Experience

Upcoming Cruises and Flotillas

Islands of Belize, Central America A Guided Flotilla

Belize Sailing Vacations
Availability : Jun - Dec 2024

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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Grand Tour of New England Aboard Arabella A LUXURY CRUISE

American Sailing
Availability : August 2024

From the moment you board Arabella in Newport, Rhode Island, the tone is set for a sailing adventure. Your week aboard Arabella will be filled with full sails on the way to Martha’s Vineyard, Nantucket, and Cuttyhunk. This is more than a sailing vacation; it’s an adventure for the soul.

From$2,200
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Dalmatian Islands of Croatia, Mediterranean A Guided Flotilla

Whitecaps Sailing School
Availability : Aug 31 - Sep 7   |   Sep 7 - 14, 2024

Join our most popular itinerary in Croatia with visits to islands like Hvar, Brac, and Vis. This itinerary, which we started in 2009, has constantly remained the most popular choice for first-time sailors in Croatia.

From$2,150
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EXPLORE CROATIA ABOARD CATALEYA A LUXURY CRUISE

American Sailing
Availability : Sep 14, 2024

Welcome aboard Cataleya a 30 meter luxury sailing yacht which will be your home for 8 days as you explore the Dalmation coast of Croatia. This trip will include stops in Split, Hvar, Korcula as well as a few anchorages that are the secrets of the captain and the crew. Join us on a once-in-a-lifetime sailing vacation.

From$2,800
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EXPLORE MALLORCA ABOARD CHRONOS A LUXURY CRUISE

American Sailing
Availability : Oct 21, 2024

Embark on a 6-day luxury sailing adventure aboard Chronos Yacht, exploring Mallorca to Menorca with American Sailing. Enjoy personalized service, secluded coves, and stunning coastlines with a small, passionate group. This intimate voyage offers full-board luxury, breathtaking views, and unique experiences in the heart of the Balearic Islands. Set sail for an unforgettable journey this fall.

From$2,975
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The Bahamas, Caribbean A Guided Flotilla

Whitecaps Sailing School
Availability : Dec 7-14, 2024

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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A BVI ESCAPE ABOARD ARABELLA A LUXURY CRUISE

American Sailing
Availability : Dec 2024 | Jan 2025 | Feb 2025

Embark on a transformative journey through the British Virgin Islands aboard Arabella with American Sailing. From the lively shores of Jost Van Dyke to the serene beauty of Virgin Gorda, every moment is promised to be infused with laughter, camaraderie, and pure joy. Lose yourself in the rhythm of island life, where each day brings new adventures and lifelong friendships. Your dream itinerary awaits – let Arabella be your guide through paradise.

From$2,550
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British Virgin Islands, Caribbean A Guided Flotilla

Annapolis Sailing School
Availability : Jan 31-Feb 7 & Feb 8-Feb 15

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 Learn-To-Sail Vacation

Annapolis Sailing School
Availability : Jan 31-Feb 7 & Feb 8-Feb 15, 2025
104 / 114

Embark on a sailing adventure through the picturesque BVI while earning your ASA 104 and 144 credentials. Our seasoned skippers will guide you through every aspect of sailing, from provisioning to navigation, ensuring a comprehensive learning experience amidst stunning island backdrops.

From$2,450
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