Flotillas

Dalmatian Islands of Croatia, Mediterranean A Guided Flotilla

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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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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Victoria & the Gulf Islands, Pacific Northwest A Guided Flotilla

Join fellow sailors for a week cruising the beautiful San Juan and Canadian Gulf Islands to Victoria, BC. The San Juan and adjacent Gulf islands are a cruising paradise boasting 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, […]
From$900
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Greece, Mediterranean A Guided Flotilla

Join American Sailing and Fairwinds Sailing Greece on a journey from Corfu through the Corfu Islands. Our local captains from Fairwinds Sailing will take us to their favorite anchorages and introduce us to Greece as seen through their eyes. Corfu Island is in the north Ionian Sea, between Italy and Greece (Greek “Ιόνιο Πέλαγος” – […]
From$1,875
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Italy’s Amalfi Coast, Mediterranean A Guided Flotilla

Sail the beautiful waters of the Amalfi Coast on this flotilla led by an experienced captain. You will have the opportunity to explore the amazing coastline of Italy and enjoy the local cuisine and culture.
From$2,095
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INVITE ONLY

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$1,250
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Greece & The Aegean Sea, Mediterranean A Guided Flotilla

Athens Sailing Academy and American Sailing invite you to join us as we sail the beautiful Blue Aegean Sea. Depart from our base on Poros Island, just off Athens and discover ancient Castles and quaint anchorages and villages. You can choose from our large selection of Jeanneau Yachts, ranging from 34ft to 55ft.
From$1,400
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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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Greece & The Saronic Gulf, Mediterranean A Guided Flotilla

Combine spirited sailing with ancient Greek history, mythology, legendary Greek hospitality and gastronomy, and you have the formula for a memorable flotilla vacation.
From$2,095
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British Virgin Islands, Caribbean A Guided Flotilla

Warm island sun and the lazy days of summer call for a getaway like no other! The stunning 55+ islands and cays that comprise the British Virgin Islands have two fantastic assets – accessibility and virgin beauty. Discover your “sit-back-and-relax” mode on our 11 Days and 10 Nights flotilla.
From$2,395
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British Virgin Islands, Caribbean A Guided Flotilla

Discover why the “Christmas Winds” make December in the British Virgin Islands a sailing mecca! There is no better opportunity than our annual winter flotilla to expand your sailing skills, navigate to idyllic shores, and of course, experience the epitome of vacation perfection.
From$2,395
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Croatia, The Dalmatian Islands A Guided Flotilla

Set sail amidst the mesmerizing Dalmatian Islands of Croatia with Delta Sailing School! An ASA-accredited school, Delta Sailing School’s flotilla adventures cater to both novices and seasoned sailors alike, offering the opportunity to enhance your sailing skills and knowledge.
From$2,100
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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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PRICE INCREASES 7/1/24

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$2,350
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