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!
May 13th - 20th 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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May 14th - 22nd 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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June 8th - 18th 2017 Starting from $1,795
ASA Flotilla
Warm island sun and the lazy days of summer call for a getaway like no other. The charm of the British Virgin Island lies in discovering 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. Discover your “sit-back-and-relax” mode on Tortola; be mesmerized by Virgin Gorda’s natural granite pillars or marvel at the rugged scenery and colorful folklore of Jost Van Dyke.

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June 10th - 24th 2017 Starting from $1,000
ASA Flotilla
Sail the breathtaking Dalmatian Coast of Croatia! Let us book a yacht for your friends and family and follow the other yachts in the flotilla, or book a cabin on a shared flotilla yacht. We mix and match crew members according to their sailing experience, shared interests and personal chemistry.

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June 17th - 24th 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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June 23rd - 30th 2017 Starting from $1,116
ASA Flotilla
Departing from Bellingham, Washington, we sail the protected waters of the Salish Sea to the city of Victoria BC, tying up at famous Empress Hotel in the heart of the city. Enroute we anchor at secluded Lopez Island for hiking & exploring. We return by way of Friday Harbor on San Juan Island & the sparkling Rosario Resort on Orcas Island. A raft-up & beach barbecue on Lummi Island are also in store. Weather is generally mild in June, with little rain. Limited to 12 boats and books up early. Come sail with us!

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July 1st - 7th 2017 Starting from from $950
ASA Flotilla
Relax and enjoy our one week flotilla sailing around some of the Canary Islands best loved and stunning locations. Visit Tenerife, Lanzarote, Fuerteventura, Gran Canaria, La Gomera and more. The days can be long, the winds can be challenging but our cruises are very popular and will give you a great sense of achievement. You can come on one of our skippered boats, or charter a boat and join the flotilla.

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July 8th - 14th 2017 Starting from from $950
ASA Flotilla
Our one week cruise will enable you to explore the peaceful and stunning western Canary Islands. Visit Tenerife north, La Palma, El Hierr, La Gomera, and more. The days can be long, the winds can be challenging but our skippered cruises are very popular and will give you not only a fantastic adventure but an awesome sense of achievement.

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July 15th - 22nd 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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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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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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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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