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Top St Thomas Sailing Trips

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St Thomas Tours

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Days End Sunset Sail with Open Bar from Frenchman's Reef

Step aboard our luxury sailing catamaran for a fun and relaxing sunset sail departing from Frenchman’s Reef. Take in a magnificent Caribbean sunset while under …More

4.6 (78)

Days End Sunset Sail with Open Bar from Frenchman's Reef

Step aboard our luxury sailing catamaran for a fun and relaxing sunset sail departing from Frenchman’s Reef. Take in a magnificent Caribbean sunset while under...

1 hour 30 minutes Free Cancellation
4.6 (78)
from
$89
Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

Come swim with the resident green sea turtles and tropical fish on this 3 hour snorkel & sail adventure in St. Thomas aboard The VI …More

4.8 (2,279)

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

Come swim with the resident green sea turtles and tropical fish on this 3 hour snorkel & sail adventure in St. Thomas aboard The VI...

3 hours Free Cancellation
4.8 (2,279)
from
$119
Days End Sunset Sail with Open Bar from St. Thomas Ritz-Carlton

Enjoy a relaxing and romantic sail in the calm waters of Pillsbury Sound with views of the beautiful beaches on the north shore of St. …More

4.7 (50)

Days End Sunset Sail with Open Bar from St. Thomas Ritz-Carlton

Enjoy a relaxing and romantic sail in the calm waters of Pillsbury Sound with views of the beautiful beaches on the north shore of St....

1 hour 30 minutes Free Cancellation
4.7 (50)
from
$129
St. Thomas Dinner Sail to Lovango with Open Bar

Step aboard our luxury 65 foot catamaran Lady Lynsey II for an evening escape to the private island of Lovango Cay for dinner under the …More

4.6 (43)

St. Thomas Dinner Sail to Lovango with Open Bar

Step aboard our luxury 65 foot catamaran Lady Lynsey II for an evening escape to the private island of Lovango Cay for dinner under the...

4 hours Free Cancellation
4.6 (43)
from
$129
Sail, Shop and Snorkel in St. John from Westin Frenchman's Reef

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

4.8 (29)

Sail, Shop and Snorkel in St. John from Westin Frenchman's Reef

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

7 hours Free Cancellation
4.8 (29)
from
$129
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
4.9 (7)

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...

5 hours Hotel pickup offered Free Cancellation
4.9 (7)
from
$129
All-Inclusive Sunset Sail - Semi Private - Only 6 Guests

An Unforgettable Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us …More

5.0 (103)

All-Inclusive Sunset Sail - Semi Private - Only 6 Guests

An Unforgettable Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us...

2 hours Free Cancellation
5.0 (103)
from
$139
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

5.0 (2)

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...

5 hours Free Cancellation
5.0 (2)
from
$139
Half Day Sail and Snorkel with the Turtles

Snorkel and Sail with the USCG Licensed Crew aboard the Sailing Yacht "FURY", a beautifully restored Morgan 46' Ketch. We actually "SAIL" out to the …More

Likely to Sell Out
Likely to Sell Out
4.9 (300)

Half Day Sail and Snorkel with the Turtles

Snorkel and Sail with the USCG Licensed Crew aboard the Sailing Yacht "FURY", a beautifully restored Morgan 46' Ketch. We actually "SAIL" out to the...

3 hours 30 minutes Free Cancellation
4.9 (300)
from
$149
St. Thomas Dinner Sail to St. John with Open Bar - Ritz-Carlton

Step aboard our luxury 53 foot catamaran for an evening escape to the island of St. John. This popular sail departs directly from The Ritz-Carlton …More

4.7 (56)

St. Thomas Dinner Sail to St. John with Open Bar - Ritz-Carlton

Step aboard our luxury 53 foot catamaran for an evening escape to the island of St. John. This popular sail departs directly from The Ritz-Carlton...

5 hours Free Cancellation
4.7 (56)
from
$149
Snorkel Cat All Inclusive Adventure

What makes our trip unique is the rare opportunity to snorkel at both the pristine waters of St. John’s National Park and a remote, uninhabited …More

4.9 (1,055)

Snorkel Cat All Inclusive Adventure

What makes our trip unique is the rare opportunity to snorkel at both the pristine waters of St. John’s National Park and a remote, uninhabited...

