Few places let you sail through living history like the British Virgin Islands. Moreover, with steady winds, calm seas, and 60+ islands, BVI sailing history is tied to its geography. Additionally, early mariners used sheltered anchorages and short hops, shaping the Caribbean’s top sailing destination.
So, plan your British Virgin Islands yacht charter today with BVISAIL and sail into history.
Modern BVI sailing history began in 1969 when Charlie and Ginny Cary founded The Moorings in Road Town with six yachts. They introduce bareboating to the Caribbean. For the first time, private sailors could captain their own vessels, transforming the BVI into a thriving charter hub.
The industry’s greatest test came in 2017 with Hurricane Irma. Recovery brought stronger marinas and modern fleets, cementing the BVI as the Caribbean’s sailing leader.
Decades after the first bareboat set sail, the BVI continues to outpace other destinations. Moreover, it’s not just the history; it’s the evolution of the experience.
If you want to walk (or sail) through history, these classic BVI sailing routes are a must:
Begin in Road Town, the birthplace of bareboating in 1969. Board your yacht and sail at sunset to The Bight, Norman Island.
Afterward, dive into pirate lore at Norman Island. Snorkel The Caves, rumored to hide treasure. Then, head to the legendary Willy T floating bar for a lively Caribbean lunch.
Explore history beneath the waves with a dive on the RMS Rhone, a mail ship lost in 1867. Then, end the day at Cooper Island, where a premier rum bar awaits.
Walk through the dramatic granite boulders of The Baths, one of the BVI’s geological wonders. Later, in the afternoon, sail north through the channel toward the famous North Sound, a landmark in BVI sailing history.
Begin by spending a full day in the sailor’s sanctuary of the North Sound. Then hop between Saba Rock and the Bitter End Yacht Club, soaking up the social heart of the BVI sailing scene.
Sail 15 miles across open blue water to Anegada, a coral atoll unlike any other in the BVI. Rent a “Moke” to explore flamingo ponds, then indulge in the island’s legendary lobster dinner.
First, anchor in White Bay and swim ashore to the Soggy Dollar Bar for the original Painkiller cocktail. Later, as night falls, join the festivities at Foxy’s, famous for live music and island traditions.
On your final day, stop at the colorful boutiques of Soper’s Hole in West End for souvenirs. Then enjoy a last reach back to Tortola, completing your full circle through the islands.
“A dream come true! Elise’s food was beyond incredible (those cookies!), and Max’s stop suggestions were perfect. Val’s warmth and care made us feel completely at home. Attention to detail from start to finish—unforgettable!”
The Sternchos Crew, Ocean Vibes, Dec 2025
Explore classic BVI sailing routes such as Tortola to Virgin Gorda. Discover Jost Van Dyke’s lively anchorages or the serene waters of Anegada. Whether it’s your first bareboat or a luxury crewed escape, BVISAIL connects you with top itineraries and vessels.
In 1969, The Moorings introduced bareboat charters in Road Town.
Bareboat or crewed: catamarans, sailing yachts, power yachts, and monohulls.
December to April offers the best winds and sailing conditions.
Fly into Beef Island (EIS) or connect via St. Thomas ferries.
Yes — short island hops and calm waters make it beginner‑friendly.
Contact us at 1-321-777-1707 or complete this form to discuss your vacation plans.
