Sailing Trips in Caribbean
Top 10 Best Caribbean Sailing Trips
Found 330 Sailing Trips activities in Caribbean. Sort by Popularity.ATV, Horse Ride, Zipline, Catamaran at Ocean Outpost Park
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
![ATV, Horse Ride, Zipline, Catamaran at Ocean Outpost Park ATV, Horse Ride, Zipline, Catamaran at Ocean Outpost Park](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/11/d7/ac/5d.jpg)
ATV, Horse Ride, Zipline, Catamaran at Ocean Outpost Park
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Caribbean
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Exellent816 reviews4.5
Relax in our Catamaran while it sails on the ocean experiencing her alternating moods. Be refreshed ....
Aruba Sunset Sail with Appetizers and Open Bar
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
![Aruba Sunset Sail with Appetizers and Open Bar Aruba Sunset Sail with Appetizers and Open Bar](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/12/e7/89/20.jpg)
Aruba Sunset Sail with Appetizers and Open Bar
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Caribbean
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Exellent1,472 reviews4.5
Experience Aruba's spectacular sunset aboard a luxury catamaran. Enjoy views of Palm Beach from the ....
Dolphin Catamaran Snorkel and Sail with Open Bar
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
![Dolphin Catamaran Snorkel and Sail with Open Bar Dolphin Catamaran Snorkel and Sail with Open Bar](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0a/48/61/b1.jpg)
Dolphin Catamaran Snorkel and Sail with Open Bar
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Caribbean
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Superb1,632 reviews4.7
Enjoy a delightful 3-hour adventure featuring two captivating snorkeling stops. First, explore the i....
5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix
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
![5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix 5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/11/c0/a1/0d.jpg)
5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix
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Caribbean
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Superb602 reviews4.9
Come aboard the sailing catamaran "The Phoenix" and leave everything behind. Sail through the stunni....
Swimming Pigs with pickup: Pig can't fly, but they do Swim!
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
![Swimming Pigs with pickup: Pig can't fly, but they do Swim! Swimming Pigs with pickup: Pig can't fly, but they do Swim!](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/13/16/4d/79.jpg)
Swimming Pigs with pickup: Pig can't fly, but they do Swim!
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Caribbean
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Superb931 reviews4.7
Are you ready to have some fun in the sun and make unforgettable memories with da coolest pigs in th....
Aruba Morning Snorkel Sail and Mimosa Brunch
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
![Aruba Morning Snorkel Sail and Mimosa Brunch Aruba Morning Snorkel Sail and Mimosa Brunch](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/7d/a8/50.jpg)
Aruba Morning Snorkel Sail and Mimosa Brunch
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Caribbean
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Superb1,673 reviews4.7
Start your day on a high note by embarking on a catamaran cruise across the turquoise waters of Arub....
Saona Island Day Trip From Punta Cana with Lunch and Open Bar
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
![Saona Island Day Trip From Punta Cana with Lunch and Open Bar Saona Island Day Trip From Punta Cana with Lunch and Open Bar](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/71/e5/77.jpg)
Saona Island Day Trip From Punta Cana with Lunch and Open Bar
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Caribbean
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Exellent1,796 reviews4.2
Experience a stunning day trip to Saona Island! Your adventure begins with a convenient pick-up from....
San Juan Sunset Harbor Boat Ride
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
![San Juan Sunset Harbor Boat Ride San Juan Sunset Harbor Boat Ride](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/13/16/f3/9d.jpg)
San Juan Sunset Harbor Boat Ride
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Caribbean
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Superb998 reviews4.6
Hop aboard and join us for a captivating journey on a sunset pontoon boat tour, exploring the timele....
Arusun Catamaran Sail with Snorkeling in Aruba
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
![Arusun Catamaran Sail with Snorkeling in Aruba Arusun Catamaran Sail with Snorkeling in Aruba](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/08/78/d8/29.jpg)
Arusun Catamaran Sail with Snorkeling in Aruba
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Caribbean
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Superb2,036 reviews4.8
Have a warm Aruban welcome on board of a beautiful 65-foot catamaran, the Arusun, and spend the most....
4-Hour Catamaran Sail and Snorkel Tour from Grace Bay
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
![4-Hour Catamaran Sail and Snorkel Tour from Grace Bay 4-Hour Catamaran Sail and Snorkel Tour from Grace Bay](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/81/73/0c.jpg)
4-Hour Catamaran Sail and Snorkel Tour from Grace Bay
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Caribbean
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Superb1,210 reviews4.8
Set sail for a relaxing Caribbean journey on this half-day cruise and snorkeling excursion from Prov....
