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Top 10 Best Caribbean Sailing Trips

Found 363 Sailing Trips activities in Caribbean. Sort by Popularity.
 

Dolphin Catamaran Snorkel and Sail with Open Bar

(4.7 of 1,901 reviews)

Enjoy a delightful 3-hour adventure featuring two captivating snorkeling stops. First, explore the iconic shipwreck "Antilla", a fascinating relic resting beneath the azure waters, brimming with tales of maritime history and intri... More

Free Cancellation
Start From $69.00
 
Dolphin Catamaran Snorkel and Sail with Open Bar

Dolphin Catamaran Snorkel and Sail with Open Bar

  • Caribbean
  • Superb1,901 reviews4.7

Enjoy a delightful 3-hour adventure featuring two captivating snorkeling stops. First, explore the i....

    Free Cancellation
    Start From $69.00
 
 

ATV, Horse Ride, Zipline, Catamaran at Ocean Outpost Park

(4.5 of 906 reviews)

Relax in our Catamaran while it sails on the ocean experiencing her alternating moods. Be refreshed by the cool waters while zipping across the ocean outpost park .Then take a ride on the wild side on an amazing ATV Quad Safari a... More

Free Cancellation
Start From $239.00
 
ATV, Horse Ride, Zipline, Catamaran at Ocean Outpost Park

ATV, Horse Ride, Zipline, Catamaran at Ocean Outpost Park

  • Caribbean
  • Exellent906 reviews4.5

Relax in our Catamaran while it sails on the ocean experiencing her alternating moods. Be refreshed ....

    Free Cancellation
    Start From $239.00
 
 

Swimming Pigs with pickup: Pig can't fly, but they do Swim!

(4.7 of 1,053 reviews)

Are you ready to have some fun in the sun and make unforgettable memories with da coolest pigs in the Caribbean? Look no further than our half-day adventure tour where you’ll get up close and personal with the most popular resid... More

Free Cancellation
Start From $179.00
 
Swimming Pigs with pickup: Pig can't fly, but they do Swim!

Swimming Pigs with pickup: Pig can't fly, but they do Swim!

  • Caribbean
  • Superb1,053 reviews4.7

Are you ready to have some fun in the sun and make unforgettable memories with da coolest pigs in th....

    Free Cancellation
    Start From $179.00
 
 

Aruba Morning Snorkel Sail and Mimosa Brunch

(4.7 of 1,864 reviews)

Start your day on a high note by embarking on a catamaran cruise across the turquoise waters of Aruba. Indulge in a mimosa brunch experience on board while you cruise to three snorkeling spots, where you’ll swim in the clear Car... More

Free Cancellation
Start From $89.00
 
Aruba Morning Snorkel Sail and Mimosa Brunch

Aruba Morning Snorkel Sail and Mimosa Brunch

  • Caribbean
  • Superb1,864 reviews4.7

Start your day on a high note by embarking on a catamaran cruise across the turquoise waters of Arub....

    Free Cancellation
    Start From $89.00
 
 

Saona Island Day Trip From Punta Cana with Lunch and Open Bar

(4.2 of 2,148 reviews)

Experience a stunning day trip to Saona Island! Your adventure begins with a convenient pick-up from your hotel. Travel by catamaran, enjoying the scenic views and lively atmosphere sipping drinks from the open bar and dancing to ... More

Free Cancellation
Start From $78.00
 
Saona Island Day Trip From Punta Cana with Lunch and Open Bar

Saona Island Day Trip From Punta Cana with Lunch and Open Bar

  • Caribbean
  • Exellent2,148 reviews4.2

Experience a stunning day trip to Saona Island! Your adventure begins with a convenient pick-up from....

    Free Cancellation
    Start From $78.00
 
 

5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

(4.9 of 759 reviews)

Come aboard the sailing catamaran "The Phoenix" and leave everything behind. Sail through the stunning sights of St. Maarten, indulge in drinks and fine food - we offer fruits and cake for breakfast and freshly cooked lunch. Enjoy... More

Free Cancellation
Start From $139.00
 
5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

  • Caribbean
  • Superb759 reviews4.9

Come aboard the sailing catamaran "The Phoenix" and leave everything behind. Sail through the stunni....

    Free Cancellation
    Start From $139.00
 
 

Arusun Catamaran Sail with Snorkeling in Aruba

(4.8 of 2,224 reviews)

Have a warm Aruban welcome on board of a beautiful 65-foot catamaran, the Arusun, and spend the most fun, relaxing 2.5 hours exploring the Caribbean Sea. There is no better way to explore the marine life of Aruba then on this extr... More

Free Cancellation
Start From $60.00
 
Arusun Catamaran Sail with Snorkeling in Aruba

Arusun Catamaran Sail with Snorkeling in Aruba

  • Caribbean
  • Superb2,224 reviews4.8

Have a warm Aruban welcome on board of a beautiful 65-foot catamaran, the Arusun, and spend the most....

