Top Tortola Sailing Tours

Paddle through the mangrove forests of Beef Island on a stand-up paddleboard or kayak on a 1.5-hour excursion from Road Town. Known as the 'nurseries of the sea', these mangrove forests are a safe haven for juvenile marine life just learning to fend for themselves. Travel at a leisurely pace with your small group and local adventure guide, keeping an eye out for barracuda, baby sharks, stingrays and turtles. Use of all equipment is provided.

Discover BVI’s legendary Anne Bonny—a classic 60ft sailing yacht with pirate soul! Snorkel the iconic Caves & party at The Willy T floating bar. All-inclusive: gear, open bar (mimosas, rum punch), fresh lunch. Expert crew tailors every Thursday’s shared adventure to weather & guest vibes. Intimate groups, flexible fun—perfect for couples, friend groups & solos (12+). Book now & live the BVI dream! ⛵

Discover The Baths’ legendary granite boulders, hidden pools, and the famous Cathedral as your guide leads you through one of the Caribbean’s most breathtaking natural wonders. After your guided exploration and snorkeling in crystal-clear water, continue to Cooper Island or Peter Island for swimming, relaxing, or enjoying lunch at a stylish beachfront restaurant (at your own expense). An unforgettable blend of adventure, beauty, and island-hopping.

Discover BVI’s legendary Anne Bonny—a classic 60ft sailing yacht with pirate soul! Snorkel iconic Caves & Indians, swim with turtles at Pirates Bight, party at Willy T floating bar. All-inclusive: gear, open bar (mimosas, rum punch), fresh lunch. Expert crew tailors every adventure to weather & guest vibes. Children welcome. Book now & live the BVI dream! ⛵

Why is it called Dead Chest Island? What really happened on Norman Island? Who was Jost Van Dyke, and why is half the archipelago named after him? A self-guided tour on your phone, built specifically for people discovering these stories by boat, not by tour bus: bareboat, crewed, sailing or power. Every anchorage in the BVI is hiding a story — a wreck, a smuggler, a legend nobody's quite sure is true. Download before you leave home and each stop comes to life exactly when you get there, in whatever order your charter takes you — narrated in audio by our friendly pirate guide, or read at your own pace in text. It runs fully offline, however far you are from a signal. Along the way: a 50-question BVI quiz to settle who actually knows their history, and a digital treasure hunt played out across the islands. Snap photo and video challenges as you go, and we'll email the crew's memories back as a digital album.