Flotillas - American Sailing

ASA flotilla in the San Juan Islands

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.

Every year, numerous ASA schools offer sailing flotillas in exotic and spectacular locations around the world. They take sailors of all skill levels where they not only have a great time, but also gain skill and confidence.

What is a flotilla?
A flotilla is a group of charter boats that travel a shared itinerary. A flotilla is led by an expert on the local waters who guides the other captains and their crews every step of the way. Often the captain of each individual boat is at liberty to follow the itinerary as closely or loosely as they desire, meaning you can spend an extra day in a favorite port, find a secluded beach for some impromptu swimming, or stick with the group.

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

Who are flotillas for?
Everyone can enjoy a flotilla. For experienced skippers, flotillas are a fun new challenge, and for relative newcomers, flotilla sailing is a great way to take away the intimidation factor of chartering in unfamiliar waters, while meeting fantastic new people and having an incredible experience they’ll remember all their lives. For many people, attending a flotilla hosted by an ASA school has opened the door for chartering on their own in places like the British Virgin Islands and the Mediterranean.

What I’ll remember most, aside from St. Martin itself, is the tight-knit bond that developed among the group, and particularly within the crews of the individual boats. Sailing with people, and living aboard with them, is a shared experience that you can’t replicate any other way. For me, that’s the greatest value of a flotilla. I can’t wait to do it again!

Discover why the “Christmas Winds” make December in the British Virgin Islands a sailing mecca! There is no better opportunity than our annual flotilla to expand your sailing skills, navigate to idyllic shores, and of course, experience the epitome of vacation perfection. The charm of the BVI’s lies in discovering the unique character of each pristine island in this volcanic archipelago.

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Join Sail Solomons while we spend 6 days and 7 nights aboard a Cruising Catamaran, in the beautiful US Virgin Islands. All sailing abilities welcome from novice to experienced. All boats will be skippered by an ASA Instructor/USCG Captain.

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Medsailing Adventures and its ASA Whitecaps Sailing school are organizing this exciting BVI flotilla. Our flotilla leader, Capt. Casey, used to live in the BVI and knows all the best places to visit, where to have the best snorkeling experience, where to have the most fun. He will share his profound knowledge of the history of the islands with our participants.

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Join our French Polynesia Flotilla and visit paradise on earth. It is only in sailing between the blue ocean and turquoise lagoons in the shadow of the majestic volcanic peaks as the ancient Polynesians did in their outrigger canoes, that one realizes the full majesty of Tahiti.

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Turkey, the mysteries of the Levant! Pashas and harems, Whirling Dervishes, the Bosporus, ruins of antique Greek, Roman, and Ephesians cities... the underground chapels and churches in Cappadocia? This country, at the crossroads of the East and the West, can also pride itself on some of the nicest sailing waters in the Mediterranean.

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Warm island sun and the lazy days of summer call for a getaway like no other. The charm of the British Virgin Islands lies in discovering the unique character of each pristine island in this volcanic archipelago. With lively culture and history on the four main islands topped only by the idyllic splendor of the 50+ smaller isles, every stop offers its own special magic.

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One of the best sailing areas in the entire world, the Ionian Sea and the famous group of islands situated off the Greek west coastline, a stunning part of the Mediterranean with sheltered islands, crystal clear waters and steady winds. Nature at its best!

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The San Juan Islands, located in the sheltered waters of Puget Sound in Washington State, offer a unique and incredibly scenic sailing experience. Many sailors prefer the San Juans to more traveled bareboat waters such as the British Virgin Islands or other tropical destinations.

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Tuscany, for many years, has been some of the most popular tourist attractions of Italy but is still relatively undiscovered by North American sailors. Here is a unique opportunity to combine a vacation in Italy with a sailing trip to explore the magical beauty of the Tyrrhenian Sea where you will sail to the islands of Elba and Capraia.

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This flotilla is for foodies and wine afficionados. Explore the antient city of Dubrovnik, Discover Ston and its well-preserved city walls and salt works. Sail the Peljesac Peninsula, revered for its unspoiled beached, endless coves and scenic valleys.

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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.

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