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.

4 CLASS SERIES • OCTOBER 2024

Racing Strategy, Tactics, and Rules

This series of four online classes teaches the strategy and tactics you need to turn your speed into a podium finish.

ANNAPOLIS, MD • OCT 11-13, 2024

Live Seminar Series

Join us during the Annapolis Boat Show for live, in-person seminars led by some of the world’s most esteemed and well-known sailors covering an array of topics.

Annapolis, MD • OCT 11, 2024

Secrets To Successful Cruising

For cruisers and aspiring cruisers intrigued by the secrets to setting sail with confidence and joy. Learn self-sufficiency, how to navigate the challenges at sea, boat maintenance, and more.

Annapolis, MD • OCT 11, 2024

How To Sail Around The World

Learn tips, tricks, and shortcuts for launching a safe and successful circumnavigation in this comprehensive, information-packed live seminar on How To Sail Around The World.

Annapolis, MD • OCT 12, 2024

Cruise With Confidence

Whether you're dreaming of setting sail or living the liveaboard life, this live seminar will offer valuable insights to cruise with confidence & clarity for successful extended cruising.

Annapolis, MD • OCT 12, 2024

Guide To Boat Buying

Gain insight on how to find the right boat with current market prices & trends. Learn how to navigate the purchase process & learn necessary procedures for selecting an ideal sailing yacht.

Annapolis, MD • OCT 13, 2024

How To Troubleshoot & Fix Common Diesel Engine Problems

Unlock the secrets of diesel engine troubleshooting. Perfect for current or future boat owners, learn how to diagnose and fix common diesel engine issues.

Annapolis, MD • OCT 13, 2024

Electrical Systems Troubleshooting For Boaters

Dive into common boat electrical system issues and learn how to maximize solar power utilization to enhance onboard life and reduce reliance on fossil fuels.

OCT 22 & 24, 2024 • 4:30 PM PT

Introduction to Marine Diesel

Learn about internal combustion and how to troubleshoot, winterize, and maintain your engine

TUE OCT 29, 2024 • 4:30 PM PT

Smart Storage Hacks for Life at Sea

Innovative ideas to help you create an enjoyable, well-organized living space aboard your sailboat

TUE NOV 05, 2024 • 4:30 PM PT

Watchkeeping & Passage Planning

Learn how preparation and good routines help make multi-day passages safe and fun

NOV 2024

Islands of Belize

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

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.

DEC 2024

Islands of Belize

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

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.

5 Day Clinics • FEB / MAR / APR 2025

Virgin Islands | Florida | Texas

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

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.

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 - 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 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.

JUL 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.

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.