Tortola’s calm waters and steady trade winds make it a prime location for sailing. Unlike some Caribbean islands that rely on motorboats and large tourist fleets, Tortola’s sailing excursions often feature authentic, relaxed experiences that focus on the scenery, the marine life, and the fun of being on the water. Whether you’re a seasoned sailor or just want a taste of the high seas, there’s an option for you. We’re particularly fond of the Norman Island – The Indians & The Caves Sailing & Snorkel Tour for its vibrant reefs and family-friendly vibe, and the Jost Van Dyke – Sandy Spit & Soggy Dollar Sailing Tour for its lively beach stops and iconic bar visits.
These tours highlight the natural beauty and laid-back fun that make sailing in Tortola special. From snorkeling in colorful coral reefs, exploring caves, or sipping a Painkiller at Soggy Dollar Bar, each offers a unique way to experience the islands’ charm. Choosing the right excursion depends on your interests—whether you want a calm day on the water with family or a lively party with friends. Let’s look at some of the top options.
1. Norman Island – The Indians & The Caves Sailing & Snorkel Tour
At number 1 on our list, this Norman Island snorkeling tour is hard to beat for its mix of calm sailing, excellent snorkeling, and family-friendly stops. Starting with Norman Island, which is known as the ‘Pirate’s Paradise’, the tour visits the famous Caves and the Indians, both teeming with marine life. The highlight is the chance to snorkel amid vibrant coral and schools of fish, with the crew often sailing twice in a day for extra time at each site. The boat is casual but safe, and the crew’s enthusiasm shines, especially if you’re lucky enough to see octopuses or turtles.
Guests consistently praise the crew, with reviews like “best snorkeling of our cruise,” and describe the experience as “breathtaking” and “perfect for kids and adults alike.” The tour lasts about 5 hours and is priced at $198 per person, offering great value for all the underwater sights and lively atmosphere. Plus, the boat’s relaxed pace and plentiful drinks make for a fun, social day. It’s ideal for first-timers, families, and anyone hoping to combine snorkeling with scenic sailing.
Bottom line: Expect a well-organized, lively trip that balances calm seas with excellent snorkeling and a friendly crew. Perfect for those wanting an all-around fun day on the water.
2. Jost Van Dyke – Sandy Spit & Soggy Dollar Sailing Tour in the BVI
Number 2 features the Jost Van Dyke – Sandy Spit & Soggy Dollar Sailing Tour, which is perfect for those who want a mix of beautiful beaches and lively beach bars. This 6-hour trip sails to some of the most Instagram-worthy spots: Sandy Spit, with its tiny, picture-perfect island, and White Bay’s famous Soggy Dollar Bar. The tour includes stops for swimming and relaxing on beaches with powdery sand and clear water. While snorkeling gear is provided, the area is known more for its sandy bottom and beach lounging than reef snorkeling.
The crew—Maddie and James—receive rave reviews for their personable, flexible approach, adjusting plans to fit weather and guest preferences. “A near-perfect day,” one reviewer called it, citing good drinks, fab weather, and stunning beaches. For $228, you get an engaging day visiting iconic spots, with plenty of time to unwind and soak up the vibe. This trip suits travelers looking for a lively, social experience with a chance to sip cocktails on the beach.
Bottom line: A fun, energetic outing combining beach lounging and bar hopping, ideal for groups wanting a party atmosphere with memorable stops.
3. Norman Island – The Caves & The Indians – Sailing & Snorkel Tour
This Norman Island snorkeling tour is similar to the number 1 but slightly longer and with a focus on family appeal. The 6.5-hour trip emphasizes calm sailing, with a full visit to the Caves and Indians, plus additional snorkeling spots and a scenic route around the island. The crew, praised for their attentiveness, shares insights into the area’s pirate lore and marine ecology, making it engaging for kids and adults alike.
Guests note the trip’s relaxed, safe, and well-paced nature, with activities designed to maximize underwater time. The tour is well-suited for families, with reviews like “great trip for families,” highlighting the excellent snorkeling spots and friendly staff. The price is $208 per person, which covers the full day of fun and exploration. The tour excels in providing a comfortable, educational experience that combines snorkeling, sailing, and island exploration.
Bottom line: Perfect for families and those new to sailing, this trip offers a comprehensive look at Norman Island’s best spots with a relaxed vibe.
