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Top 10 Best US Virgin Islands Sailing Trips

Found 65 Sailing Trips activities in US Virgin Islands. Sort by Popularity. - Page 2
 

Half Day Private Sail and Snorkel Trip to St John

(5 of 54 reviews)

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 beachcombing, followed by snacks, drinks, then more sailing. Captain Ryan... More

Free Cancellation
Private Tour
Start From $165.00
 
Half Day Private Sail and Snorkel Trip to St John

Half Day Private Sail and Snorkel Trip to St John

  • US Virgin Islands
  • Superb54 reviews5

Sail with Liberty guests experience real sailing on our spacious, private catamaran. We sail you to ....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

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

(4.8 of 30 reviews)

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 charters. After checking in at the Ritz-Carlton on St. Thomas, guests board our 55′ catamaran for a tr... More

Free Cancellation
Private Tour
Start From $319.00
 
St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton Likely to Sell Out

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

  • US Virgin Islands
  • Superb30 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $319.00
 
 

Days End Sunset Sail from the Westin at Frenchman's Reef

(4.4 of 17 reviews)

Step aboard the Flying Frenchman, our newly designed, state-of-the-art, luxury sailing catamaran for a fun and relaxing sunset sail departing from Frenchman’s Reef. Take in a magnificent Caribbean sunset while under sail and enj... More

Free Cancellation
Private Tour
Start From $99.00
 
Days End Sunset Sail from the Westin at Frenchman's Reef Likely to Sell Out

Days End Sunset Sail from the Westin at Frenchman's Reef

  • US Virgin Islands
  • Exellent17 reviews4.4

Step aboard the Flying Frenchman, our newly designed, state-of-the-art, luxury sailing catamaran for....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Swim w/Turtles in St. John, Pizza Pi & Snorkel a shipwreck.

(4.9 of 393 reviews)

** This trip departs from St. Thomas Only ** This very personalized tour takes only a maximum of 12 guests and is the BEST way to experience swimming with Turtles in the Virgin Islands. After you board, you'll get to enjoy Mimos... More

Free Cancellation
Private Tour
Start From $275.00
 
Swim w/Turtles in St. John, Pizza Pi & Snorkel a shipwreck. Likely to Sell Out

Swim w/Turtles in St. John, Pizza Pi & Snorkel a shipwreck.

  • US Virgin Islands
  • Superb393 reviews4.9

** This trip departs from St. Thomas Only ** This very personalized tour takes only a maximum of 12....

    Free Cancellation
    Private Tour
    Start From $275.00
 
 

St. Thomas Sunset Sail, Serenity at Sea

(5 of 20 reviews)

Experience serenity at sea on our St Thomas Sunset Sail! Enjoy champagne, rum drinks, and hors d'oeuvres while taking in breathtaking views of the harbor and sunset. Book now and create unforgettable memories on this 60ft catamara... More

Free Cancellation
Private Tour
Start From $89.00
 
St. Thomas Sunset Sail, Serenity at Sea Likely to Sell Out

St. Thomas Sunset Sail, Serenity at Sea

  • US Virgin Islands
  • Superb20 reviews5

Experience serenity at sea on our St Thomas Sunset Sail! Enjoy champagne, rum drinks, and hors d'oeu....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

PiZZA Pi Snorkel Sail from Frenchman's Reef

(5 of 2 reviews)

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 pizza from the Virgin Island’s ONLY floating food boat, PiZZA Pi, VI. We also include an open... More

Free Cancellation
Private Tour
Start From $139.00
 
PiZZA Pi Snorkel Sail from Frenchman's Reef Likely to Sell Out

PiZZA Pi Snorkel Sail from Frenchman's Reef

  • US Virgin Islands
  • Superb2 reviews5

Start the day with a sail to an offshore cay for premier snorkeling. In addition to fruit, salads, a....

    Free Cancellation
    Private Tour
    Start From $139.00
 
 

Private Day Charter Classic Sailboat

(5 of 68 reviews)

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 ports of St Thomas to meet near the commuter ferry terminal in Cruz Bay. The ferry ta... More

Free Cancellation
Private Tour
Start From $1,395.00
 
Private Day Charter Classic Sailboat Likely to Sell Out

Private Day Charter Classic Sailboat

  • US Virgin Islands
  • Superb68 reviews5

To maximize your day and our destination options in the National Park, we offer flexible timing allo....

