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Top US Virgin Islands Sailing Trips

Group Sunset Sail St. John

We are a family owned small business; we have a love for true sailing and authentic relationships here in the islands. Looking for more time …More

We are a family owned small business; we have a love for true sailing and authentic relationships here in the islands. Looking for more time...

2 hours 30 minutes Free Cancellation
5.0 (32)
from
$245
National Park & Surrounding Cays Sunset Sail

Sail the beautiful and calm protected waters of the Virgin Islands National Park aboard your private and all inclusive sailboat. Full Day, all inclusive, private …More

Cruz Bay, US Virgin Islands

Sail the beautiful and calm protected waters of the Virgin Islands National Park aboard your private and all inclusive sailboat. Full Day, all inclusive, private...

2 to 3 hours Free Cancellation
5.0 (13)
from
$1,000
Discover the Best of St. John - Snorkel, Beach & Shopping!

Experience the best of two tropical islands! Sail to the island escape of St. John from St. Thomas aboard the beautiful Lady Lynsey. After snorkeling …More

Cruz Bay, US Virgin Islands

Experience the best of two tropical islands! Sail to the island escape of St. John from St. Thomas aboard the beautiful Lady Lynsey. After snorkeling...

5 hours Hotel pickup offered Free Cancellation
4.9 (7)
from
$129
SPECIAL - (Up to 4 Passengers) All Inclusive Day Sail

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful …More

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful...

5 hours
5.0 (3)
from
$1,347
St Thomas Pizza Pi Snorkel Sail From Frenchman's Reef

Start the day with a sail to an offshore cay for premier snorkeling. In addition to fruit, salads, and cookies, our main lunch will be …More

Start the day with a sail to an offshore cay for premier snorkeling. In addition to fruit, salads, and cookies, our main lunch will be...

5 hours Free Cancellation
5.0 (2)
from
$139
Learn to Sail - Sailing Lessons All Inclusive

With 20 years of experience sailing here in the US Virgin Islands we have found that our guests value the smaller venue for purists sailing. …More

With 20 years of experience sailing here in the US Virgin Islands we have found that our guests value the smaller venue for purists sailing....

5 hours
5.0 (4)
from
$1,395
SPECIAL - All Inclusive Day Sail

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful …More

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful...

5 hours
5.0 (1)
from
$1,550
Turtles Guaranteed! Fuel Price Included. Smooth, Comfortable Ride

We would love to host you all and show you a wonderful day on the water! This itinerary is set to maximize witnessing the beauty …More

We would love to host you all and show you a wonderful day on the water! This itinerary is set to maximize witnessing the beauty...

5 hours Free Cancellation
5.0 (1)
from
$1,300

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These answers are based on answers previously given to Cool Shore Excursions customers' questions.

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