Top US Virgin Islands Sailing Trips

Q: I need a ride! Which US Virgin Islands Sailing Trips have Hotel Pickup?

No problem. These US Virgin Islands Sailing Trips include Hotel Pickup: Private Day Charter Classic Sailboat All Inclusive St. John Boating Adventure Discover the Best of St. John - Snorkel, Beach & Shopping! View all Tours with Hotel Pickup →

Q: Got any more US Virgin Islands trip ideas?

We sure do. Check out our curated lists of hand-picked US Virgin Islands Tours. Top 10 US Virgin Islands 2026 Senior-friendly tours US Virgin Islands The best tours and activities for culture lovers in US Virgin Islands Top Day Trips from US Virgin Islands Things to do in US Virgin Islands this summer View all US Virgin Islands Trip Ideas →

Q: What are the most popular styles of Tours and Activities in US Virgin Islands?

Based on our sales data over the past year, the most popular styles of tours and activities in US Virgin Islands are: US Virgin Islands Water Sports US Virgin Islands Kayaking & Canoeing US Virgin Islands Snorkeling US Virgin Islands Luxury & Special Occasions US Virgin Islands Luxury Tours View all tour styles in US Virgin Islands →

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

5.0 (79)

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...

5 hours Hotel pickup offered Free Cancellation

5.0 (79)

from
$314

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

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

4.9 (207)

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...

8 hours Free Cancellation

4.9 (207)

from
$289

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

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

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

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

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

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

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

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

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

5.0 (32)

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...

2 hours 30 minutes Free Cancellation

5.0 (32)

from
$245

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

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

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

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

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 (1,058)

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 (1,058)

from
$150

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

4.9 (350)

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...

6 hours 30 minutes Free Cancellation

4.9 (350)

from
$149

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

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

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

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. 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

4.9 (174)

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...

5 hours Free Cancellation

4.9 (174)

from
$129

Frequently Asked Questions

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

What are the best options for US Virgin Islands Sailing Trips?

What are the best kid-friendly options for US Virgin Islands Sailing Trips Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly US Virgin Islands Sailing Trips are:

View all kid-friendly Tours →

Which US Virgin Islands Sailing Trips have Instant Confirmation?

US Virgin Islands Sailing Trips with Instant Confirmation include:

View all Tours with Instant Confirmation →

Which US Virgin Islands Sailing Trips have Free Cancellation?

US Virgin Islands Sailing Trips with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which US Virgin Islands Sailing Trips have Hotel Pickup?

Got any more US Virgin Islands trip ideas?

What are the most popular styles of Tours and Activities in US Virgin Islands?