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.

Discover la paz, Mexico A GUIDED FLOTILLA

Go Baja Sailing
Availability : Various Dates May 2026 - May 2027

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$2,250
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Gulf of Fethiye Turkey

Gulf of Fethiye, Turkey A Guided Flotilla

Whitecaps Sailing
Availability : Jun 06 - 13, 2026

Explore the breathtaking southwestern coast of Türkiye on a 7-night sailing flotilla through the stunning Bay of Fethiye. With crystal-clear waters, reliable Mediterranean winds, and secluded coves accessible only by sea, this region offers the perfect blend of relaxed cruising and spirited sailing. Each day brings ancient Lycian ruins, dramatic landscapes like Butterfly Valley, charming harbor towns such as Göcek, and unforgettable sunsets at anchor.

From$2,295
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San Juan Islands A GUIDED FLOTILLA

San Juan Sailing
Availability : Jun 19 - 26, 2026

Join fellow boaters in exploring the highlights of the San Juan Islands during the early summer. This flotilla is timed to beat the crowds and enjoy the long hours of daylight during the summer solstice. The San Juan Islands boast sheltered waters, magnificent marine parks, quaint villages and welcoming marinas. Wildlife abounds on the land and in the sea, with deer, bald eagles, otters, seals, sea lions and orca whales commonplace.

From$1,450
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Islands of Belize, Central America A Guided Flotilla

Belize Sailing Vacations
Availability : Various Dates May - Dec 2026

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$2,595
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The Ultimate Sailing Festival in the British Virgin Islands

American Sailing
Availability : Jun 21-27, 2026

Enjoy seven days and six nights of sailing alongside fellow boats for one epic flotilla experience. Explore the iconic baths, get in on a small boat regatta at the famous Bitter End Yacht Club, and swim to shore to visit the iconic Soggy Dollar Bar. It’s going to be an action-packed sailing adventure!

Sail a luxury catamaran, race in a Caribbean regatta, and party with sailors from around the world during a 7-day flotilla celebrating the legacy of Lenny Shabes.

  • British Virgin Islands
  • June 21–27, 2026
  • Luxury catamarans with skipper included
  • Sailing, regattas, raft-ups & dock parties

From$2,499
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Apostle Islands, Wisconsin A Guided Flotilla

Northern Breezes Sailing
Availability : July 09 - 12, 2026

Explore the stunning Apostle Islands National Lakeshore on this unforgettable flotilla with Northern Breezes Sailing. Often called the “BVI of the North,” this adventure features 22 islands, pristine anchorages, scenic hiking trails, and historic lighthouses maintained by the National Park Service. Sail the fresh waters of Lake Superior aboard well-maintained boats ranging from 33’ to 44’, with options for bareboat or captained charters.

From$995
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Eclipse on the Med, Mallorca, Spain A Guided Flotilla

Whitecaps Sailing
Availability : Aug 08 - 15, 2026

Experience the magic of a total solar eclipse as it unfolds above the waters of the Mediterranean—an awe-inspiring event witnessed from the deck of a sailing yacht off the coast of Mallorca. This once-in-a-lifetime adventure combines the wonder of the cosmos with the natural beauty, rich history, and coastal charm of one of Spain’s most stunning islands

From$3,150
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Food & Wine in Dubrovnik, Croatia A Guided Flotilla

Whitecaps Sailing
Availability : Aug 29 - Sep 05, 2026

Sail Croatia’s stunning Dalmatian Coast on a week-long GASTRO-SAIL Food & Wine Flotilla from Dubrovnik. Explore Korčula, Mljet, and Ston while visiting family-run wineries, oyster farms, and waterfront restaurants accessible only by boat. Swim in crystal-clear Adriatic waters, enjoy relaxed island sailing, and experience the rich flavors and culture of coastal Croatia alongside fellow food and wine lovers.

From$2,550
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central dalmatian islands

Central Dalmatian Islands, Croatia A Guided Flotilla

Whitecaps Sailing
Availability : Sep 12 - Sep 19, 2026

Sail Croatia’s Dalmatian Coast on a week-long flotilla through turquoise waters, historic towns, and island harbors. Departing from Trogir, this classic itinerary explores Vis, Hvar, and more with relaxed sailing, daily briefings, and the camaraderie of a welcoming sailing community.

From$2,525
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Greek Island Hopper A Guided Flotilla

Fair Winds Sailing Greece
Availability : Sep 27 - Oct 03, 2026

Set sail on the Greek Island Hopper Flotilla, hosted by Fair Winds Sailing Greece, and experience the beauty of Corfu and the surrounding Ionian islands. Guided by local captains, you’ll visit favorite anchorages, UNESCO World Heritage sites, and charming island towns while enjoying the perfect blend of sailing, culture, and relaxation. Sail aboard modern monohulls or catamarans, share meals and onshore excursions with fellow sailors, and discover Greece as seen through the eyes of those who know it best.

From$2,250
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Barcolana Regatta from Croatia to Italy A Guided Flotilla

Adriatic Sailing Academy
Availability : October 07 - 13, 2026

Sail the Adriatic on an unforgettable Croatia-to-Italy flotilla culminating in the legendary Barcolana Regatta in Trieste. Led by American Sailing certified instructor Fabio Matijević, this experience combines scenic coastal passages, historic ports, local culture, mini regatta training, and the excitement of racing alongside hundreds of sailors in one of the world’s largest sailing events. Perfect for both experienced and newer sailors, with bareboat, skippered, private, and certification options available.

From$2,600
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Sail The Bahamas A Guided Flotilla

Cruise Abaco
Availability : Nov 08 - 14, 2026

Join American Sailing Vacations and Cruise Abaco for a week of clear, warm waters, white-sand beaches, and unforgettable sailing through the Abacos. This flotilla offers the perfect mix of freedom and fun — explore the Out Islands by day and share sundowners with new friends each evening.

From$2,250
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