Travel club. Wellness retreats. An escape from the noise.
Whatever you want to call it, our retreats gather Reckless Optimists from all over the world in one destination to harness the power of collective energy, immerse ourselves in new cultures and perspectives, and seek JOY outside of our day-to-day lives.
2024 RETREATS COMING SOON. Get on our mailing list to be the first to know about our trips.
ZION 2021
SEDONA 2021
PATAGONIA 2023
A WORD FROM OUR RECKLESS OPTIMISTS
“I don’t know what I expected from Reckless Optimist when I booked the trip, but it far exceeded anything I could have ever imagined. From the incredible trip guide (Hope!!!), to the rustic swanky glamping, to the unstoppable energy that is Jessi Duley, and to the 14 women I had never met but immediately loved, it was by far one of the most memorable and soul changing experiences I’ve ever had. I couldn’t recommend pushing yourself and diving into an R/O trip more!”
— TORI C
I”t took a bit of courage to commit to a last-minute spot on a retreat with no one I knew, but the experience with Jessi, Kelsey, and the OG R/O crew will forever be sacred in my memory. Our time together was scary, liberating, funny, touching, and informative. The accommodations and meals were unique and wonderful, and the programming struck the perfect balance of structured time and free time to relax and get to know one another. I hope to make a R/O retreat an annual experience for myself.”
— VERONICA M
"What can I say about Reckless Optimist and this incredible gift I was given. For someone who does well in a crowd but prefers isolation, this trip gave me tranquility, purpose, a voice, a friendship with so many beautiful humans it's almost impossible to express the gratitude. I was taken out of my comfort zone and led hand in hand through hikes, workouts, heavy-handed margarita pours, hugs, openness, cultivating a bond and so much more. I would follow these humans anywhere and I'm baffled to say that out loud after only 3 days together. Thank you for the experience Reckless Optimist. My heart is open and full and ready for more.”
— DINA W
“I signed up for Zion not knowing what to expect and walked away with an experience I never knew I needed. This trip was curated perfectly and it was such a relief to not worry about anything but showing up. There was so much time and space for connection with self and others with that special Jessi Duley touch: luxurious and beautiful accommodations, vision and journaling workshops, epic workouts, silent disco dance parties, fireside chats, canyoneering adventures, private group cocktail hours and dinners, and the space to just BE...this trip had it all! I didn’t want to leave but I was so excited to bring back memories and friendships that I will never forget. It was my first retreat and I can’t WAIT for more!”
— MALLORIE H
“I highly recommend any Reckless Optimists retreat for anyone looking for deep connection, self-care, and a taste of adventure! Jessi and Kelsey do an amazing job curating a meaningful agenda, they attract impeccable humans and do everything possible to make your time well-spent. I cannot say enough how transformative the experience is for anyone looking to step out of the formidable comfort zone. Go ahead, commit, make the time, you won't regret it.”