In this edition of Behind the Stay, we meet Charlotte Lilley, the founder of The Retreat Company, a community-driven experience born from a lifelong love of the mountains. What began as casual trips with friends evolved into intimate retreats where women gather to ski, connect, and discover what true luxury means: intention, care, and freedom.
The Retreat Company wasn’t on my radar as a business when it started. It started with me planning ski trips – many ski trips, year over year.
I planned them for friends, both male and female, at first, and even for my colleagues at my places of work.
I wanted to get out of the city and go to different mountain towns to ski, and I was happy to plan for everyone.
I organized these trips because I genuinely love everything about a ski trip: the group breakfast, the skiing/snowboarding itself, the après and overall ski vibe, feeling tired in a good way, and then earning the fun group dinner we all make together.
I grew up in the California foothills, just a couple of hours from Lake Tahoe, and I developed a deep love for the mountains and started skiing at age three.
But like many, I followed a very conventional path: college, a career in tech, and climbing the corporate ladder in San Francisco. I spent over 15 years in sales and marketing at SaaS startups, which was a lot of fun.
Building The Retreat Company
I was in my corporate career when I started The Retreat Company.
As I was planning all the ski trips for friends and colleagues, I started wondering, what if I created these trips for more than just my friends and colleagues?
And so I launched The Retreat Company in 2018 with the mission to create outdoor experiences for women who want to experience adventure, empowerment, and connection.
Each retreat is designed with a lot of intention and is based on the location where the retreat is hosted.
We keep the groups small and we all stay in one house to create a strong connection over the time we’re together. Something about all staying in the house together creates that stronger bond.
Most of our guests come solo! Many women tell us that it’s hard to find other women to ski with. The retreats include activities like sound baths, cooking classes, yoga classes, guest speakers, a private chef, a goodie bag, and other surprises that we thoughtfully plan.
We’ve had women ski their first blue run, get off a chairlift confidently for the first time, or simply allow themselves to rest and be cared for. We always say that The Retreat Company is a compassionate environment to just come and be yourself!
Redefining Luxury in the Mountains
Fast forward 6 years after running The Retreat Company on the side to 2024, when I decided to leave my corporate tech job to work on The Ski Retreat full-time! It’s certainly been a journey, but it’s been rewarding.
People sometimes ask if The Retreat Company is considered a luxury experience, and the truth is: yes, I believe it is, but I don’t think it’s in the way that people often define luxury.
To us, luxury doesn’t mean excess; it’s more about intentionality. It means everything is high quality and thoughtfully curated from the beautiful homes we stay in, to the chef-prepared meals, to the care we put into experiences that are meaningful.
It’s the kind of luxury where women don’t have to make a decision once they arrive and we keep the groups small, which fosters connection and community.
Creating Space for Connection
Looking back, what started as a personal love for ski trips turned into something far bigger than I could have imagined.
The Retreat Company has become a space where women show up for themselves, and for each other. It’s not just about skiing, it’s so much more!
I’ve been lucky enough to see women try things they never thought they could do, create real friendships, and return home inspired in one way or another.
Looking Ahead
That’s what luxury means to me!
Being cared for, having the space to try new experiences, and creating meaningful connections.
Building that kind of experience for women who can’t sit still has been the most meaningful thing I’ve ever done, and I look forward to continuing to grow this community one retreat at a time!
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Charlotte Lilley is the founder of The Ski Retreat, an adventure organization for women who can’t sit still. Raised in the California foothills just a couple hours from Lake Tahoe, she began skiing at age three and has always felt most at home in the mountains.
