Top St John Sailing Trips

Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin St. John

Join us for a day of sailing and snorkeling aboard one of our luxury catamarans and enjoy a sun-filled day topped off with lunch at …More

Join us for a day of sailing and snorkeling aboard one of our luxury catamarans and enjoy a sun-filled day topped off with lunch at...

6 hours 30 minutes Free Cancellation
4.9 (349)
from
$149
St. John Days End Sunset Sail with Open Bar from the Westin

As the sun sets our sails rise, and the champagne flows. Experience a Caribbean sunset and celebrate one of nature’s wonders of color under full …More

As the sun sets our sails rise, and the champagne flows. Experience a Caribbean sunset and celebrate one of nature’s wonders of color under full...

1 hour 30 minutes Free Cancellation
4.8 (313)
from
$99
St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast - Westin

This one of a kind excursion to Jost Van Dyke allows passengers to spend the most time on the island out of all other group …More

This one of a kind excursion to Jost Van Dyke allows passengers to spend the most time on the island out of all other group...

8 hours Free Cancellation
4.9 (207)
from
$289
St. John PiZZA Pi Snorkel Sail with Beach Stop, Lunch & Open Bar - Westin

Join us aboard one of our luxury catamarans, as we set sail for the best snorkeling destinations surrounding St. John. Start the day with a …More

Join us aboard one of our luxury catamarans, as we set sail for the best snorkeling destinations surrounding St. John. Start the day with a...

5 hours Free Cancellation
4.9 (172)
from
$129
All Inclusive St. John Boating Adventure

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 Hotel pickup offered Free Cancellation
5.0 (79)
from
$314
Private Day Charter Classic Sailboat

To maximize your day and our destination options in the National Park, we offer flexible timing allowing for an easy transfer away from the busy …More

To maximize your day and our destination options in the National Park, we offer flexible timing allowing for an easy transfer away from the busy...

4 to 5 hours Hotel pickup offered Free Cancellation
5.0 (70)
from
$1,395
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
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
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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