ASA School Flotillas

ASA flotilla in the San Juan Islands
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!
Islands of Belize, Central America hosted by Belize Sailing Vacations
August 12th - 19th 2017 Starting from $2,695
ASA Flotilla
Sailing with Belize Sailing Vacation's ASA certified instructors & crew offers you the ultimate opportunity to explore the spectacular paradise islands that Belize has to offer, aboard your own private luxury catamaran. Sail daily to new destinations, while your private crew takes care of your every need: preparing & serving gourmet meals & exotic libations, helping you catch fresh lobster & local seafood for your dinner, launching kayaks, taking you on snorkeling excursions, and more!

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Cuba, Caribbean hosted by South Coast Sailing Adventures
August 19th - 26th 2017 Starting from $2,500
ASA Flotilla
Tantalizingly close but frozen in a bygone era, Cuba's cobblestone streets and deep-rooted culture are as inviting as the people. This is a special moment in history when you can still explore a place that has remained isolated and untouched by mass tourism and foreign involvement. SCSA joins Rockin’ Songwriters Island Radio on a unique people-to-people rally with round-trip sailing from Key West, Florida to Havana, Cuba this April!

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Balearic Islands, Mediterranean hosted by Sea Safaris Sailing School
September 2nd - 9th 2017 Starting from $1,250
ASA Flotilla
Explore the breathtakingly beautiful Balearic Island of Mallorca, drop the hook in hidden calas, dock at welcoming port, taste the unique Mediterranean cuisine and enjoy the legendary tourist attraction that is the City of Palma de Mallorca.

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Martha’s Vineyard & the Cape Cod Islands, New England, USA hosted by Narragansett Sailing School
September 9th - 16th 2017 Starting from from $1,995
ASA Flotilla
Let’s go to Martha’s Vineyard and the Cape Cod Islands! Captained by an ASA instructor who has sailed these waters for over 30 years. September is the BEST month to see these quaint New England villages. We will stay in the harbors of Cuttyhunk and Vineyard Haven, plus visit some of the historical towns in Rhode Island including Newport and Bristol. You can count on incredible seafood, lots of history, and fabulous winds for sailing.

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British Virgin Islands, Caribbean hosted by South Coast Sailing Adventures
December 7th - 17th 2017 Starting from $1,795
ASA Flotilla
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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