Top Tortola Sailing Tours

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! ⛵

The only guide to the BVI written specifically for people exploring by boat — sailing charter, bareboat or powerboat. As you move between anchorages, the stories come to you. Led by the Jolly Pirate in audio, or read at your own pace, Pirates & Ports brings every stop to life — the history, legends, culture and characters that made these islands what they are. Why is it called Dead Chest Island? What really happened at Norman Island? Who was Jost Van Dyke? Works in any order, at any pace, on any itinerary. Download before you leave the dock, and it works offline throughout your charter. One purchase. One price. Your whole boat.

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 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! Our Wednesday shared group land and sea adventure explores the fabulous Island of Jost Van Dyke. Beginning with a leisurely cruise to Little Jost our first stop is at Diamond Reef where you can swim/snorkel and explore before lunch onboard at our second stop Great Harbour on the main Island of Jost Van Dyke. After lunch you will be delivered to shore where a land Safari will take you to White Bay and a quick stop at the iconic Soggy Dollar Bar. All-inclusive: snorkel gear, open bar (mimosas, rum punch), fresh lunch, safari bus. Our expert crew tailors every Wednesday'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 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! ⛵