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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DEC 5 & 7 • DEC 12 & 14

ASA 102: Keelboat 2 - Online Prep

Prepare for the exciting new on-the-water ASA 102 certification, coming soon to an American Sailing School near you.

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DEC 12 & 14 • 7:00 PM (PT)

ASA 102: Keelboat 2 - Online Prep

Prepare for the exciting new on-the-water ASA 102 certification, coming soon to an American Sailing School near you.

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DEC 19 • 4:30 PM (PT)

Bareboat Chartering in Greece

Learn about the geography, the climate, the sailing season, the prevailing winds, and lots more.

North U Sail Trim Seminar

JAN 20 • Vancouver, BC

Sail Trim & Boat Speed

Learn about sail dynamics, sail trim, and optimizing performance for various wind conditions at this in-person seminar.

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JAN 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 27 • Long Beach, CA

Racing Strategy, Tactics & Rules

Learn techniques, tactics, and decision-making skills to help your performance on the race course at this in-person seminar

North U Sail Trim Seminar

FEB 4 • Indianapolis, IN

Sail Trim & Boat Speed

Learn about sail dynamics, sail trim, and optimizing performance for various wind conditions at this in-person seminar.

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FEB / MAR / APR 2024

Virgins Islands / Florida / Texas

Master racing trim, helming, and boat handling with experienced coaches onboard high-performance sailboats.
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FEB 2024

St Thomas, VI

Master racing trim, helming, and boat handling with experienced coaches onboard high-performance IC-24s
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FEB 2024

St Petersburg, FL

Compete in the Helly Hansen Sailing World Regatta with experienced coaches onboard high-performance J/70s.
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Feb 2024

Tahiti, French Polynesia

Those who fly into the islands and stay at hotels experience only a part of the magic of these islands.

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FEB 2024

British Virgin Islands

Discover the beauty of the British Virgin Islands while enjoying the spaciousness, speed, stability, and shallow draft that catamarans offer.

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MAR 24 • Grapevine, TX

Racing Strategy, Tactics & Rules

Learn techniques, tactics, and decision-making skills to help your performance on the race course at this in-person seminar

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MAR 2024

St Thomas, VI

Master racing trim, helming, and boat handling with experienced coaches onboard high-performance IC-24 sailboats
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MAR 2024

St Petersburg, FL

Master racing trim, helming, and boat handling with experienced coaches onboard high-performance J/70 sailboats
North U Sail Trim Seminar

APR 6 • Nepean, ON

Sail Trim & Boat Speed

Learn about sail dynamics, sail trim, and optimizing performance for various wind conditions at this in-person seminar.

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APR 6 • Halifax, NS

Racing Strategy, Tactics & Rules

Learn techniques, tactics, and decision-making skills to help your performance on the race course at this in-person seminar

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Apr 2024

Paraty, Brazil in South America

Sail in pristine waters along the coast lined with tropical rainforest and white and golden sandy beaches.
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Apr 2024

Austin, TX

Master racing trim, helming, and boat handling with experienced coaches onboard high-performance J/80 sailboats
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APR 14 • Park City, UT

Racing Strategy, Tactics & Rules

Learn techniques, tactics, and decision-making skills to help your performance on the race course at this in-person seminar

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Apr 2024

Charleston, SC

Compete in Charleston Race Week and master every facet of regatta success with experienced coaches onboard J/22s.
North U Sail Trim Seminar

APR 27 • Denver, CO

Sail Trim & Boat Speed

Learn about sail dynamics, sail trim, and optimizing performance for various wind conditions at this in-person seminar.

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APR 28 • Eugene, WA

Racing Strategy, Tactics & Rules

Learn techniques, tactics, and decision-making skills to help your performance on the race course at this in-person seminar

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APR 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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MAY 2024

Annapolis, MD

Compete in the Helly Hansen Sailing World Regatta with experienced coaches onboard high-performance J/80s.
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MAY 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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MAY 2024

Explore Croatia aboard Cataleya

A week-long cruise of Croatia onboard a fully crewed luxury yacht.
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MAY 2024

Amalfi Coast, Italy

Join this amazing flotilla and explore the beautiful coastline of Italy and enjoy the local cuisine and culture.
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MAY & JUN 2024

Dalmation Islands, Croatia

Embark on an unforgettable sailing journey tracing a course across Croatia's beautiful coastline.

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Jun 2024

Greece & The Aegean Sea

Sail with us on the Magical Aegean Sea, visit ancient ruins and old castles, and taste the real Greek Mediterranean diet.

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Jun 2024

Greece & The Ionian Sea

With its scenery, quaint towns, rich culture, hospitable people and ideal sailing conditions, this should be on every sailor’s bucket list!
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JUN 2024

Greece & The Saronic Gulf

Spirited sailing with ancient Greek history and you have the formula for a memorable flotilla vacation.
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Jun 2024

Victoria & the Gulf Islands

Join fellow sailors for a week cruising the beautiful San Juan and Canadian Gulf Islands to Victoria, BC.

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JUN 2024

British Virgin Islands, Caribbean

Find out why cruising sailors refer to the British Virgin Islands as a “sailor’s paradise.”

Lenny Shabes Sailing Festival

JUN 2024

Lenny Shabes Sailing Festival

Pay tribute to Lenny and join us in the Caribbean for a week of sailing festivities including sundowners, beach bonfires & regattas.

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JUN 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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JUN 2024

Greece

Experience Greece's Corfu Islands through sailing, cultural immersion, and personalized bareboat chartering.

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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 2024

Gastro-Sail, Croatia

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

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SEP 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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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

Islands of Belize

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