Past Detours
As a community of Darlings, we are focused on unlocking our potential by Daring together and exploring new places.
What Past Attendees are Saying
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“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!!”
I used to be a last-minute packer. I would ensure my kids were packed days in advance, but I often found myself scrambling to pack for myself well into the midnight hours the night before our departure. But now, my packing routine has evolved into a delightful dance of anticipation and practicality.
When crafting the itineraries for my Dare to Detour retreats, I start by defining what we will NOT do. The point of these trips is that I want it to be a true Detour - not an itinerary you would do with family or your friends. So rather than following the traditional tourist trail or "top 5 must-sees" outlined by popular travel guides, I intentionally opt for truly unique experiences.
I've had countless conversations with women about this. It's a common challenge, but a conversation worth having with your partner to advocate for the transformative power of solo travel. Here are some tips on how to approach the budget convo.
So, you've been tossing around the idea of Detouring with Dare or maybe you're still contemplating. I've heard Mercury is in retrograde, so if you're feeling a bit on the fence, blame it on the cosmos, right? 😊 I'm definitely feeling the need to be extra careful about all of my decisions, big or small. Whether you're ready to take the plunge or still mulling it over, I want to share the truth behind what "all-inclusive" really means at Dare.
Spoiler: it's seriously everything!
I’m in the mood to get real about money, and I want to get into how to master the mental moves that happen behind-the-scenes of big purchases. So, buckle up because I'm whisking you away to the vibrant souks of Marrakesh, where I found myself entangled in a whirlwind of colors, culture, and, of course, rugs!
Italy has this magic that keeps pulling me back – more than any other place. It's like my heart found its favorite spot to dance in the world. I've traveled here more than any other country. I call it my personal Eat, Pray, Love destination. Seriously, it's the nurturing ground for my soul. From our Detour in the Dolomites last year to wandering the streets of Rome all by myself, each trip adds another layer and I’ve come to realize that if you've ever dreamt of traveling to Europe…
Recently, I've found myself reflecting on the essence of travel, the pure joy it brings, and it's got me thinking a lot about treating ourselves to our own adventure.
I LOVE love and my heart has a soft spot for Italy, especially in the fall. This October a group of wonderful Darlings will join me as we immerse ourselves in La Dolce Vita at a 16th-century farmhouse among vineyards and olive groves.
As we step into the New Year, I want to share a personal reflection that has significantly shaped my own journey. We frequently find ourselves in a groove-perhaps a fantastic one-but it often hinders us from seeing beyond our routine. The most impactful approach to break free from this cycle is by embracing change. Want to know the quickest way to make a shift in your life?
Dare to Detour hosted its first-ever Dinner with Darlings event. And it was a truly remarkable evening of connection, shared experiences, and empowerment. The gathering brought together a diverse group of women who showed up fully and embraced the spirit of the event.
Do you like to research in advance and create organized itineraries? Are you the one who handles booking all of the tickets, hotels, rental cars, transfers, and Uber drivers? Do you comb through articles on travel sites for inspiration? Let me guess... are you the go-to planner for your family/friend group/crew?
The thing is, as much as you plan and prepare, you can't know exactly how things are going to roll on the road. Even good road trips have bad days, and unplanned Detours are always a possibility.
Answer: It depends on the things you prioritize as investments in your life. Some people view travel as a luxury item. But for me, it's an essential investment in self. Therefore, investing in travel is important to me.
I’ve been thinking a lot about the adventures I’m still hoping to schedule before Montana’s winter weather hits. And also, I’ve been very reflective about the amazing experiences I’ve had so far this year, some in far-flung places, and what would be additive. It got me thinking…
Sometimes, life throws us unexpected curveballs. Last week, I embarked on a Detour into the breathtaking Beartooth Mountains of southwest Montana. Accompanied by a group of amazing women - my Daring Darlings - this journey turned out to be a deeply personal experience.
My recap of a Montana dude ranch experience.
This was my 6th(!) year bringing a group of Darlings to Detour at the Nine Quarter Circle Ranch in Big Sky... and I decided to put a twist on this one.
This isn't a yoga retreat.
But here’s why we Detour. Detours are laboratories for our hearts and souls. They allow us to step out of our day-to-day, release old stories that no longer serve us, and rediscover who we truly are.
First I will say, Morocco is NOT for the faint of heart.
Even though we broke up our daily activities with rest in the shade and unique experiences in amazing places, the heat and seemingly constant exploration on foot were real - I think we averaged close to 16,000 steps/day?! This being said Morocco was both transformational and incredibly humbling.
Let's face it. Everything gets a little harder to recover from as you get older.
Including jetlag.
At the end of the day, there’s no true cure for jet lag other than time and rest, but here are some of my rituals and tips for long-haul flights that help ease the change into new time zones:
As a 57-year-old woman, I’ve seen a lot of life and a lot of change. But mostly, I’ve come to appreciate the importance of Detours in life. Through them, I’ve encountered many opportunities to grow and evolve. I know that taking risks is often essential to finding true fulfillment, and travel is a great way to do that. So now, I seek them out actively.
Every Detour is a journey of self-discovery and growth.
I find that the best way to maximize the impact of the work I do with the group is to take a solo trip to reflect and integrate my learnings.
A solo female travel experience is incredible for the soul — at any age.
I am deeply passionate about this and believe it to my core. Providing safe and meaningful opportunities for women to experience travel is the intention behind Dare to Detour and it's at the root of our mission.
Do you ever find yourself thinking…?
I want to design the next chapter of my life on my terms. But I'm worried that it's too late to start.
But it will change your life.
Detouring has become my religion.
Why?
Because Detours shift perspective.
You might be wondering why I chose Morocco as a place to travel as a woman.
And why do I think Morocco is such an important place for us to Detour?
Why you can (and should) make a travel budget.
Are budgets your B*&%$ or your BFF? For most of my adult life budgets have been a B*&%$. In 2022 I made the decision to make a major shift, and step by step, I've been turning that B*&%$ into my BFF.
So what have I learned?
These are not the words we typically hear when we come home from a trip…
What is ‘authentic’ travel?
And how do we get more of it?
There’s nothing better than a Detour where you really get a feel for how the locals do it. Whether it’s wandering the cobblestone streets of a small European town or driving down the dusty road toward a mountain ranch, the experiences we all crave are authentic ones.