Experience

FLOTILLAS

Flotillas really are the best of both worlds.
All the freedom of a bareboat charter combined with the comfort and camaraderie of group travel.

Flotilla sailing charter vacations bring together a fleet of sailboats, each operating independently with its own crew, along with a lead boat and flotilla leader who knows the local area well. By joining a flotilla, you can enjoy the freedom of skippering your own boat but have comfort in knowing that support and advice are on hand to help with navigation and local weather. They provide a way for sailors to meet fantastic new people and have an incredible experience they’ll remember all their lives. For many, attending a flotilla has given them the confidence to go chartering on their own.

SOLD OUT

Italy’s Amalfi Coast, Mediterranean A Guided Flotilla

Whitecaps Sailing School
Availability : May 25-June 1, 2024

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.

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Greece & The Aegean Sea, Mediterranean A Guided Flotilla

Athens Sailing School
Availability : May 25-June 1, 2024

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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Croatia, The Dalmatian Islands A Guided Flotilla

Delta Sailing School
Availability : May 25-June 22, 2024

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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Greece, Mediterranean A Guided Flotilla

Fair Winds Sailing
Availability : June 8-15, 2024

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” – Italian “Mare Ionio”). Corfu is considered one of the finest and most cosmopolitan islands in the Mediterranean. 

From$1,875
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British Virgin Islands, Caribbean A Guided Flotilla

South Coast Sailing Adventures
Availability : June 6-16, 2024

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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Greece & The Saronic Gulf, Mediterranean A Guided Flotilla

WHITECAPS SAILING SCHOOL
Availability : June 15-22, 2024

Combine spirited sailing with ancient Greek history, mythology, legendary Greek hospitality and gastronomy, and you have the formula for a memorable flotilla vacation.

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INVITE ONLY

Lenny Shabes Sailing Festival ~ BVIs A Guided Flotilla

American Sailing
Availability : June 16-22, 2024

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 beautiful BVI’s.

From$1,250
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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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Victoria & the Gulf Islands, Pacific Northwest A Guided Flotilla

San Juan Sailing
Availability : June 22-28, 2024

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, and orca whales commonplace.

From$900
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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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Turkey, Mediterranean A Guided Flotilla

Whitecaps Sailing School
Availability : September 21-28, 2024

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.

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British Virgin Islands, Caribbean A Guided Flotilla

South Coast Sailing Adventures
Availability : December 5-15, 2024

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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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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PRICE INCREASES 7/1/24

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$2,350
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