What is a Flotilla, Anyway?
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If you've been curious about joining one of our Share the Sail adventures, you may have seen the word flotilla pop up and wondered what it actually means.
In short: a flotilla is a group of boats sailing the same route, loosely together. Think of it as the perfect balance between independence and community—like a road trip on the water, with built-in friends and flexibility.
Not a Cruise. Not Just a Charter. Better.
Unlike a cruise ship, you’re not following a rigid itinerary with 3,000 strangers. And unlike a private charter, you're not on your own with zero connection to others. A flotilla gives you the best of both worlds—you have your own private cabin on a captained catamaran, but you're also part of a laid-back fleet of fellow sailors exploring the same region.
How it Works
We typically sail together in the morning or early afternoon, then anchor in the same area each night. Sometimes we raft up together for sundowners, sometimes we anchor separately for a little peace and quiet—then dinghy over to meet for fun!
Each boat has its own pace and personality, and that’s part of the charm. You may snorkel with one boat crew in the morning, then hop over to another for a theme night or potluck dinner. Want to relax with your book onboard all day? That’s fine too. No pressure. No rigid plans. Just connection when you want it.
What Makes It Fun
Theme nights: From pirate parties to tropical dress-up, we love a reason to laugh and gather.
Dinghy meetups: Grab your crew and zip over to another boat for cocktails or dessert under the stars.
Shared adventures: Snorkeling, hiking, and beach days are more fun when you have a whole crew to enjoy it with.
New friends: You’ll be surprised how quickly strangers become sailing family.
Why We Love It
A flotilla lets you experience the magic of a sailing lifestyle—without needing sailing experience. You get the joy of life on the water, new destinations, and new friendships, all wrapped in a tropical breeze.
So if you're dreaming of turquoise water, sunset sails, and a built-in community, welcome aboard. This is flotilla life—and we think you’ll love it.
READY to share the sail with us?
Whether you're ready to book your spot or just have a few questions, we’d love to hear from you. Share the Sail is all about community, adventure, and making the cruising lifestyle more accessible—no experience necessary. Let’s get you on the water!
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About Share the Sail
At Latitudes & Attitudes, we believe sailing should be more than a trip—it should be a shared adventure. That’s why we created Share the Sail: a chance for cruisers, dreamers, and salty souls to explore the world together by boat.
Whether you're an old salt or brand new to the sailing life, STS brings you into a laid-back flotilla of fun, hosted by the Lats & Atts crew. We've sailed everywhere from the British Virgin Islands to Mallorca, and in 2026, we’re setting course for Tahiti and the stunning islands of French Polynesia.
No stress. No planning. Just incredible sailing, unforgettable sunsets, and friendships that last far beyond the dock.
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Whether you’re dreaming of turquoise anchorages, sunset sails, or unforgettable moments at sea, our group adventures deliver the ultimate cruising experience.
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