Experience

FLOTILLAS

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

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. 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.

Islands of Belize, Central America A Guided Flotilla

Belize Sailing Vacations
Availability : Jun - Dec 2024

Explore Belize’s paradise islands on your own private luxury catamaran. Learn sailing from ASA certified instructors & crew. Snorkel, kayak, and fish in crystal clear waters. Enjoy gourmet meals & exotic drinks prepared by your crew. Experience a different destination every day on this ultimate sailing vacation!

From$2,995
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Turkey, Mediterranean A Guided Flotilla

Whitecaps Sailing School
Availability : September 21-28, 2024

Spirited sailing in the Gulf of Fethiye, turquoise waters that invite you for an invigorating swim, secluded anchorages to spend the night, small restaurants where you will be spoiled with amazing gastronomy. All this will make for an unforgettable flotilla experience.

From$2,095
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The Bahamas, Caribbean A Guided Flotilla

Whitecaps Sailing School
Availability : Dec 7-14, 2024

Join Whitecaps Sailing School in the Bahamas for an extraordinary sailing adventure. Explore turquoise waters, encounter dolphins, reefs, and sea turtles, all guided by expert ASA instructors.

From$2,300
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British Virgin Islands, Caribbean A Guided Flotilla

Annapolis Sailing School
Availability : Jan 31-Feb 7 & Feb 8-Feb 15

Join our vibrant flotilla for an unforgettable voyage through the BVI’s azure waters. Enjoy daily sailing excursions, island hopping, and leisurely activities like snorkeling and beachcombing. Whether you’re a seasoned sailor or a novice, this trip promises endless fun and relaxation in paradise.

From$2,450
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British Virgin Islands, Caribbean A Guided Flotilla

SailNashville
Availability : Feb 22 - Mar 01

The BVIs are the perfect destination for your first charter experience. A flotilla gives you the support group that makes that first charter experience even easier. And the weather in late February in the BVIs is some of the best.

From$2,500
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Paraty in Brazil, South America A Guided Flotilla

Whitecaps Sailing School
Availability : April 5-12, 2025

Brazil is one of the most popular destinations on many tourists’ bucket list, but still widely unknown for its sailing culture. Join us as we set sail on an amazing flotilla from Paraty.

From$2,190
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DISCOVER LA PAZ A GUIDED FLOTILLA

Go Baja Sailing
Availability : April 2025

Sailing the waters around La Paz, Mexico, is a truly magical experience. Nestled in the Sea of Cortez, often referred to as the “Aquarium of the World,” La Paz offers crystal-clear turquoise waters, calm seas, and stunning, unspoiled islands just offshore. With no Pacific ground swell, the waters are as smooth as a lake, making for relaxed and enjoyable sailing conditions.

From$1,998
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Ionian Sea, Greece A Guided Flotilla

Whitecaps Sailing
Availability : May & July 2025

The Ionian Sea offers crystal-clear waters and breathtaking landscapes, and our flotilla combines the thrill of sailing with camaraderie, mythical legends, ancient history, and legendary Greek hospitality.

From$2,195
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Amalfi Coast, Italy A Guided Flotilla

Whitecaps Sailing
Availability : June 2025

An unforgettable sailing adventure that blends stunning landscapes, cultural immersion, and camaraderie. Sail through the picturesque waters visiting hidden gems like Procida, Capri, and Positano, while enjoying the freedom of life at sea.

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2025

Lenny Shabes Sailing Festival ~ BVIs A Guided Flotilla

American Sailing
Availability : June 15-21, 2025

Join us for a week of sailing in paradise, as our late founder Lenny Shabes, set out to teach aspiring sailors to do. To pay tribute to all Lenny has done for the world of sailing, we are calling all sailors to partake in a week of festivities ranging from sundowners to regattas in the beautiful BVI’s.

From$2,499
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Gulf Islands, British Columbia A Guided Flotilla

San Juan Sailing
Availability : Jun 21 - 27, 2025

Join fellow sailors in cruising the charming east coast of Vancouver Island and the beautiful Gulf Islands. These islands boast sheltered waters, magnificent marine parks, quiet villages and welcoming marinas. Wildlife abounds on the land and in the sea, with deer, bald eagles, sea otters, seals, sea lions and orca whales commonplace.

From$1,700
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Central Dalmatian Islands, Croatia A Guided Flotilla

Whitecaps Sailing
Availability : August / September 2025

An unforgettable sailing adventure as we explore the stunning islands of Hvar, Vis, and other hidden gems along Croatia’s pristine coastline. Whether you’re an experienced sailor or a newcomer, this journey offers a perfect blend of beautiful sailing conditions, historic towns, and vibrant local culture.

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