    Free Cancellation
    Private Tour
    Start From $1,395.00
 
 

St. John Sail with Bar and Hors d'Oeuvres to Lovango Dinner

(4.5 of 28 reviews)

The private island escape of Lovango Resort + Beach Club is the newest go-to destination in the USVI. Enjoy an unforgettable waterfront meal with breathtaking views looking out over Pillsbury Bay with St. John in the distance, whi... More

Free Cancellation
Private Tour
Start From $119.00
 
St. John Sail with Bar and Hors d'Oeuvres to Lovango Dinner Likely to Sell Out

St. John Sail with Bar and Hors d'Oeuvres to Lovango Dinner

  • US Virgin Islands
  • Exellent28 reviews4.5

The private island escape of Lovango Resort + Beach Club is the newest go-to destination in the USVI....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Sail Into the Sunset with Virgin Islands Day Sail - 6 Guest max

(4.8 of 74 reviews)

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 as we explore the most breathtaking locations around the Virgin Islands. Create timeless... More

Free Cancellation
Private Tour
Start From $110.00
 
Sail Into the Sunset with Virgin Islands Day Sail - 6 Guest max Likely to Sell Out

Sail Into the Sunset with Virgin Islands Day Sail - 6 Guest max

  • US Virgin Islands
  • Superb74 reviews4.8

An Unforgettable Sailing Experience, Just for You. There is no end to what you can see while sailing....

    Free Cancellation
    Private Tour
    Start From $110.00
 
 

St. Thomas & St. John Private Luxury Full-Day Sail

(5 of 50 reviews)

If you’re looking for an unforgettable day at sea, book a private boat charter with Sweet Pea Charters. Our luxury 40 by 25 foot catamaran is the perfect vessel to take you on a personalized tour of the stunning U.S. Virgin Isla... More

Free Cancellation
Private Tour
Start From $1,450.00
 
St. Thomas & St. John Private Luxury Full-Day Sail Likely to Sell Out

St. Thomas & St. John Private Luxury Full-Day Sail

  • US Virgin Islands
  • Superb50 reviews5

If you’re looking for an unforgettable day at sea, book a private boat charter with Sweet Pea Char....

    Free Cancellation
    Private Tour
    Start From $1,450.00
 
 

Private Sunset Cruise out of Sapphire Beach Marina, 6 Guest max

(5 of 28 reviews)

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 as we explore the most breathtaking locations around the Virgin Islands. Create timeless... More

Free Cancellation
Private Tour
Start From $630.00
 
Private Sunset Cruise out of Sapphire Beach Marina, 6 Guest max Likely to Sell Out

Private Sunset Cruise out of Sapphire Beach Marina, 6 Guest max

  • US Virgin Islands
  • Superb28 reviews5

An Unforgettable Sailing Experience, Just for You. There is no end to what you can see while sailing....

    Free Cancellation
    Private Tour
    Start From $630.00
 
 

Group Sunset Sail St. John

(5 of 31 reviews)

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 on the water? Join us for our all inclusive private day sail adventure as well! ... More

Free Cancellation
Private Tour
Start From $400.00
 
Group Sunset Sail St. John Likely to Sell Out

Group Sunset Sail St. John

  • US Virgin Islands
  • Superb31 reviews5

We are a family owned small business; we have a love for true sailing and authentic relationships he....

    Free Cancellation
    Private Tour
    Start From $400.00
 
 

Private Sailing Tour of Pirate Waters and Shipwrecks

(4.9 of 22 reviews)

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 as pristine as when they anchored in the bay, sold their plunder, and partied ... More

Free Cancellation
Private Tour
Start From $175.00
 
Private Sailing Tour of Pirate Waters and Shipwrecks Likely to Sell Out

Private Sailing Tour of Pirate Waters and Shipwrecks

  • US Virgin Islands
  • Superb22 reviews4.9

Salt River Bay, St. Croix, was a pirate nest for two and a half centuries, used by Kalinago, Conquis....

