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.

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.

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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.

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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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French Riviera, A Guided Flotilla

Whitecaps Sailing
Availability : May - June 2025

Join us for an unforgettable week as we sail through the stunning French Riviera! Departing from the picturesque Port Les Cogolin, you’ll explore iconic destinations like St. Tropez, the charming Bormes-les-Mimosas, and the beautiful islands of Porquerolles and Port-Cros.

From$2,395
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Corfu, Greece A Guided Flotilla

Fair Winds Sailing Greece
Availability : May 31 - Jun 07, 2025

Join Fair Winds Sailing Greece, a certified American Sailing Affiliate located on Corfu Island, Greece and sail with us the north Ionian Sea, one of the most popular and beautiful sailing destinations worldwide. Enjoy the incomparable beauty of the Greek islands, the unique deep blue color of our sea and the amazing Greek food.

From$1,995
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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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Athens, Greece A Guided Flotilla

Whitecaps Sailing
Availability : June 2025

Imagine a week exploring the pristine waters of the Saronic Gulf, setting sail from Athens alongside a community of adventurous, like-minded travelers. Discover hidden coves, swim in azure bays, and dock in charming Greek villages each evening, where local culture and cuisine await!

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Corfu, Greece A Guided Flotilla

Whitecaps Sailing
Availability : June / July 2025

If you have ever dreamed of cruising the Ionian Sea where Homer’s heroes once sailed, this flotilla offers an unforgettable experience. Set on Greece’s west coast, the northern Ionian itinerary combines the best of sailing, local camaraderie, ancient myths, and authentic Greek hospitality.

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Montenegro A Guided Flotilla

Whitecaps Sailing
Availability : June 2025

Imagine a week exploring the pristine waters of the Saronic Gulf, setting sail from Athens alongside a community of adventurous, like-minded travelers. Discover hidden coves, swim in azure bays, and dock in charming Greek villages each evening, where local culture and cuisine await!

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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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Gulf of Fethiye, Turkey A Guided Flotilla

Whitecaps Sailing
Availability : September 2025

From the vibrant history of Pashas and Whirling Dervishes to the breathtaking ruins of ancient Greek, Roman, and Ephesus cities, Turkey is a land where East meets West in perfect harmony. And now, you can sail its stunning Mediterranean waters with Med Sailing Adventures.

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Dubrovnik to Split, Croatia A Guided Flotilla

Whitecaps Sailing
Availability : September 2025

Join our Mile Builder Flotilla for a stunning one-way journey from Dubrovnik to Trogir near Split. Experience the charm of Ston, the natural beauty of Mljet National Park, and the rich history of Korčula before soaking up the vibrant atmosphere of Hvar. This adventure is perfect for building your sailing skills while exploring Croatia’s breathtaking coastline. Set sail with us for an unforgettable week of discovery and camaraderie on the water!

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