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!
Tuscany, Italy, Mediterranean hosted by Sea Safaris Sailing School
September 14th - 21st 2019 Starting from $1,550
ASA Flotilla
Tuscany has, for many, years been one 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 Thyrrenian Sea where you will sail to the islands of Elba and Capraia.

More Information

Islands of Belize, Central America hosted by Belize Sailing Vacations
October 12th - 19th 2019 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!

More Information

Martha's Vineyard / Bermuda, New England, USA hosted by Charter House
October 15th - 22nd 2019 Starting from $1,800
ASA Flotilla
Sailing from Martha’s Vineyard, Massachusetts to Bermuda aboard a luxury, blue water cruising yacht offers you the ultimate live-aboard sailing experience! Perfect for students seeking experience in between courses or sailors considering a cruising lifestyle of their own, this trip allows sailors a chance to explore the planning, preparation and techniques necessary for a longer, offshore cruise.

More Information

Bermuda - St. Martin, Caribbean hosted by Charter House
November 14th - 22nd 2019 Starting from $1,800
ASA Flotilla
This adventurous ocean passage offers sailors an exceptional opportunity to explore four Caribbean island-nations and gain more knowledge, training and experience with liveaboard/cruising sailing! Fly into Bermuda and experience the old-world charm and beauty of this British island, then set sail on an exciting voyage thru the Caribbean.

More Information

Islands of Belize, Central America hosted by Belize Sailing Vacations
November 23rd - 23rd 2019 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!

More Information

British Virgin Islands, Caribbean hosted by South Coast Sailing Adventures
December 5th - 15th 2019 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.

More Information

Islands of Belize, Central America hosted by Belize Sailing Vacations
December 14th - 21st 2019 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!

More Information

Gulf Islands of British Columbia, Pacific Northwest, USA & Canada hosted by San Juan Sailing
June 20th - 26th 2020 Starting from $1,350
ASA Flotilla
The San Juan Islands of northwest Washington and the adjacent Vancouver Island of British Columbia are a cruising paradise. These islands boast sheltered waters, magnificent marine parks, quiet villages and an abundance of marinas. Wildlife abounds on the land and in the sea, with deer, bald eagles, seals, sea lions and orca whales. Our sailing route will include overnights at anchor or moorings, as well as docked in marinas at small villages or resorts.

More Information