British Virgin Islands

Embrace the adventure of a lifetime with our exclusive Learn to Sail vacation. Journey from Bermuda’s serene shores to the iconic Manhattan Marina, mastering the art of sailing and earning ASA credentials on the majestic Arabella. Don’t miss this unparalleled blend of education, adventure, and luxury at sea.

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!

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!

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.

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.

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. $3500 per person (double occupancy cabin with private head and shower).