and DANCE!
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.