    Free Cancellation
    Start From $60.00
 
 

Aruba Sunset Sail with Appetizers and Open Bar

(4.5 of 1,735 reviews)

Experience Aruba's spectacular sunset aboard a luxury catamaran. Enjoy views of Palm Beach from the open water as you sip a cocktail and watch the stars come out. Relax as the friendly crew entertains you with local music, dancing... More

Free Cancellation
Start From $79.00
 
Aruba Sunset Sail with Appetizers and Open Bar Likely to Sell Out

Aruba Sunset Sail with Appetizers and Open Bar

  • Caribbean
  • Exellent1,735 reviews4.5

Experience Aruba's spectacular sunset aboard a luxury catamaran. Enjoy views of Palm Beach from the ....

    Free Cancellation
    Start From $79.00
 
 

San Juan Sunset Harbor Boat Ride

(4.6 of 1,140 reviews)

Hop aboard and join us for a captivating journey on a sunset pontoon boat tour, exploring the timeless allure of San Juan Bay, the historical gem of Puerto Rico. Our Sunset Tour offers a perfect fusion of cultural exploration, a... More

Free Cancellation
Start From $99.00
 
San Juan Sunset Harbor Boat Ride Likely to Sell Out

San Juan Sunset Harbor Boat Ride

  • Caribbean
  • Superb1,140 reviews4.6

Hop aboard and join us for a captivating journey on a sunset pontoon boat tour, exploring the timele....

    Free Cancellation
    Start From $99.00
 
 

Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran

(4.7 of 446 reviews)

Welcome aboard the “DOLPHIN”! Join us for an breathtaking sunset sail we’ll make sure it will be the highlight of your vacation! Our professional staff will give you the ultimate service to ensure you’ll have the time of y... More

Free Cancellation
Start From $59.00
 
Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran Likely to Sell Out

Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran

  • Caribbean
  • Superb446 reviews4.7

Welcome aboard the “DOLPHIN”! Join us for an breathtaking sunset sail we’ll make sure it will ....

    Free Cancellation
    Start From $59.00
 
 

Private Catamaran Cruise with Slide & unlimited drinks

(4.9 of 119 reviews)

Enjoy an exciting excursion on a private catamaran that will take you to explore the crystal-clear waters of a tropical paradise. During the trip, you will have the opportunity to immerse yourself in three stops: 1-Snorkel. where... More

Special Offer
Free Cancellation
Private Tour
Start From $791.20
(Saving 11% ) $885.00
 
-11% Private Catamaran Cruise with Slide & unlimited drinks Likely to Sell Out

Private Catamaran Cruise with Slide & unlimited drinks

  • Caribbean
  • Superb119 reviews4.9

Enjoy an exciting excursion on a private catamaran that will take you to explore the crystal-clear w....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $791.20
    (Saving 11% ) $885.00
 
 

2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)

(4.8 of 897 reviews)

There’s no better way to see the setting Caribbean sun than with a Champagne Sail in Turks and Caicos. Sail past the white sand beaches of Grace Bay in Providenciales, sailing for two hours over crystalline waters aboard a spaci... More

Free Cancellation
Private Tour
Start From $121.53
 
2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only) Likely to Sell Out

2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Ad....

  • Caribbean
  • Superb897 reviews4.8

There’s no better way to see the setting Caribbean sun than with a Champagne Sail in Turks and Cai....

    Free Cancellation
    Private Tour
    Start From $121.53
 
 

4-Hour Catamaran Sail and Snorkel Tour from Grace Bay

(4.8 of 1,322 reviews)

Set sail for a relaxing Caribbean journey on this half-day cruise and snorkeling excursion from Providenciales. Hop aboard a world-class catamaran, operated by a friendly and professional crew, who attend to your comfort while sai... More

Free Cancellation
Private Tour
Start From $145.84
 
4-Hour Catamaran Sail and Snorkel Tour from Grace Bay Likely to Sell Out

4-Hour Catamaran Sail and Snorkel Tour from Grace Bay

  • Caribbean
  • Superb1,322 reviews4.8

Set sail for a relaxing Caribbean journey on this half-day cruise and snorkeling excursion from Prov....

