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Top 10 Best St Thomas Sailing Trips

Found 50 Sailing Trips activities in St Thomas. Sort by Popularity. - Page 2
 

Half Day Private Sail and Snorkel Trip to St John

(5 of 47 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

  • St Thomas
  • Superb47 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
 
 

Power Catamaran Snorkel & Beach Break

(4.9 of 59 reviews)

Join us for an unforgettable 3.75-hour adventure aboard the mighty 1000hp "Breeze" PowerCat! Island-Hop, Snorkel, and Unwind Explore two of the Caribbean's hottest spots: 1. Buck Island: Dive into crystal-clear waters teeming wit... More

Free Cancellation
Private Tour
Start From $79.00
 
Power Catamaran Snorkel & Beach Break

Power Catamaran Snorkel & Beach Break

  • St Thomas
  • Superb59 reviews4.9

Join us for an unforgettable 3.75-hour adventure aboard the mighty 1000hp "Breeze" PowerCat! Island....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

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

(4.8 of 72 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

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

  • St Thomas
  • Superb72 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
 
 

Sunset Sail from the Westin Frenchman's Reef

(4.8 of 72 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

  • St Thomas
  • Superb72 reviews4.8

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
 
 

Sunset Harbor Cruise of Charlotte Amalie

(5 of 9 reviews)

Relax and wind down after a day of fun-filled activities in St. Thomas! Board the Castaway Girl and sail through the picturesque harbor of Charlotte Amalie. While the wind is blowing through your hair, enjoy complimentary champagn... More

Free Cancellation
Private Tour
Start From $89.00
 
Sunset Harbor Cruise of Charlotte Amalie Likely to Sell Out

Sunset Harbor Cruise of Charlotte Amalie

  • St Thomas
  • Superb9 reviews5

Relax and wind down after a day of fun-filled activities in St. Thomas! Board the Castaway Girl and ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Private Sunset Sailor's Delight from Sapphire Marina

(5 of 11 reviews)

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 aboard our beautiful 40ft classic sailboat. The sailor's delight trip is a favorite by many and sure to ... More

Free Cancellation
Private Tour
Start From $695.00
 
Private Sunset Sailor's Delight from Sapphire Marina Likely to Sell Out

Private Sunset Sailor's Delight from Sapphire Marina

  • St Thomas
  • Superb11 reviews5

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

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

All Inclusive St. John Boating Adventure

(5 of 76 reviews)

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 and authentic day at sea. We offer snorkeling options for all skill levels and swi... More

Free Cancellation
Private Tour
Start From $635.00
 
All Inclusive St. John Boating Adventure Likely to Sell Out

All Inclusive St. John Boating Adventure

  • St Thomas
  • Superb76 reviews5

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National P....

    Free Cancellation
    Private Tour
    Start From $635.00
 
 

Full Day Private Charter on Luxury Catamaran Sailing.

(4.9 of 75 reviews)

Swim with sea turtles and snorkel beautiful reefs. See the amazing beaches and Islands while catching some sun on the bean bags on top of the trampolines. You will enjoy the smooth ride of our beautiful sailing catamaran. You wi... More

Free Cancellation
Private Tour
Start From $250.00
 
Full Day Private Charter on Luxury Catamaran Sailing. Likely to Sell Out

Full Day Private Charter on Luxury Catamaran Sailing.

  • St Thomas
  • Superb75 reviews4.9

Swim with sea turtles and snorkel beautiful reefs. See the amazing beaches and Islands while catchin....

    Free Cancellation
    Private Tour
    Start From $250.00
 
 

Private Full Day Sail in Virgin Islands National Park

(5 of 14 reviews)

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 of the most beautiful areas in the Virgin Islands and provide you with their expert knowledge. Lunch will... More

Free Cancellation
Private Tour
Start From $1,550.00
 
Private Full Day Sail in Virgin Islands National Park Likely to Sell Out

Private Full Day Sail in Virgin Islands National Park

  • St Thomas
  • Superb14 reviews5

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

    Free Cancellation
    Private Tour
    Start From $1,550.00
 
 

Full Day Private Charter (55' Sailing Yacht and up to 12 guests)

(5 of 82 reviews)

