Caribbean

Belize’s sailing experience extends beyond the sea, offering captivating inland ventures. With BSV’s fully crewed catamarans, guests enjoy the ultimate all-inclusive charter, accessing the world’s largest living barrier reef and remote sites.

To pay tribute to our founder Lenny Shabes we are calling all sailors to join us for a week of sailing in the beautiful BVI’s to enjoy festivities ranging from sundowners to regattas.

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!

Embark on a transformative journey through the British Virgin Islands aboard Arabella with American Sailing. From the lively shores of Jost Van Dyke to the serene beauty of Virgin Gorda, every moment is promised to be infused with laughter, camaraderie, and pure joy. Lose yourself in the rhythm of island life, where each day brings new adventures and lifelong friendships. Your dream itinerary awaits – let Arabella be your guide through paradise.

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!

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!

Join Annapolis Sailing School for an unforgettable Learn-to-Sail Vacation in the British Virgin Islands from February 7–14 or February 15–21, 2026. Sail aboard a 45’+ catamaran or 48’ monohull while exploring Tortola, Virgin Gorda, Anegada, Jost Van Dyke, and more, with opportunities to earn ASA 104 Bareboat Cruising and ASA 114 Cruising Catamaran certifications. Enjoy hands-on training, stunning anchorages, and the perfect balance of learning, adventure, and Caribbean relaxation.

Experience the vibrant spirit of the Caribbean — from the historic harbors of Antigua and the pink sands of Barbuda to the glamorous shores of St. Barths. Sail through turquoise waters aboard the luxurious schooner RHEA, as we follow the exhilarating spectacle of the St. Barths Bucket Regatta. Bask in the steady trade winds, savor world-class hospitality, and witness the unmatched beauty of classic yacht racing in one of the world’s most breathtaking destinations.

Join American Sailing for an unforgettable 8-day adventure racing in the Antigua Classic Yacht Regatta aboard the luxury sailing yacht Chronos. Compete, cruise, and celebrate in the Caribbean’s most iconic regatta while enjoying world-class service, stunning beaches, and vibrant island culture.

Join American Sailing and Caribbean Sail Training for a hands-on racing adventure in the British Virgin Islands. Sail aboard Spirit of Juno, a Farr 65 performance yacht, and become part of the crew during one of the Caribbean’s most exciting regattas. Whether you’re new to racing or a seasoned sailor, you’ll learn, compete, and experience the thrill of teamwork at sea.

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.