Past Group Experiences

Group travel requires a different kind of planning — one that balances logistics, pacing, personalities, and presence.

Over the years, Dare to Detour has designed and led intimate group journeys rooted in connection, intention, and care. These experiences reflect a deep understanding of what it takes to hold space for groups while creating meaningful travel moments and they continue to shape how we approach travel planning today.

While Dare to Detour no longer offers retreats as a standalone service, this history of group travel leadership informs the way Sheryl approaches planning today especially for multigenerational trips, group travel, and complex itineraries that benefit from thoughtful pacing and hands-on coordination.

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Words from Past Journeys

Testimonials

“The world would be a better place if all women could participate in a Dare to Detour retreat. Sheryl curates a group of women and an experience we all deserve.”

“I felt held by the women, the mountains, the horses, and the universe. This retreat was life-giving, nurturing and powerful. Every woman needs to experience this type of deep self-love.”

“It was set up in a wonderful way to allow the women who participated time to get to really know each other and the input and participation from the entire crew made it more special. Very well done!”

“My hope for each Daring Darling is that they left the retreat feeling grounded, rejuvenated, and empowered. It appeared that many of Daring Darlings arrived with a foggy mind and a tired soul and body. By the end of the retreat, I could tangibly see and feel the peace and energy radiate from each and every single one of these women.”

“The women Sheryl curated and brought together as a Crew came together unlike any Dare I have been part of previously. There was a magical, unsaid expectation that everyone would show up to support these Darlings to the best of their ability, while also supporting every Crew Member by her side as well. This goes without saying that Sheryl chose every Crew member for a very specific and confident reason. Behind every decision for Dare, Sheryl put so much passion and deep-rooted thought. I can only speak for myself, but it was felt every single day.”

“I have no doubt in my mind that every Daring Darling and Crew Member left this Dare retreat feeling Sheryl's supportive and loving presence.”

"Sheryl has the incredible ability to create a safe, creative and empowering space for women of all ages and backgrounds to show up and come as they are in a vulnerable and authentic way.”

“It was a wonderful weekend. I connected with a great group of women. The activities were thought-provoking and meaningful. And while there were moments of deep introspection, that could be a bit uncomfortable but so important for me, there were plenty of laughs and giggles.”

“Sheryl and her team hit a home run with Dare | Montana. From the time you arrived at the Ranch, you were able to relax and enjoy the great company and conversations with women from all over. I highly recommend it to any woman who needs to reconnect with herself while being lifted up by other amazing women!”

“An invitation from a friend. A community of women. Time to be still, to breathe, to emote. I just spent the most incredible time with Dare to Detour and I could not be more grateful for my renewed, clarified articulation of my own values. I adore every brave, creative human I met and look forward to future connections. Thank you, all! May music, stillness, and light fill us to our core with every step we take.”

“I have been smiling all wknd thinking of how awesome it was to glean so much from our exercises…my husband & I walked for 2 hrs yesterday as I flushed out the day and we both aired so much in such a productive way…I thank you for your prompts! Feeling 100% aligned right now…I was already feeling close but had some nagging feelings that needed to be flushed out and I attribute your work to helping me flush them!!”