    Free Cancellation
    Private Tour
    Start From $175.00
 
 

Sunset Sail from the Westin Frenchman's Reef

(4.9 of 22 reviews)

Step aboard the Flying Frenchman, our newly designed, state-of-the art sailing catamaran for a fun and festive sunset sail departing from Frenchman’s Reef. Take in a magnificent Caribbean sunset while under sail and enjoying the... More

Free Cancellation
Private Tour
Start From $89.00
 
Sunset Sail from the Westin Frenchman's Reef Likely to Sell Out

Sunset Sail from the Westin Frenchman's Reef

  • US Virgin Islands
  • Superb22 reviews4.9

Step aboard the Flying Frenchman, our newly designed, state-of-the art sailing catamaran for a fun a....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Maho Bay Turtle Snorkel with Lunch and Bar at Frenchman's Reef

(5 of 1 review)

Embark on a snorkeling adventure to Maho Bay, a pristine paradise known for crystal-clear waters and vibrant marine life. Feel the salty breeze as you make your way to the bay on power catamaran, Jost Boat. The journey is a feast ... More

Free Cancellation
Private Tour
Start From $139.00
 
Maho Bay Turtle Snorkel with Lunch and Bar at Frenchman's Reef Likely to Sell Out

Maho Bay Turtle Snorkel with Lunch and Bar at Frenchman's Reef

  • US Virgin Islands
  • Superb1 review5

Embark on a snorkeling adventure to Maho Bay, a pristine paradise known for crystal-clear waters and....

    Free Cancellation
    Private Tour
    Start From $139.00
 
 

Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

(5 of 103 reviews)

The Virgin Islands are the sailing capital of the world!! Sail with us from St. Thomas to the exotic island of Jost Van Dyke. This trip is limited to only 12 guests. A light continental Breakfast and a full open bar w/bottomless... More

Free Cancellation
Private Tour
Start From $375.00
 
Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar) Likely to Sell Out

Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

  • US Virgin Islands
  • Superb103 reviews5

The Virgin Islands are the sailing capital of the world!! Sail with us from St. Thomas to the exotic....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

Pizza Pi, Snorkel & Sunset Sail

(5 of 34 reviews)

**New Stormy Pirates Itinerary* As with every Stormy Pirates tour, this is a small group tour with only a maximum of 12 guests. We depart from American Yacht Harbor in Red Hook and sail to world famous Pizza Pi, where you will ... More

Free Cancellation
Private Tour
Start From $175.00
 
Pizza Pi, Snorkel & Sunset Sail Likely to Sell Out

Pizza Pi, Snorkel & Sunset Sail

  • US Virgin Islands
  • Superb34 reviews5

**New Stormy Pirates Itinerary* As with every Stormy Pirates tour, this is a small group tour with ....

    Free Cancellation
    Private Tour
    Start From $175.00
 
 

Private Island Boat tour, Snorkel & Discover hidden Treasures !

(5 of 5 reviews)

We can have a tour on our lovely motor sail boat Treasure where its not crowded and can take maximum of 6 we can go to the inhabitable Secret Saba Island if weather conditions are good to where we can snorkel there in a transpare... More

Free Cancellation
Private Tour
Start From $79.00
 
Private Island Boat tour, Snorkel & Discover hidden Treasures ! Likely to Sell Out

Private Island Boat tour, Snorkel & Discover hidden Treasures !

  • US Virgin Islands
  • Superb5 reviews5

We can have a tour on our lovely motor sail boat Treasure where its not crowded and can take maximum....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Discover the Best of St. John - Snorkel, Beach & Shopping!

(5 of 4 reviews)

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 in crystal blue waters, enjoy lite bites (hors d'ouevres) and a full bar. Explor... More

Free Cancellation
Private Tour
Start From $159.00
 
Discover the Best of St. John - Snorkel, Beach & Shopping! Likely to Sell Out

Discover the Best of St. John - Snorkel, Beach & Shopping!

  • US Virgin Islands
  • Superb4 reviews5

Experience the best of two tropical islands! Sail to the island escape of St. John from St. Thomas a....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Cruz Bay Champagne Sunset Sail with Open Bar & Hors D'oeuvres

(4.3 of 58 reviews)

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 sail aboard our 55′ catamaran, Daydreamer. Enjoy a relaxing and romantic sail in ... More

Free Cancellation
Private Tour
Start From $99.00
 
Cruz Bay Champagne Sunset Sail with Open Bar & Hors D'oeuvres Likely to Sell Out

Cruz Bay Champagne Sunset Sail with Open Bar & Hors D'oeuvres

  • US Virgin Islands
  • Exellent58 reviews4.3

As the sun sets our sails rise, and the champagne flows. Experience a Caribbean sunset and celebrate....

    Free Cancellation
    Private Tour
    Start From $99.00
 
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