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November 3rd - 10th | Starting at $2,800Sailing Martinique & St Lucia
What to Expect:Leave the ordinary behind and experience the Caribbean the way few people ever do. Spend seven unforgettable days sailing between tropical islands, swimming in crystal-clear waters, exploring hidden beaches, and sharing incredible adventures with a small group of like-minded travelers.
From snorkeling vibrant reefs and hiking lush landscapes to horseback riding, sunset sails, and waterfront dinners, every day offers a new opportunity to explore, connect, and create lasting memories. With breakfast and lunch prepared onboard, your accommodations and sailing logistics taken care of, all you have to do is show up ready for adventure.
⛵ Curated AdventureEvery day brings something new—from sailing between Caribbean islands and snorkeling vibrant reefs to hiking lush trails, horseback riding, and discovering hidden beaches. We've crafted an itinerary that balances adventure with time to relax.
🌊 Small Group ExperienceWith only 8 guest spots, you'll enjoy an intimate atmosphere where meaningful friendships are formed, shared meals become lasting memories, and every adventure feels personal—not crowded.
☀️ Stress-Free TravelFrom your accommodations aboard a luxury catamaran to breakfast, lunch, sailing logistics, fuel, and mooring fees, we've taken care of the details so you can simply arrive and enjoy the journey.
⚓ Experienced HostsHosted by Chloe Hardy and Cade Chudy, you'll be guided through an unforgettable week of exploration, connection, and adventure. Whether it's finding the best hidden coves or sharing sunset dinners ashore, we're here to make your Caribbean experience seamless and memorable.
Trade the ordinary for seven unforgettable days exploring the Caribbean by sail, sea, and shore.
Day OneArrive & Meet
As everyone arrives, we take time to settle in, get comfortable, and begin connecting with those around us. The journey starts here.
Check-In9:00 – 9:30am
Group Activity11:00am
Lunch Break12:30pm
Creative Workshop2:00pm
Dinner6:30pm
Day TwoSet Intentions & Reflect
Together, we pause to consider our goals, hopes, and direction. This is about aligning with ourselves and with the journey ahead. This is a chance to reconnect with what brought you here—your questions, your hopes, your turning points—and consider how they’ve shifted or deepened.
Check-In9:00 – 9:30am
Group Activity11:00am
Lunch Break12:30pm
Creative Workshop2:00pm
Dinner6:30pm
Day ThreeLook Forward & Wrap Up
We explore the possibilities beyond this moment, making space for growth, action, and forward momentum. As we end our time together, we honor the experience, the growth, and the connections made along the way.
Check-In9:00 – 9:30am
Group Activity11:00am
Lunch Break12:30pm
Creative Workshop2:00pm
Dinner6:30pm
How It Works-
Browse our upcoming events to find the one that feels right for you. We host events year-round in all different locations and climates.
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Sign up and pay all required fees to reserve your spot. If plans change, you can cancel up to 14 days before the retreat start to receive a 50% refund.
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After booking, we'll send you a Welcome Packet with everything you need to know—detailed schedules, packing list recommendations, add-ons to consider, and more.
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We'd recommend booking your transportation to and from the event as soon as possible, to ensure you can arrive without any complications or delays.
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Now all that's left to do is pack your bags and get excited for your new adventure.