Explore the Virgin Islands in style and luxury aboard this beautiful 54 foot sailing yacht for an amazing full day (10am - 4pm) sailing excursion. Relax and enjoy snorkeling the crystal clear waters of the Virgin Islands while you... More

Special Offer
Free Cancellation
Private Tour
Start From $1,715.00
(Saving 30% ) $2,450.00
 
-30% Full Day Private Charter (55' Sailing Yacht and up to 12 guests) Likely to Sell Out

Full Day Private Charter (55' Sailing Yacht and up to 12 guests)

  • St Thomas
  • Superb82 reviews5

Explore the Virgin Islands in style and luxury aboard this beautiful 54 foot sailing yacht for an am....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,715.00
    (Saving 30% ) $2,450.00
 
 

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

(3 of 2 reviews)

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 in crystal blue waters, enjoy lite bites and a full bar. Explore St. John o... More

Free Cancellation
Private Tour
Start From $129.00
 
Sail, Shop and Snorkel in St. John from Frenchman's Reef Likely to Sell Out

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

  • St Thomas

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 $129.00
 
 

Private Day Charter Classic Sailboat

(5 of 65 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

  • St Thomas
  • Superb65 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
 
 

Private Day Sail & Snorkel with Virgin Islands Day Sailing, 6 guest max

(5 of 96 reviews)

A Private 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 memori... More

Free Cancellation
Private Tour
Start From $1,260.00
 
Private Day Sail & Snorkel with Virgin Islands Day Sailing, 6 guest max Likely to Sell Out

Private Day Sail & Snorkel with Virgin Islands Day Sailing, 6 gue....

  • St Thomas
  • Superb96 reviews5

A Private Sailing Experience, Just for You. There is no end to what you can see while sailing with V....

    Free Cancellation
    Private Tour
    Start From $1,260.00
 
 

Pizza Pi, Snorkel & Sunset Sail

(5 of 23 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

  • St Thomas
  • Superb23 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
 
 

Legacy Waterfront Harbor Dinner Sail from Frenchman's Reef

(5 of 1 review)

Enjoy dinner service complimented by an open bar on the Flying Frenchman, the newest and most luxurious catamaran in our fleet. Take in a magnificent Caribbean sunset while under sail and enjoying special locally inspired cuisine,... More

Free Cancellation
Private Tour
Start From $209.00
 
Legacy Waterfront Harbor Dinner Sail from Frenchman's Reef Likely to Sell Out

Legacy Waterfront Harbor Dinner Sail from Frenchman's Reef

  • St Thomas
  • Superb1 review5

Enjoy dinner service complimented by an open bar on the Flying Frenchman, the newest and most luxuri....

    Free Cancellation
    Private Tour
    Start From $209.00
 
 

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

(5 of 3 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!

  • St Thomas
  • Superb3 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
 
 

PiZZA Pi Snorkel Sail from Frenchman's Reef

(5 of 1 review)

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

  • St Thomas
  • Superb1 review5

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
 
 

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

  • St Thomas
  • 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
 
 

Private USVI Sailing Catamaran Charter

(5 of 4 reviews)

Embark on an adventure aboard SY Argo, a 41-foot Maine Cat offering a private luxury sailing experience in the mesmerizing US Virgin Islands. With a generous capacity of up to 31 guests, the catamaran promises exploration and rela... More

Free Cancellation
Private Tour
Start From $3,315.00
 
Private USVI Sailing Catamaran Charter Likely to Sell Out

Private USVI Sailing Catamaran Charter

  • St Thomas
  • Superb4 reviews5

Embark on an adventure aboard SY Argo, a 41-foot Maine Cat offering a private luxury sailing experie....

    Free Cancellation
    Private Tour
    Start From $3,315.00
 
 

Private Sunset Sail

(5 of 3 reviews)

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 sail you through the tranquil waters of the USVI and beyond. Our experienced captain and crew will sai... More

Free Cancellation
Private Tour
Start From $1,395.00
 
Private Sunset Sail Likely to Sell Out

Private Sunset Sail

  • St Thomas
  • Superb3 reviews5

You will set sail aboard one of the largest daysail yachts in the Virgin Islands. At 55 feet the Blu....

    Free Cancellation
    Private Tour
    Start From $1,395.00
 
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