Sheryl Wright
Based in Bozeman, Montana
English
Dare to Detour
Ask us about
Our Story
Exploring back roads, intentionally getting lost, and discovering hidden gems is my jam.
Travel Style
Curating bespoke travel itineraries truly lights me up. I love being able to connect people with places and experiences that shift their perspectives and leave them wanting more. Like a week on horseback in Big Sky country, exploring Rome via scooter, or driving the North Coast 500 in a Defender 110. And if there’s a way to slow down and connect with local makers and artisans, all the better.
Reviews (11)
Amy W.
travel to Florence
2 days ago
Sheryl was instrumental in helping me plan a last-minute trip to Italy. Her recommendations were spot-on and saved me time and money, but most of all provided the most memorable experience! I'm so appreciative of her willingness to talk over my expectations and line up an itinerary that checked all my boxes and was within my budget. Her gentle nudges in the right direction were just what I needed to have the experience that I never could have planned on my own. She was readily available to jump in and help whenever I had questions and followed up with me before, during, and after my vacation. I'm so glad I discovered her service and would recommend her to anyone who wanted to ensure that their vacation was done right the first time without regrets. I can't wait to plan another trip with her.
Lily K.
travel to Santa Barbara
about 1 month ago
We loved working with Sheryl on our last vacation and now can't imagine planning another trip without her. Her extensive travel experience, phenomenal taste, and keen intuition make her outstanding at planning trips that feel like bespoke experiences. She regularly checks to make sure you're getting the best rate even after you've booked, called our hotel ahead of time to confirm we'd be upgraded, and made sure every special request was taken care of. Thank you, Sheryl, for a wonderful trip and for the special attention you gave our family.
Michelle M.
travel to Portugal
about 2 months ago
Sheryl truly went above and beyond in helping us choose the perfect vacation and destination for our family. Her expertise, guidance, and incredible attention to detail made the entire experience seamless and unforgettable. We felt so well taken care of every step of the way and couldn’t have asked for a better travel planning experience.
Michelle G.
travel to Florence
4 months ago
Sheryl is wonderful to work with when planning a trip. She listens carefully to what your dreams and desires are in an adventure and takes the time necessary to cultivate an itinerary that truly exceeds your expectations. She is creative, intelligent, professional, and efficient. I would highly recommend booking your next travel experience with Sheryl!
Luke G.
travel to London
4 months ago
I've used other travel advisors in the past and Sheryl Wright by far has been the best travel advisor! She gave great advise on hotels, sites to see, and new experiences within the city. Her itinerary that she puts together made everything go smoothly. I would reference it constantly throughout my trip. I wouldn't want to book a travel without her. Will definitely be having Sheryl book my trips in the future.
Amy W.
travel to Florence
2 days ago
Sheryl was instrumental in helping me plan a last-minute trip to Italy. Her recommendations were spot-on and saved me time and money, but most of all provided the most memorable experience! I'm so appreciative of her willingness to talk over my expectations and line up an itinerary that checked all my boxes and was within my budget. Her gentle nudges in the right direction were just what I needed to have the experience that I never could have planned on my own. She was readily available to jump in and help whenever I had questions and followed up with me before, during, and after my vacation. I'm so glad I discovered her service and would recommend her to anyone who wanted to ensure that their vacation was done right the first time without regrets. I can't wait to plan another trip with her.
Lily K.
travel to Santa Barbara
about 1 month ago
We loved working with Sheryl on our last vacation and now can't imagine planning another trip without her. Her extensive travel experience, phenomenal taste, and keen intuition make her outstanding at planning trips that feel like bespoke experiences. She regularly checks to make sure you're getting the best rate even after you've booked, called our hotel ahead of time to confirm we'd be upgraded, and made sure every special request was taken care of. Thank you, Sheryl, for a wonderful trip and for the special attention you gave our family.
Michelle M.
travel to Portugal
about 2 months ago
Sheryl truly went above and beyond in helping us choose the perfect vacation and destination for our family. Her expertise, guidance, and incredible attention to detail made the entire experience seamless and unforgettable. We felt so well taken care of every step of the way and couldn’t have asked for a better travel planning experience.
Michelle G.
travel to Florence
4 months ago
Sheryl is wonderful to work with when planning a trip. She listens carefully to what your dreams and desires are in an adventure and takes the time necessary to cultivate an itinerary that truly exceeds your expectations. She is creative, intelligent, professional, and efficient. I would highly recommend booking your next travel experience with Sheryl!
Travel ideas (1)

Montana Dude Ranches for Any Budget
Some of my fondest memories are tied to a dude ranch vacation: watching my kids learn to ride, learning to cut cattle on horseback, supporting women to step out of their comfort zones, and waking to elk bugling on an overnight pack trip. There is something special about time spent at a dude ranch, especially the way you find yourself letting your guard down, relaxing, and truly connecting with yourself and your people. I’ve been going to and hosting travelers at Montana dude ranches for nearly 10 years. For me, they offer the best possible reset.

Montana Dude Ranches for Any Budget
Some of my fondest memories are tied to a dude ranch vacation: watching my kids learn to ride, learning to cut cattle on horseback, supporting women to step out of their comfort zones, and waking to elk bugling on an overnight pack trip. There is something special about time spent at a dude ranch, especially the way you find yourself letting your guard down, relaxing, and truly connecting with yourself and your people. I’ve been going to and hosting travelers at Montana dude ranches for nearly 10 years. For me, they offer the best possible reset.

Montana Dude Ranches for Any Budget
Some of my fondest memories are tied to a dude ranch vacation: watching my kids learn to ride, learning to cut cattle on horseback, supporting women to step out of their comfort zones, and waking to elk bugling on an overnight pack trip. There is something special about time spent at a dude ranch, especially the way you find yourself letting your guard down, relaxing, and truly connecting with yourself and your people. I’ve been going to and hosting travelers at Montana dude ranches for nearly 10 years. For me, they offer the best possible reset.

Montana Dude Ranches for Any Budget
Some of my fondest memories are tied to a dude ranch vacation: watching my kids learn to ride, learning to cut cattle on horseback, supporting women to step out of their comfort zones, and waking to elk bugling on an overnight pack trip. There is something special about time spent at a dude ranch, especially the way you find yourself letting your guard down, relaxing, and truly connecting with yourself and your people. I’ve been going to and hosting travelers at Montana dude ranches for nearly 10 years. For me, they offer the best possible reset.
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