    Free Cancellation
    Private Tour
    Start From $145.84
 
 

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island

(4.8 of 1,924 reviews)

Come swim with the resident green sea turtles and tropical fish on this 3 hour snorkel & sail adventure in St. Thomas aboard The VI Cat. From your departure, set sail on our 54-foot US Coast Guard inspected catamaran to the idylli... More

Free Cancellation
Private Tour
Start From $119.00
 
Turtle Cove Catamaran Snorkel and Sail at Little Buck Island Likely to Sell Out

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island

  • Caribbean
  • Superb1,924 reviews4.8

Come swim with the resident green sea turtles and tropical fish on this 3 hour snorkel & sail advent....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Small-Group Cruising and Snorkeling Catamaran Tour

(4.9 of 2,197 reviews)

This small-group sailing and snorkeling catamaran tour is limited to 16 guests per tour; this limited size sets this tour apart from others. With us, you will receive personalized attention. Go swimming in a natural reserve, snork... More

Free Cancellation
Private Tour
Start From $99.00
 
Small-Group Cruising and Snorkeling Catamaran Tour Likely to Sell Out

Small-Group Cruising and Snorkeling Catamaran Tour

  • Caribbean
  • Superb2,197 reviews4.9

This small-group sailing and snorkeling catamaran tour is limited to 16 guests per tour; this limite....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Restless Native Catamaran Sail and Snorkel Tour

(4.8 of 765 reviews)

Get the most out of your time in Bermuda with a 3.5-hour sail on a pink catamaran. Your captain makes for a fun guide as he regales you with intriguing historical anecdotes about the island. Spend about an hour sailing around Berm... More

Free Cancellation
Private Tour
Start From $95.00
 
Restless Native Catamaran Sail and Snorkel Tour Likely to Sell Out

Restless Native Catamaran Sail and Snorkel Tour

  • Caribbean
  • Superb765 reviews4.8

Get the most out of your time in Bermuda with a 3.5-hour sail on a pink catamaran. Your captain make....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Sunset Sail to Boca Catalina with BBQ Dinner

(4.7 of 160 reviews)

This will have 2 hours of Real Sailing with over 4 sails. We are the longest Sailing trip in Aruba at 4.5 hours instead of 2.5 hours. Lunch or dinner is included.... More

Free Cancellation
Private Tour
Start From $119.00
 
Sunset Sail to Boca Catalina with BBQ Dinner Likely to Sell Out

Sunset Sail to Boca Catalina with BBQ Dinner

  • Caribbean
  • Superb160 reviews4.7

This will have 2 hours of Real Sailing with over 4 sails. We are the longest Sailing trip in Aruba a....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

San Juan: Snorkeling with Turtles Adventure and Free Videos

(4.9 of 123 reviews)

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in small groups of up to 10, ensuring a personalized and high-quality experience... More

Free Cancellation
Private Tour
Start From $57.00
 
San Juan: Snorkeling with Turtles Adventure and Free Videos Likely to Sell Out

San Juan: Snorkeling with Turtles Adventure and Free Videos

  • Caribbean
  • Superb123 reviews4.9

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginn....

    Free Cancellation
    Private Tour
    Start From $57.00
 
 

Prickly Pear Catamaran Trip from St Maarten Including Lunch

(4.5 of 280 reviews)

Discover the paradise shores of Prickly Pear Islands on this full-day trip from St Maarten. Sail aboard Lambada catamaran and stop at Prickly Pear Island, one of Anguilla’s offshore cays, where you’ll snorkel in clear turquois... More

Free Cancellation
Private Tour
Start From $135.00
 
Prickly Pear Catamaran Trip from St Maarten Including Lunch Likely to Sell Out

Prickly Pear Catamaran Trip from St Maarten Including Lunch

  • Caribbean
  • Exellent280 reviews4.5

Discover the paradise shores of Prickly Pear Islands on this full-day trip from St Maarten. Sail abo....

    Free Cancellation
    Private Tour
    Start From $135.00
 
 

Private Luxury Catamaran Yacht. Full or Half Day Charter - Sail, Beach, Snorkel.

(4.9 of 353 reviews)

Spend the day on your own Luxury Yacht. This price is all inclusive for the Yacht, up to 12 people. You can select a half or full day charter. Visit the islands and harbors of St. Thomas, Buck Island, Water Island, and maybe even ... More

Free Cancellation
Private Tour
Start From $1,495.00
 
Private Luxury Catamaran Yacht. Full or Half Day Charter - Sail, Beach, Snorkel. Likely to Sell Out

Private Luxury Catamaran Yacht. Full or Half Day Charter - Sail, ....

  • Caribbean
  • Superb353 reviews4.9

Spend the day on your own Luxury Yacht. This price is all inclusive for the Yacht, up to 12 people. ....

    Free Cancellation
    Private Tour
    Start From $1,495.00
 
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