FLOTILLAS

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.

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!

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.

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.

Join SailNashville’s BVI Flotilla in December 2025 for eight unforgettable days of sailing, island-hopping, and adventure in paradise. Learn new skills, make new friends, and create lifelong memories on crystal-clear Caribbean waters. Reserve your berth today!

Experience 6 days and 6 nights of unforgettable sailing through the breathtaking British Virgin Islands on our professionally led flotilla—where island-hopping adventure meets laid-back Caribbean charm. Perfect for both seasoned sailors and first-time cruisers, you’ll enjoy hands-on sailing by day and relaxed evenings with a fun, supportive group of fellow travelers.

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.

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.

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.

Set sail with Sail Nashville’s British Virgin Islands Flotilla for eight days and seven nights of unforgettable Caribbean adventure. Led by Captain John Summers and ASA-certified instructor Hayden Summers, you’ll explore Tortola, Norman Island, Cooper Island, Virgin Gorda, Anegada, Cane Garden Bay, and Jost Van Dyke. Choose a comfortable monohull or spacious catamaran, enjoy hands-on sailing, pristine beaches, and vibrant island culture, and create lasting memories with fellow adventurers in one of the world’s best sailing destinations.

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!

Set sail on an unforgettable 10-day adventure through the breathtaking waters of Thailand’s southern coast. This flotilla, hosted by Capt. Casey along with seasoned leaders Jean and Mila of Whitecaps Sailing, will take you through emerald lagoons, dramatic limestone karsts, and white-sand beaches in iconic locations like Phang Nga Bay, James Bond Island, Krabi, the Phi Phi Islands, Maya Bay, and Koh Yao Yai. You’ll sail aboard spacious, air-conditioned catamarans.

Join the Ultimate Sailing Experience! Set sail with us in the stunning British Virgin Islands, whether you want your own boat or prefer to share with others. Certified ASA instructors will be on board, guiding you through ASA 103, 104, and 114 certifications (for an additional fee) as you explore one of the world’s best sailing destinations.

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 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.