The protected waters around St. John offer some of the Caribbean’s finest sailing. The island’s north shore delivers calm conditions perfect for day trips, while the south shore attracts more experienced sailors seeking adventure.
Crystal-clear visibility and steady trade winds make this a sailor’s paradise year-round.
Among the island’s best sailing options: The Full Day Cruz Bay excursion stands out for its expert crew and roomy deck space, while the Island Catamaran Cruise earns praise for its well-planned snorkeling stops and top-notch lunch service.
For those wanting privacy, the Private Full-Day Charter provides customized routes and personal attention.
Our tested favorite: the 2-Hour Sailing and Snorkeling Tour – perfect for first-timers and families, combining just enough time on water with excellent marine life viewing.
Let’s explore the top sailing tours St. John has to offer.
Key Points
- Full Day Cruz Bay by Sailboat offers an all-inclusive, highly-rated day sail experience with modern amenities and a personalized itinerary.
- St John Island Catamaran Cruise provides a 5-star rated excursion to explore the vibrant marine life around St. John.
- St John Private Full-Day Yacht Charter offers luxury yacht accommodations with extensive amenities and a hassle-free 5-star experience.
- 2 Hour Sailing and Snorkeling Tour on 60′ Sailboat showcases St. John’s natural beauty through a private sailing and snorkeling tour.
- Private Full-Day (6hr) Sailing and Snorkeling Tour by Island Sailing Tours provides a longer excursion with mixed reviews regarding crew professionalism and boat condition.
Full Day Cruz Bay by Sailboat – St John
The Full Day Cruz Bay by Sailboat – St John is an all-inclusive day sail that allows visitors to experience the stunning Virgin Islands from the water.
With a remarkable 98% of travelers recommending the tour and a Badge of Excellence, this sailing adventure is a must for those seeking a relaxing and comprehensive way to explore the region.
The tour includes a modern sailboat with hot water and restroom, providing a comfortable and convenient experience. Guests can enjoy a delicious lunch, an open bar with alcoholic beverages, snacks, and complimentary snorkeling equipment.
The fully flexible tour is tailored to the interests of the private group, ensuring a personalized and memorable adventure.
The tour departs from Cruz Bay, St John, and ends back at the same location. Pickup options are available, and the experience starts at 9:00 am.
With free cancellation up to 24 hours in advance and a lowest price guarantee, this sailing tour offers exceptional value and flexibility.
Read our full review: Full Day Cruz Bay by Sailboat – St John Review
Book now: Check availability
St John Island Catamaran Cruise
On a typical day, guests embark on the St John Island Catamaran Cruise aboard the sleek and modern Ocean Obsession: 32 World Cat, which can comfortably accommodate up to 12 people.
This 5-star rated tour departs from the Low Key Watersports store in Cruz Bay and takes adventurers on a journey to explore the stunning waters around St. John.
Throughout the experience, guests enjoy a variety of refreshments, including alcoholic beverages, soda, and bottled water, as well as a delicious lunch.
The tour also provides snorkeling equipment, allowing guests to dive below the surface and witness the vibrant marine life.
With a 100% recommendation rate from previous travelers, the St John Island Catamaran Cruise is an ideal choice for those seeking an unforgettable day of sailing and exploration in the US Virgin Islands.
The tour’s convenient location and private nature ensure a personalized and memorable experience for all participants.
Read our full review: St John Island Catamaran Cruise Review
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St John Private Full-Day Yacht Charter
For those seeking a more exclusive and personalized sailing experience in the stunning waters around St. John, the Grateful Ted: 60 Sunseeker offers a private full-day yacht charter.
This luxury vessel can accommodate up to 12 guests, providing ample space for groups to relax and enjoy the Caribbean sun and scenery.
The charter includes an impressive array of amenities, such as coffee, tea, brunch, snacks, alcoholic beverages, soda, bottled water, and lunch. Guests can also take advantage of the provided snorkeling equipment and air-conditioned comfort.
With a restroom on board and a 20% automatic gratuity, the Grateful Ted ensures a hassle-free and enjoyable experience.
The charter departs from the Low Key Watersports store in Cruz Bay at 8:30 AM and returns to the same location.
Booking and cancellation policies are flexible, with a confirmation received at the time of booking and free cancellation up to 24 hours before the experience.
With a perfect 5-star rating across multiple review platforms, the Grateful Ted provides an exceptional private yacht charter in St. John.
Read our full review: St John Private Full-Day Yacht Charter Review
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2 Hour Sailing and Snorkeling Tour on 60′ Sailboat From Cruz Bay, St. John
Adventurous travelers flock to the 2-Hour Sailing and Snorkeling Tour on a 60′ sailboat from Cruz Bay, St. John. This private tour offers a chance to experience the island’s stunning natural beauty from the water.
The sailboat departs from the Cruz Bay Ferry Dock, with alternative meeting points available at the Virgin Islands National Park Dock or Dinghy Dock.
The tour includes a range of inclusions, such as alcoholic beverages for those 18 and over, coffee, tea, snacks, and soda. Snorkeling equipment is also provided, allowing guests to explore the vibrant marine life beneath the surface.
With a total review count of 2 and an overall rating of 4.0/5, the tour has received positive feedback, praising the professionalism and informative sailing experience provided by Captain Sequoia and crew member Gary.
While the tour isn’t recommended for travelers with certain medical conditions, it’s suitable for those with a moderate level of physical fitness. The activity ends at the same meeting point, ensuring a seamless experience.
Read our full review: 2 Hour Sailing and Snorkeling Tour on 60′ Sailboat From Cruz Bay, St. John Review
Book now: Check availability
Private Full-Day (6hr) Sailing and Snorkeling Tour From Cruz Bay
Travelers seeking a more immersive sailing experience in St. John may consider the Private Full-Day (6hr) Sailing and Snorkeling Tour from Cruz Bay. Operated by Island Sailing Tours, this tour offers a lengthy six-hour excursion on a private sailboat.
The tour includes lunch, coffee/tea, alcoholic beverages, and use of snorkeling equipment.
However, the tour has received mixed feedback, with a single review indicating dissatisfaction with the crew’s professionalism and the boat’s condition. The host has emphasized their commitment to safety and guest satisfaction, stating that most guests have positive experiences.
It’s important to note that the tour isn’t recommended for travelers with certain medical conditions or physical limitations.
Plus, due to the lack of docks in Cruz Bay, all charter boats use smaller boats or dinghies for guest transport.
Prospective travelers should carefully consider the tour’s pros and cons before booking to ensure it aligns with their expectations and physical abilities.
Read our full review: Private Full-Day (6hr) Sailing and Snorkeling Tour From Cruz Bay Review
Book now: Check availability
The Sum Up
The Virgin Islands offer a variety of sailing experiences for visitors to St. John. From full-day cruises to private yacht charters, there’s something for every budget and interest level. Whether you’re looking to relax on the water, explore the island’s stunning coastline, or try your hand at snorkeling, these sailing tours provide an unforgettable way to experience the beauty of St. John.