The Dare Guides Membership is here.
Meet your guide to off-the-beaten-path travel.
This is an online membership platform, monthly subscription style. For the price of a latte, you’ll get access to thoughtfully vetted, “like a local” travel itineraries for new towns and cities each month. You’ll also have the chance to hop on and chat with Sheryl live each month, ask your travel questions, and get connected to other travel experts and fellow Daring Darlings.
Our Latest Destination
Bozeman & Beyond!
Explore our latest travel guides and hidden-gem itineraries curated just for you! Each guide includes local tips, packing lists, book and playlist recommendations, and more to make every adventure unforgettable.
Plus: A Bonus Bozeman Galentine’s Overnight Itinerary
Join a Supportive Community of Women
Dare to Detour® is a community offering women’s retreats, events, and transformative experiences that empower women to cultivate their creativity, resilience, and vitality.
Upcoming Retreats
Reconnect with yourself — mind, body, and spirit
Know who you are, stand in your strength, and embark on a soul-healing journey into the life that awaits — just past your comfort zone. Dare to Detour retreats support individual growth through shared connection and empowerment.
October, 2026
Walking & Re-wilding
September 15-19, 2025
Giddy Up Cowgirl
October 12-18, 2025
A Food & Wine Exploration
As seen in
Meet Sheryl
Our Founder
“I am Sheryl Wright, the Founder of Dare to Detour®. Drawing from my life experiences and the supportive guidance of experts, I help women find genuine community and connect with who they are now — through retreats, workshops, and transformative experiences.”
Other ways to detour with us
DIY Detour
Free for everyone, everywhere, the DIY Detour dares you to step off the beaten path, experience something new, and embrace your inner soulful adventurer.
Detour Diaries
Dear Darling,
This is my permission slip. I applaud you for giving yourself permission to pause and making an investment in yourself. Now, more than ever, we need to step outside of our day-to-day, out of our comfort zones, so we can recharge and reconnect with ourselves in meaningful ways and continue to lead with strength and love.
