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.
DEC 10 & 12, 2024 • 4:30 PM PT
Essentials of Sailboat Electrical Systems
Learn the fundamentals of designing & optimizing DC power systems to meet your power needs
TUE DEC 17, 2024 • 4:30 PM PT
Safety At Sea
Learn how to avoid and overcome various safety scenarios encountered at sea
THU DEC 19, 2024 • 4:30 PM PT
Introduction to Celestial Navigation
Learn the fundamentals of celestial navigation and improve your seamanship skills
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.
THU JAN 09, 2025 • 4:30 PM PT
Knots For Sailors
Learn what knots to use and how to tie them via illustrations, discussion, and step-by-step videos
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.
FEB 01, 2025 • Long Beach, CA
Sail Trim & Boat Speed
An in-person seminar involving a full day of classroom-based instruction taught by an experienced North U sailing coach.
FEB 15, 2025 • Seattle, WA
Sail Trim & Boat Speed
An in-person seminar involving a full day of classroom-based instruction taught by an experienced North U sailing coach.
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.
FEB 22, 2025 • Chicago, IL
Racing Strategy, Tactics, & Rules
An in-person seminar involving a full day of classroom-based instruction taught by an experienced North U sailing coach.
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.
FEB 23, 2025 • Milwaukee, WI
Sail Trim & Boat Speed
An in-person seminar involving a full day of classroom-based instruction taught by an experienced North U sailing coach.
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.
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.
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.
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.
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.
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.
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.
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.
MAY 24 - 31, 2025 • 7 Days
Ionian Sea, Greece
Crystal-clear waters, breathtaking landscapes, mythical legends, ancient history, and Greek hospitality.
MAY 31 - JUN 07, 2025 • 8 Days
French Riviera
Departing from Port Les Cogolin, you’ll explore iconic destinations like St. Tropez, Bormes-les-Mimosas, and the islands of Porquerolles & Port-Cros.
MAY 31 - JUN 07, 2025 • 8 Days
Corfu, Greece
Enjoy the incomparable beauty of the Greek islands, the unique deep blue color of our sea, and the amazing Greek food.
JUN 07 - 14, 2025 • 7 Days
Amalfi Coast, Italy
Sail through the picturesque waters visiting hidden gems like Procida, Capri, and Positano.
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!
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.
JUN 21 - 28, 2025 • 8 Days
Athens, Greece
Discover hidden coves, swim in azure bays, and dock in charming Greek villages each evening, where local culture and cuisine await.
JUN 28 - JUL 05, 2025 • 8 Days
Corfu, Greece
Explore Corfu, Paxos, and Antipaxos and take in the stunning crystal-clear bays and local culture of charming villages along the way.
JUL 05 - 12, 2025 • 7 Days
Ionian Sea, Greece
Crystal-clear waters, breathtaking landscapes, mythical legends, ancient history, and Greek hospitality.
JUL 2025 • 8 DAYS
Explore Croatia aboard Cataleya
A week-long cruise of Croatia onboard a fully crewed luxury yacht.
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.
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.
AUG 30 - SEP 06, 2025 • 8 Days
Montenegro
Experience breathtaking scenery in the stunning Bay of Kotor and explore charming coastal towns rich in culture.
SEP 2025 • 8 DAYS
Explore Croatia aboard Cataleya
A week-long cruise of Croatia onboard a fully crewed luxury yacht.
SEP 06 - 13, 2025 • 8 Days
Dubrovnik to Split, Croatia
Join our "mile builder" flotilla for a stunning one-way journey from Dubrovnik to Trogir near Split.
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.
SEP 20 - 27, 2025 • 8 Days
Gulf of Fethiye, Turkey
Explore the breathtaking ruins of ancient Greek, Roman, and Ephesus cities on this Mediterranean flotilla
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
