What is a Flotilla?

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

What is a flotilla?

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.

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. They provide a way for sailors to meet fantastic new people and have an incredible experience they’ll remember all their lives. For many, attending a flotilla has given them the confidence to go chartering on their own.
What I’ll remember most, aside from St. Martin itself, is the tight-knit bond that developed among the group, 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!

UPCOMING FLOTILLAS

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.
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TUE NOV 12, 2024 • 4:30 PM PT

Earning Your USCG Captains License

Learn what it takes, why you need it, and the process for obtaining Your US Coast Guards Captain’s License
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WED NOV 13, 2024 • 4:30 PM PT

Bareboat Chartering in Greece

The ultimate guide to chartering the crystal-clear waters of Greece
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NOV 2024

Islands of Belize

Experience the beauty of Belize on this sailing flotilla. Explore new locations every day, enjoy snorkeling, and more.

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TUE NOV 19, 2024 • 4:30 PM PT

Introduction to Sailboat Racing

Sailors of all levels can learn how to get started racing sailboats
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THU NOV 21, 2024 • 4:30 PM PT

Boating Rules & Navigation Aids

Learn the rules and regulations that all boaters must know to navigate safely.
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TUE NOV 26, 2024 • 4:30 PM PT

Cruising from Grenada to St. Lucia

Learn the nuances of island hopping through the Caribbean's Windward Islands
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DEC 03 & 05, 2024 • 4:30 PM PT

Marine Weather Planning

Learn how to refine your navigation & route planning skills by incorporating marine weather, observations, & technology.
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TUE DEC 17, 2024 • 4:30 PM PT

Safety At Sea

Learn how to avoid and overcome various safety scenarios encountered at sea
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THU DEC 19, 2024 • 4:30 PM PT

Introduction to Celestial Navigation

Learn the fundamentals of celestial navigation and improve your seamanship skills
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DEC 2024

The Bahamas, Caribbean

Explore turquoise waters, encounter dolphins, reefs, and sea turtles, during this extraordinary Bahamas flotilla - guided by the experts at Whitecaps Sailing.
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DEC 2024

Islands of Belize

Experience the beauty of Belize on this sailing flotilla. Explore new locations every day, enjoy snorkeling, and more.

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UPCOMING FLOTILLAS

All Around The World

Join a flotilla and enjoy the freedom of skippering your own boat with added support and advice from an expert sailor to help with navigation and local weather.
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FL | MD | TX | VI • 2025

On-The-Water Sailing Clinics

Amazing venues hosting a week of on-water training and shoreside seminars to help you master sail trim, helming, and boat handling.
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JAN 31 - FEB 7 • 2025

British Virgin Islands, Caribbean

Join Annapolis Sailing School for an unforgettable voyage through the British Virgin Island's azure waters. Enjoy daily sailing excursions, island hopping, and leisurely activities like snorkeling and beachcombing.
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JAN 8 - FEB 15 • 2025

British Virgin Islands, Caribbean

Join Annapolis Sailing School for the adventure of a lifetime in a tropical paradise. Sail through azure waters, indulge in leisurely activities like snorkeling and beachcombing while island hopping. 
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FEB 22 - MAR 01, 2025 • 8 Days

British Virgin Islands, Caribbean

The BVIs are the perfect destination for your first charter experience and the weather in February in the BVI is some of the best.
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FEB 24-28, 2025 • 5 Day Clinic

St. Thomas, Virgin Islands

A week of on-water training and shoreside seminars to help you master sail trim, helming, and boat handling.
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MAR 16-23 2025 • 8 DAYS

Sailing the Grenadines Aboard Chronos

Join American Sailing on an unforgettable sailing adventure aboard the elegant Chronos, exploring the stunning Grenadines.
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MAR 24-28, 2025 • 5 Day Womens Clinic

St. Petersburg, Florida

A week of on-water training and shoreside seminars to help you master sail trim, helming, and boat handling.
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APR 05-12, 2025 • 8 Days

Paraty, Brazil

A beautiful place with intriguing history, culture, and mouth-watering cuisine. Join us as we set sail on an amazing flotilla from Paraty.
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APR 07-11, 2025 • 5 Day Clinic

Austin, Texas

A week of on-water training and shoreside seminars to help you master sail trim, helming, and boat handling.
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APR 26 - MAY 02, 2025 • 7 Days

La Paz, Mexico

The "Aquarium of the World," offers crystal-clear turquoise waters, calm seas, and stunning, unspoiled islands.
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MAY 14-18, 2025 • 5 Day Clinic

Annapolis, Maryland

A week of on-water training and shoreside seminars to help you master sail trim, helming, and boat handling.
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MAY 24 - 31, 2025 • 7 Days

Ionian Sea, Greece

Crystal-clear waters, breathtaking landscapes, mythical legends, ancient history, and Greek hospitality.
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JUN 2025 • 7 DAYS

Lenny Shabes Sailing Festival • BVI

American Sailing presents an epic flotilla experience in the British Virgin Islands. It’s going to be an action-packed sailing adventure!
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JUN 21-27, 2025 • 8 Days

Gulf Islands, British Columbia

Cruise the charming coast of Vancouver Island and the beautiful Gulf Islands. These islands boast sheltered waters, magnificent marine parks, quiet villages, and welcoming marinas.
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JUL 05 - 12, 2025 • 7 Days

Ionian Sea, Greece

Crystal-clear waters, breathtaking landscapes, mythical legends, ancient history, and Greek hospitality.
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JUN 07 - 14, 2025 • 7 Days

Amalfi Coast, Italy

Sail through the picturesque waters visiting hidden gems like Procida, Capri, and Positano.
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JUL 2025 • 8 DAYS

Explore Croatia aboard Cataleya

A week-long cruise of Croatia onboard a fully crewed luxury yacht.
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JUL 2025 • 8 DAYS

Explore The Amalfi Coast Aboard Chronos

Join American Sailing as we discover the Amalfi Coast (Amalfi, Positano, Capri, and more) from Luxury Yacht Chronos.
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AUG 23 - 30, 2025 • 7 Days

Central Dalmatian Islands, Croatia

Explore the stunning islands of Hvar, Vis, and other hidden gems along Croatia’s pristine coastline.
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SEP 2025 • 8 DAYS

Explore Croatia aboard Cataleya

A week-long cruise of Croatia onboard a fully crewed luxury yacht.
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SEP 13 - 20, 2025 • 7 Days

Central Dalmatian Islands, Croatia

Explore the stunning islands of Hvar, Vis, and other hidden gems along Croatia’s pristine coastline.
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OCT 2025 • 8 DAYS

St Tropez to Mallorca Aboard Chronos

Set sail from the glamorous port of St. Tropez toward Marseille and onwards across the Mediterranean to the Balearic Islands