Turtle Cove Catamaran Snorkel and Sail at Little Buck Island
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
![Turtle Cove Catamaran Snorkel and Sail at Little Buck Island Turtle Cove Catamaran Snorkel and Sail at Little Buck Island](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0b/38/f1/95.jpg)
Turtle Cove Catamaran Snorkel and Sail at Little Buck Island
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Caribbean
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Superb1,754 reviews4.8
Come swim with the resident green sea turtles and tropical fish on this 3 hour snorkel & sail advent....
Aruba Sunset Sail Cruise aboard The Dolphin Catamaran
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
![Aruba Sunset Sail Cruise aboard The Dolphin Catamaran Aruba Sunset Sail Cruise aboard The Dolphin Catamaran](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0b/2f/4d/b6.jpg)
Aruba Sunset Sail Cruise aboard The Dolphin Catamaran
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Caribbean
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Superb345 reviews4.6
Welcome aboard the “DOLPHIN”! Join us for an breathtaking sunset sail we’ll make sure it will ....
Historical San Juan Bay Sunset Sailing Tour
Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind, the peace from no engine noise, no crowds, no fake pirates, no crowds, no need to scream. We sail aboard a real racer cruiser (J3... More
![Historical San Juan Bay Sunset Sailing Tour Historical San Juan Bay Sunset Sailing Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/06/7e/48/e5.jpg)
Historical San Juan Bay Sunset Sailing Tour
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Caribbean
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Exellent572 reviews4.5
Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind,....
Aruba Sunset Cruise: Dine by the Seaside
Spend a relaxing evening in Aruba on a sunset cruise followed by a waterfront seafood dinner. Sail along Aruba’s west coast, enjoying snacks and an open bar while you wait for the famous Caribbean sunset. After two hours on the ... More
![Aruba Sunset Cruise: Dine by the Seaside Aruba Sunset Cruise: Dine by the Seaside](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/a6/09/7e.jpg)
Aruba Sunset Cruise: Dine by the Seaside
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Caribbean
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Exellent808 reviews4.4
Spend a relaxing evening in Aruba on a sunset cruise followed by a waterfront seafood dinner. Sail a....
![Sunset Sail to Boca Catalina with BBQ Dinner Sunset Sail to Boca Catalina with BBQ Dinner](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/12/28/87/35.jpg)
Sunset Sail to Boca Catalina with BBQ Dinner
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Caribbean
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Superb50 reviews4.8
This will have 2 hours of Real Sailing with over 4 sails. We are the longest Sailing trip in Aruba a....
2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)
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
![2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only) 2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0b/a0/bf/73.jpg)
2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Ad....
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Caribbean
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Superb810 reviews4.8
There’s no better way to see the setting Caribbean sun than with a Champagne Sail in Turks and Cai....
Small-Group Cruising and Snorkeling Catamaran Tour
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
![Small-Group Cruising and Snorkeling Catamaran Tour Small-Group Cruising and Snorkeling Catamaran Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/72/04/7f.jpg)
Small-Group Cruising and Snorkeling Catamaran Tour
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Caribbean
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Superb1,995 reviews4.9
This small-group sailing and snorkeling catamaran tour is limited to 16 guests per tour; this limite....
Restless Native Catamaran Sail and Snorkel Tour
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
![Restless Native Catamaran Sail and Snorkel Tour Restless Native Catamaran Sail and Snorkel Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/11/a7/c4/2a.jpg)
Restless Native Catamaran Sail and Snorkel Tour
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Caribbean
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Superb733 reviews4.8
Get the most out of your time in Bermuda with a 3.5-hour sail on a pink catamaran. Your captain make....
Barbados -Luxury Cruise with Lunch and Open Bar
We are the newest pinnacle of luxury, our 30ft double-decker pontoon boat in Barbados distinguishes itself with an exceptional crew, delightful cuisine, and unparalleled service. This experience seamlessly merges state-of-the-art ... More
![Barbados -Luxury Cruise with Lunch and Open Bar Barbados -Luxury Cruise with Lunch and Open Bar](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/12/6d/b6/07.jpg)
Barbados -Luxury Cruise with Lunch and Open Bar
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Caribbean
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Superb22 reviews4.6
We are the newest pinnacle of luxury, our 30ft double-decker pontoon boat in Barbados distinguishes ....
Aruba Sunset Sail Experience
Unwind and end your day on a high note with this relaxing cruise. Climb aboard a comfortable open-deck catamaran and set sail to admire Aruba's crystal waters, breathtaking shoreline, and beautiful sunset. Along the way, sip a tro... More
![Aruba Sunset Sail Experience Aruba Sunset Sail Experience](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/7f/80/0e.jpg)
Aruba Sunset Sail Experience
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Caribbean
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Superb333 reviews4.7
Unwind and end your day on a high note with this relaxing cruise. Climb aboard a comfortable open-de....