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 9th - 15th 2020
Starting from $2,595
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!
June 4th - 14th 2020
Starting from $1,795
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.
June 13th - 19th 2020
Starting from $2,595
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!
June 20th - 26th 2020
Starting from $1,350
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.
July 18th - 24th 2020
Starting from $2,595
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!
August 15th - 21st 2020
Starting from $2,595
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!
August 22nd - 29th 2020
Starting from $1,650
Sea Safaris Sailing School in coordination with Med Sailing Adventures and the American Sailing Association offer you an unforgettable sailing vacation of a lifetime. Sail away with us and discover the uniquely rich palette of colors, sights, flavors and smells that are so typical of the Mediterranean. Explore some of the thousands of islands of the Dalmatian coast of Croatia. Enjoy memorable gastronomic experiences like the Croatian Peka and mussels Bouzara.
August 29th - September 5th 2020
Starting from $1,650
One of ASA's most popular flotillas. Visit the central Dalmatian islands of Solta, Vis, Hvar and Brac. Experience the great sailing waters of Croatia, the fascinating culture and history, drop the hook in secluded anchorages, visit charming fishing villages and historic cities and discover gastronomic delights and local wines.
September 12th - 19th 2020
Starting from $1,995
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.
September 12th - 19th 2020
Starting from $1,650
Sail with Capt. Jean & "Admiral" Mila from "Games of Thrones" Dubrovnik to the walled medieval city of Korcula, home of Marco Polo. Enjoy fabulous food and excellent local wines and share the fellowship of sailing with new friends.
September 19th - 26th 2020
Starting from $1,650
Sail from historic "Games of Thrones" Dubrovnik to the neighboring country of Montenegro. Montenegro is still undiscovered by most American sailors and we will show you the amazing beauty of the Bay of Kotor, the largest fjord-like bay in southern Europe.
October 3rd - 9th 2020
Starting from $1,650
Take a slow houseboat trip down the lazy Sile river from Treviso to the Venice Lagoon and take in the majestic sights of Venice from your comfortable modern houseboat yacht. Share a yacht or book one for yourself and friends or family.
November 27th - December 6th 2020
Starting from $1,795
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.
Tahiti, Raiatea, Taha’a, Huahine, Bora Bora, French Polynesia hosted by South Coast Sailing Adventures
February 20th - March 6th 2021
Starting from $6,000
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.