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Top US Virgin Islands Sailing Trips

48 Results
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
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

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
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

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
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

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
Luxury Private Sunset Cruise for up to 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

Likely to Sell Out
Likely to Sell Out

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 (38)
from
$695
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
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

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
Private Sailing Tour of Pirate Waters and Shipwrecks

Salt River Bay, St. Croix, was a pirate nest for two and a half centuries, used by Kalinago, Conquistadors, Buccaneers, and Pirates, and appears almost …More

Salt River Bay, St. Croix, was a pirate nest for two and a half centuries, used by Kalinago, Conquistadors, Buccaneers, and Pirates, and appears almost...

2 hours Free Cancellation
4.9 (24)
from
$75
Simply Sailing Private Sail from Sapphire Marina

This is the ideal trip for the true sailor's out there. Enjoy a private 3 hour adventure of straight sailing aboard our beautiful "Robert Perry" …More

Likely to Sell Out
Likely to Sell Out

This is the ideal trip for the true sailor's out there. Enjoy a private 3 hour adventure of straight sailing aboard our beautiful "Robert Perry"...

3 hours Free Cancellation
5.0 (19)
from
$799
Private Full Day Sail/ Snorkel Experience USVI (Sapphire Marina, STT pick up)

This is a private personal sailing experience for up to six guest. Avoid the crowds and choose how you want to spend the best day …More

Likely to Sell Out
Likely to Sell Out

This is a private personal sailing experience for up to six guest. Avoid the crowds and choose how you want to spend the best day...

7 hours Free Cancellation
5.0 (18)
from
$1,975
Private Full Day Sail in Virgin Islands National Park

On a private full day sail with Max Charters you will have the boat to yourself! Your captain and mate will take you to some …More

Likely to Sell Out
Likely to Sell Out

On a private full day sail with Max Charters you will have the boat to yourself! Your captain and mate will take you to some...

6 hours Free Cancellation
5.0 (16)
from
$1,650
Private Sunset Sailor's Delight from Sapphire Marina

This is an private intimate trip for up to six guest. Avoid the crowds and enjoy a 2 hour leisurely sail with your loved ones …More

Likely to Sell Out
Likely to Sell Out

This is an private intimate trip for up to six guest. Avoid the crowds and enjoy a 2 hour leisurely sail with your loved ones...

2 hours Free Cancellation
5.0 (15)
from
$795
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
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

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
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
Private Sunset Sail, Open Bar, 12 Guests, Amazing Island Views

You will set sail aboard one of the largest daysail yachts in the Virgin Islands. At 55 feet the Blue Dream is well equipped to …More

Likely to Sell Out
Likely to Sell Out

You will set sail aboard one of the largest daysail yachts in the Virgin Islands. At 55 feet the Blue Dream is well equipped to...

2 hours Free Cancellation
5.0 (6)
from
$1,345
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
I Like Turtles Private Sailing and Snorkeling from Sapphire

Come sail on a beautiful classic monohaul sailboat. You're guaranteed to enjoy your day sailing and snorkeling with amazing green sea turtles here in the …More

Likely to Sell Out
Likely to Sell Out

Come sail on a beautiful classic monohaul sailboat. You're guaranteed to enjoy your day sailing and snorkeling with amazing green sea turtles here in the...

3 hours Free Cancellation
5.0 (3)
from
$799
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

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