4. Jost Van Dyke – Soggy Dollar & Sandy Spit Sailing Tour in the BVI
At number 4, this Jost Van Dyke — Soggy Dollar & Sandy Spit tour offers a full 6.5 hours of relaxation and fun. It’s aimed at travelers who want to indulge in the classic Jost Van Dyke experience—hopping between pristine beaches and enjoying the lively, open-air Soggy Dollar Bar. While snorkeling gear is available, the tour’s focus is more on sunbathing and drinks, with visits to the famous bar and the iconic Sandy Spit.
The crew’s professionalism and humor, as described by reviewers, make this a lively, memorable day. “Excellent boat, everything available,” one review states, emphasizing the seamless experience. The trip costs $208 per person, which is quite reasonable considering the iconic spots visited. It’s perfect for those seeking a laid-back, social day with lots of photo opportunities and a taste of Jost Van Dyke’s famous hospitality.
Bottom line: An easygoing, fun day with a focus on beach bars and iconic stops, great for travelers who want a mix of relaxation and lively atmosphere.
5. Sailing and Snorkeling to Norman Island and Caves
This sailing and snorkeling tour offers a full day of exploring Norman Island’s top underwater sites. Priced at $2,595 for up to 12 people, this private group experience is ideal for those looking for an exclusive, customizable day on the water. The itinerary includes stops at the Caves, the Indians (weather permitting), and Pirates Bight, with optional visits to Angelfish Reef or Kelly’s Cove.
The highlight here is the chance to see some of the best snorkeling in the BVI, with impressive underwater gardens and diverse marine life. It’s suited for groups seeking a more personal, flexible experience—families, friends, and couples who want to tailor their day. The trip’s longer duration and private nature make it a premium choice, emphasizing comfort, privacy, and customization.
Bottom line: Excellent for groups wanting an intimate, tailored adventure with prime snorkeling sites, at a higher price point.
6. Anne Bonny Shared Group Daysail – BVI’s Premier Sailing Adventure
The Anne Bonny shared daysail offers an authentic sailing experience aboard a 60-foot vessel with a pirate-inspired spirit. Priced at $195 per person, the trip includes snorkeling at the Caves and Indians, swimming with turtles at Pirates Bight, and enjoying drinks like mimosas and rum punches with a fresh lunch. The crew tailors the experience based on weather and group vibe, making each trip unique.
Though it has no reviews yet, the intimate group size and all-inclusive approach make it appealing for travelers who want a laid-back, social atmosphere. It’s best suited for couples, friends, or solo travelers who enjoy a bit of adventure and camaraderie. The flexible schedule and all-inclusive drinks and food add to its value.
Bottom line: Great for those who want a relaxed, social, all-inclusive sailing day with a touch of pirate spirit.
$195.00 per person
7. Private Tour Luxury Catamaran, Sail, Beach, Snorkel
For travelers seeking exclusivity, the Private Luxury Catamaran is the ultimate choice. Spanning 8 hours, the tour offers personalized itineraries around St. Thomas, Buck Island, and Water Island. It’s designed for small groups and includes swimming, snorkeling, and exploring at your own pace. The luxury aspect means comfort, excellent service, and flexibility—perfect for special occasions or those who want a tailored experience.
This tour will typically start with a hotel pickup, then cruise through stunning scenery, with drop-off options for exploring land or relaxing on the boat. The price is $1,511.97 per person, reflecting its premium status. Reviewers who value privacy and customization will find this ideal, as the crew can adapt the day to your preferences.
Bottom line: Best suited for travelers who want a private, high-end experience with complete control over the day’s activities.
$1,511.97 per person
How to Choose Your Perfect Sailing Experience in Tortola
Picking the right sailing trip depends on your budget, interests, and group size. If you’re traveling with family or want a comprehensive snorkeling adventure, the Norman Island – The Indians & The Caves offers a balanced mix. For a lively, social day with beach bars and sand, the Jost Van Dyke trips are perfect.
If privacy and tailoring are your priorities, consider the private luxury catamaran, while those on a budget or seeking group camaraderie will enjoy the Anne Bonny or Sailing and Snorkeling Norman Island trips. Booking early, especially in peak season, ensures you get your preferred date and experience.
Final Thoughts
Tortola offers a rich range of sailing experiences, from family-friendly snorkel trips to lively beach bar cruises, and luxe private charters. For an all-around great time, the Norman Island snorkeling tour stands out for its mix of fun and value, while the Jost Van Dyke bar-hopping trips are perfect for those looking for a party. If privacy and customization are your thing, splurge on a private luxury charter.
No matter your style, a sailing adventure in Tortola is bound to be memorable. Book early, pack your sense of adventure, and enjoy the stunning scenery that makes these waters so special.