If you’re dreaming of learning to sail amid the sparkling waters of the U.S. Virgin Islands, this private sailing experience in St. John might just be your perfect match. For around $1,395 per group, up to six people, you’ll spend roughly five hours on the water, guided by a seasoned captain who makes the experience both educational and relaxing. Whether you’re eager to steer the boat yourself or prefer to kick back and soak up the scenery, this tour offers a flexible, all-inclusive way to enjoy the Caribbean’s best virtues: stunning views, wildlife sightings, snorkeling, and a touch of sailing expertise.
Two things we love about this trip? First, the personalized attention that a private tour offers, including tailored instruction if you want to learn or just relax and cruise. Second, the variety of activities, from sailing to snorkeling in calm protected waters, plus the all-day supply of food and drinks—deli sandwiches, snacks, mixed drinks, beer, and soda—that keep you fueled for adventure.
A possible consideration? The price might seem high, but when you factor in private guide service, all gear, drinks, and lunch, it’s a good deal for a full day of premium, hassle-free fun. This experience suits travelers who appreciate personalized service, want a mix of learning and leisure, and enjoy beautiful, quiet anchorages with wildlife and beaches that look almost untouched.
Key Points
- Private, all-inclusive experience tailored to your group’s interests and pace.
- Learn the basics of sailing or simply enjoy relaxing on the boat.
- Snorkeling gear included, with recommended snorkeling spots.
- Multiple stops for swimming, snorkeling, and beach time.
- Gourmet deli lunch and a full bar with cocktails, beer, and soft drinks.
- Flexible options: helm the boat yourself or let the captain take over.
A Closer Look at What to Expect
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Imagine spending a full day on a 40-foot sailboat in the calm waters of St. John’s protected western shoreline. The experience is expertly designed to maximize relaxation, enjoyment, and learning, whether you’re a sailing novice or someone who’s been on boats before. The starting point is the Cruz Bay Ferry Dock, conveniently accessible, with the tour kicking off at 10 a.m.—a perfect time to soak up the morning sun and catch the tranquility of the Caribbean.
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The Itinerary and Stops
Once onboard, your captain will guide you through the basics of sailing, offering instruction tailored to your group’s interests and skill levels. If you’re eager to try your hand at steering, you’ll be encouraged to take the helm. For those who prefer to relax, the captain provides guidance or simply steers while you enjoy the scenery.
The first stop offers a chance to snorkel in clear, protected waters. Snorkel gear is included, and your captain will recommend the best spots to observe local marine life. We loved hearing from guests that “Captain Mike tailored a great experience” and was “absolutely great with our daughter”, making the day both educational and fun for all ages.
After snorkeling and some swimming, you’ll enjoy complimentary snacks and drinks—from chips and granola to freshly mixed cocktails and cold beer—perfect for refueling. The boat then moves to a second stop, often a pristine shoreline or beach, where you’ll have more chances to swim, relax, or stroll on white sandy beaches.
If you’re feeling adventurous, you can continue sailing along the coast or simply enjoy basking in the sun, the gentle breeze, and the stunning views. The flexibility to helm the boat for more instruction or lean back and relax adds to the experience’s appeal.
Food, Drinks, and Gear
This tour’s all-inclusive nature is a huge plus. The gourmet deli lunch is hearty enough to keep you energized, and the full bar features craft cocktails (or mocktails if you prefer), sparkling wine, beer, soda, juice, and bottled water. Snorkeling equipment is provided, so you can focus on enjoying the vivid underwater life without worrying about gear.
Who Should Book?
This experience is perfect for families, couples, or small groups looking for a personalized, relaxed day with a mix of sailing, snorkeling, and beach time. Those interested in learning sailing basics or steering the boat will love the hands-on approach, while others may prefer to soak up the sun and scenery. The reviews highlight that the guides are knowledgeable and attentive, making it a memorable, stress-free outing.
Why This Tour Offers Good Value
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At nearly five hours, the tour is a substantial chunk of your day — especially considering it includes private guide service, all gear, food, drinks, and fuel. For about $230 per person (if split among six), it’s a fair deal for a luxury experience that combines adventure, relaxation, and learning. Unlike group tours, the private setting ensures personalized attention, and the full bar and gourmet lunch elevate the experience beyond typical boat trips.
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Authentic Experiences and Real Guests’ Perspectives
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Guests have raved about the expertise of the captain and how the day felt tailored to their interests. One reviewer noted, “Captain Mike tailored a great experience for us” and appreciated how he was “absolutely great with our daughter”, emphasizing the tour’s family-friendly vibe. This personal touch makes a significant difference, especially if you’re traveling with children or less confident swimmers.
The stunning views of the coastline, combined with the chance to observe local wildlife while snorkeling, make this a nature-lover’s favorite. The fact that snorkel gear is included and the captain’s recommendations are tailored to the conditions adds to the overall value.
Practical Tips for Booking
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- The tour starts at 10 a.m., so plan to arrive a little early at the Cruz Bay Ferry Dock.
- Since gratuities aren’t included, consider tipping if you feel the guide made your day special—most travelers do.
- Bring towels (not provided), sunscreen, sunglasses, and a hat for comfort.
- The trip is generally suitable for most travelers, including those with service animals.
- If weather conditions are poor, the tour can be rescheduled or refunded, but check the cancellation policy before booking.
Summary: Who Will Love This Experience?
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This Learn to Sail tour offers a fantastic blend of personalized instruction, sightseeing, snorkeling, and relaxation. It’s ideal for families wanting a safe, engaging activity, couples seeking a romantic day on the water, or small groups eager to learn a new skill while enjoying the Caribbean’s beauty. The all-inclusive nature—from food and drinks to gear—means no fuss, only fun.
If you’re looking for a high-quality, flexible day on the water with knowledgeable guides and stunning scenery, this trip hits the mark. It’s a value-rich experience that leaves you with lifelong memories and new skills.
Frequently Asked Questions
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Is transportation included?
Pickup is offered, but the main meeting point is the Cruz Bay Ferry Dock, making it easy to reach from most accommodations.
How long does the tour last?
Approximately five hours, starting at 10 a.m., with several stops for snorkeling and relaxing.
What should I bring?
Towels are not included, so bring your own. Sunscreen, sunglasses, a hat, and possibly a camera are good ideas.
Can I steer the boat myself?
Yes, you’re welcome to helm the boat if you want more hands-on instruction, or you can relax and leave it to the captain.
Are drinks and lunch included?
Yes, all food and drinks—gourmet deli lunch, cocktails, beer, soda, and water—are included.
Is snorkeling gear provided?
Yes, snorkeling equipment is included for your convenience.
What if the weather is bad?
The tour requires good weather, but if canceled due to weather conditions, you’ll be offered a different date or a full refund.
Who is the tour provider?
Morningstar Sailing and Power Charters.
In the end, this private sailing lesson in St. John offers an authentic Caribbean experience with the comforts of personalized service, beautiful scenery, and a good dose of adventure. Whether you want to learn the basics of sailing, snorkel in crystal-clear waters, or just relax with a cold drink on deck, it’s a day designed for memorable moments and new skills.