Flotillas

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 […]

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.

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.

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 […]

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.

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.

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.

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.

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.

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!

Join a flotilla in Montenegro for an unforgettable sailing adventure! Experience breathtaking scenery in the stunning Bay of Kotor, explore charming coastal towns rich in culture, and enjoy a supportive community of fellow sailing enthusiasts.

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 […]

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.

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.

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 […]

Embark on the Unsalted Flotilla: Wherever the Wind Takes Us with Great Lakes Sailing Co.! Set sail on the stunning waters of Northern Michigan, explore charming harbor towns, and experience the freedom of flotilla sailing. With expert guidance, ASA certification options, and the camaraderie of fellow sailors, this adventure is perfect for both seasoned and […]