5 hours Free Cancellation
4.9 (1,055)
from
$150
Sail/Snorkel Adventure from Sapphire Marina,STT NO CROWDS~ 6 GUEST MAX

We offer a semi private setting with a maximum of 6 guest and a personalized experience. The sailboat Cosmos Mariner is stable, sea kindly, and …More

Likely to Sell Out
Likely to Sell Out
5.0 (257)

Sail/Snorkel Adventure from Sapphire Marina,STT NO CROWDS~ 6 GUEST MAX

We offer a semi private setting with a maximum of 6 guest and a personalized experience. The sailboat Cosmos Mariner is stable, sea kindly, and...

3 hours Free Cancellation
5.0 (257)
from
$159
St. Thomas Maho Bay Turtle Snorkel Sail - Ritz-Carlton

Sail away aboard Lady Lynsey II into the Virgin Island’s National Park to discover the wonders of snorkeling with sea turtles. …More

4.9 (61)

St. Thomas Maho Bay Turtle Snorkel Sail - Ritz-Carlton

Sail away aboard Lady Lynsey II into the Virgin Island’s National Park to discover the wonders of snorkeling with sea turtles....

5 hours Free Cancellation
4.9 (61)
from
$159
Half Day Private Sailing Catamaran and Snorkel Trip to St John

Sail with Liberty guests experience real sailing on our spacious, private catamaran. We sail you to the St John National Park for spectacular snorkeling and …More

Likely to Sell Out
Likely to Sell Out
5.0 (127)

Half Day Private Sailing Catamaran and Snorkel Trip to St John

Sail with Liberty guests experience real sailing on our spacious, private catamaran. We sail you to the St John National Park for spectacular snorkeling and...

3 hours 30 minutes Free Cancellation
5.0 (127)
from
$165
St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max

An Unforgettable Sailing Experience! We offer a Semi-private and all inclusive Day trip that will be the best day of your vacation. There is no …More

5.0 (700)

St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max

An Unforgettable Sailing Experience! We offer a Semi-private and all inclusive Day trip that will be the best day of your vacation. There is no...

6 hours 30 minutes Free Cancellation
5.0 (700)
from
$245
Amazing Half Day Private Boat Charter on Luxury Sailing Catamaran

Swim and snorkel beautiful reefs. See the amazing beaches and Islands while catching some sun on the bean bags on top of the trampolines. You …More

Likely to Sell Out
Likely to Sell Out
5.0 (12)

Amazing Half Day Private Boat Charter on Luxury Sailing Catamaran

Swim and snorkel beautiful reefs. See the amazing beaches and Islands while catching some sun on the bean bags on top of the trampolines. You...

4 hours 30 minutes Free Cancellation
5.0 (12)
from
$250
6-Hour Turtles, Pizza Pi & Sunset Sail

** This trip departs from St. Thomas Only ** Get ready for a day of sun, sea, and stories! Our crew members, who also call …More

Likely to Sell Out
Likely to Sell Out
5.0 (441)

6-Hour Turtles, Pizza Pi & Sunset Sail

** This trip departs from St. Thomas Only ** Get ready for a day of sun, sea, and stories! Our crew members, who also call...

6 hours
5.0 (441)
from
$280
Full Day Sail with Max Charters

A day with Max Charters is a unique way to experience the Virgin Islands. We carry fewer passengers than most charter companies in order to …More

Likely to Sell Out
Likely to Sell Out
5.0 (136)

Full Day Sail with Max Charters

A day with Max Charters is a unique way to experience the Virgin Islands. We carry fewer passengers than most charter companies in order to...

6 hours Free Cancellation
5.0 (136)
from
$285
Full-Day Sailing Tour in Virgin Islands National Park

Set sail and explore the Virgin Islands National Park! Enjoy a day of sailing and snorkeling with lunch and drinks provided! Where to meet: We …More

Likely to Sell Out
Likely to Sell Out
4.9 (49)

Full-Day Sailing Tour in Virgin Islands National Park

Set sail and explore the Virgin Islands National Park! Enjoy a day of sailing and snorkeling with lunch and drinks provided! Where to meet: We...

6 hours Free Cancellation
4.9 (49)
from
$285
St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton

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

4.9 (50)

St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton

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 (50)
from
$309

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