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.
Greek Island Hopper A Guided Flotilla
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.
Islands of Belize, Central America A Guided Flotilla
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!
MALLORCA A GUIDED FLOTILLA
Sailing the coastline of Mallorca is a dreamlike journey through the heart of the Mediterranean. As the largest of Spain’s Balearic Islands, Mallorca offers an irresistible blend of rugged coastlines, serene turquoise coves, charming seaside villages, and rich Spanish culture. The island is a sailor’s paradise—calm waters, steady breezes, and countless hidden anchorages create the perfect conditions for a relaxed and unforgettable voyage. Whether you’re exploring remote natural parks, enjoying a beachside paella, or sipping wine beneath the stars, Mallorca invites you to experience sailing at its most beautiful.
Amalfi Coast A GUIDED FLOTILLA
Set your course for a week of Italian magic on the Amalfi Coast Flotilla. This unforgettable journey blends world-class sailing with iconic stops in Capri, Positano, and Procida. Enjoy crystal-clear waters, gourmet cuisine, and sun-soaked coastlines aboard a luxurious catamaran, all with the perfect balance of freedom and expert support. Limited to just three boats, this is small-group adventure at its finest. Reserve your cabin today and sail Italy like never before.
San Juan Islands A GUIDED FLOTILLA
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.
The Ultimate Sailing Festival in the British Virgin Islands
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
Athens & the Saronic Gulf, Greece A Guided Flotilla
Set sail from Athens on a 7-night flotilla through the stunning Saronic Gulf. Cruise turquoise waters, explore charming island harbors, and swim in secluded coves while enjoying the perfect balance of independence and expert guidance. Skipper your own yacht or join by cabin aboard a fully equipped monohull or catamaran. With daily briefings, on-water support, and unforgettable Greek sunsets, this adventure blends hands-on sailing, culture, cuisine, and community.
Gulf of Fethiye, Turkey A Guided Flotilla
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.
Discover la paz, Mexico A GUIDED FLOTILLA
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.
Eclipse on the Med, Mallorca, Spain A Guided Flotilla
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
Spring Into The Bahamas A Guided Flotilla
Spring Into The Bahamas with Whitecaps Sailing and experience the beauty of the Abacos with expert leadership and camaraderie. Sail aboard spacious catamarans, explore charming island towns, snorkel vibrant reefs, and relax on pristine beaches — all while gaining hands-on sailing experience in calm, steady trade winds. With daily briefings, social events, and the guidance of Capt. Jean, Admiral Mila, and Capt. Joe, this flotilla blends adventure, community, and the magic of the Bahamas into an unforgettable sailing journey.
Sail The Bahamas A Guided Flotilla
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.
Catalina Island A Guided Flotilla
4 days / 3 nights sailing from Marina del Rey to Catalina Island with stops in Avalon and Two Harbors. Enjoy a welcome dinner, beach yoga, hiking, paddleboarding, dinghy raft-ups, happy hours, and fully supported flotilla sailing with Naos Yachts’ newest fleet.
Food & Wine in Dubrovnik, Croatia A Guided Flotilla
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.
Central Dalmatian Islands, Croatia A Guided Flotilla
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.















