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 • JUL 16 • 4:30PM PT

Understanding The Vessel Survey Process

Confidently navigate boat buying! This online course will help demystify the marine survey process.

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THU • JUL 18 • 4:30PM PT

Hurricane Readiness: A Blueprint for Boaters

Learn how to prepare your boat for hurricanes with proven strategies and detailed planning.

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TUE • JUL 23 • 4:30PM PT

Short-Handed Sailing

Master short-handed sailing with John Neal. Learn essential skills and strategies for navigating with a small crew.

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JUL 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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AUG / SEP • 7 DAYS • LIMITED SPOTS

Grand Tour of New England

Join us aboard Arabella, a 157-foot mega yacht, to explore all the sights of Martha’s Vineyard, Nantucket, and Cuttyhunk.
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AUG 2024

Gastro-Sail, Croatia

Explore the ancient city of Dubrovnik, Discover Ston & its well-preserved city walls and salt works.

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AUG 2024

Dalmatian Islands, Croatia

A sailor’s paradise with crystal clear waters, picturesque fishing villages, and scenic coves for anchoring.
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SEP 2024

Turkey

Turquoise waters, secluded anchorages, small restaurants, and amazing gastronomy is the recipe for a memorable flotilla vacation.
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SEATTLE, WA • SEP 18-22, 2024

On-The-Water Sailing Clinic

Master racing trim, helming, and boat handling with practical on-water training and shoreside seminars taught by seasoned coaches.
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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.
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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. 
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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.
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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.
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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.
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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. 
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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.
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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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DEC 2024

British Virgin Islands, Caribbean

Discover why the “Christmas Winds” make December in the BVI a sailing mecca!

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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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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 15 - MAR 01 • 2025

Tahiti & The Society Islands, French Polynesia

Experience perfect sailing conditions, volcanic peaks, turquoise lagoons, and vibrant coral reefs during this two-week-long flotilla hosted by South Coast Sailing Adventures.
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JUL 2025 • 8 DAYS • 1 SPOT REMAINING

Explore The Amalfi Coast Aboard Chronos

Join American Sailing as we discover the Amalfi Coast (Amalfi, Positano, Capri, and more) from Luxury Yacht Chronos.