Flotillas

Paraty in Brazil, South America A Guided Flotilla

Brazil is one of the most popular destinations on many tourists’ bucket list, but still widely unknown for its sailing culture. Join us as we set sail on an amazing flotilla from Paraty.
From$2,190
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Islands of Belize, Central America A Guided Flotilla

Explore Belize’s paradise islands on your own private luxury catamaran. Learn sailing from ASA certified instructors & crew. Snorkel, kayak, and fish in crystal clear waters. Enjoy gourmet meals & exotic drinks prepared by your crew. Experience a different destination every day on this ultimate sailing vacation!
From$2,995
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2025

Lenny Shabes Sailing Festival ~ BVIs A Guided Flotilla

Join us for a week of sailing in paradise, as our late founder Lenny Shabes, set out to teach aspiring sailors to do. To pay tribute to all Lenny has done for the world of sailing, we are calling all sailors to partake in a week of festivities ranging from sundowners to regattas in the […]
From$2,499
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Turkey, Mediterranean A Guided Flotilla

Spirited sailing in the Gulf of Fethiye, turquoise waters that invite you for an invigorating swim, secluded anchorages to spend the night, small restaurants where you will be spoiled with amazing gastronomy. All this will make for an unforgettable flotilla experience.
From$2,095
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The Bahamas, Caribbean A Guided Flotilla

Join Whitecaps Sailing School in the Bahamas for an extraordinary sailing adventure. Explore turquoise waters, encounter dolphins, reefs, and sea turtles, all guided by expert ASA instructors.
From$2,300
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British Virgin Islands, Caribbean A Guided Flotilla

Join our vibrant flotilla for an unforgettable voyage through the BVI's azure waters. Enjoy daily sailing excursions, island hopping, and leisurely activities like snorkeling and beachcombing. Whether you're a seasoned sailor or a novice, this trip promises endless fun and relaxation in paradise.
From$2,450
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British Virgin Islands, Caribbean A Guided Flotilla

The BVIs are the perfect destination for your first charter experience. A flotilla gives you the support group that makes that first charter experience even easier. And the weather in late February in the BVIs is some of the best.
From$2,500
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Gulf Islands, British Columbia A Guided Flotilla

Join fellow sailors in cruising the charming east coast of Vancouver Island and the beautiful Gulf Islands. These islands boast sheltered waters, magnificent marine parks, quiet villages and welcoming marinas. Wildlife abounds on the land and in the sea, with deer, bald eagles, sea otters, seals, sea lions and orca whales commonplace.
From$1,700
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