Sailing Trips in Caribbean
Top 10 Best Caribbean Sailing Trips
Found 410 Sailing Trips activities in Caribbean. Sort by Popularity. - Page 4St Kitts Full Day Catamaran to Nevis
Board your Catamaran for the sailing, snorkeling and beach experience you will never forget! Snorkel in a secluded cove, with all equipment supplied, and attentive crew to ensure the best experience. Enjoy the included open bar an... More
St Kitts Full Day Catamaran to Nevis
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Caribbean
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Superb424 reviews4.8
Board your Catamaran for the sailing, snorkeling and beach experience you will never forget! Snorkel....
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 charters. After checking in at the Ritz-Carlton on St. Thomas, guests board our 55′ catamaran for a tr... More
St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast....
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Caribbean
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Superb49 reviews4.8
This one of a kind excursion to Jost Van Dyke allows passengers to spend the most time on the island....
Half Day Snorkeling Trip in Grenada
Come enjoy a relaxing Halfday snorkeling trip with us as we cruise along the west coast of Grenada to make our way to the iconic underwater sculpture for a guided tour then over to flamingo bay to see the beautiful corals and reef... More
Half Day Snorkeling Trip in Grenada
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Caribbean
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Superb26 reviews5
Come enjoy a relaxing Halfday snorkeling trip with us as we cruise along the west coast of Grenada t....
Che’s snorkel catamaran! turtles & shipwrecks (semi private)
(Small group) We are the only catamaran that sails early to avoid the crowds of commercial tours. That’s our niche! Che’s snorkel focused trip has a laid back, personal feel. customized to suit you with only 10 guests. Check ... More
Che’s snorkel catamaran! turtles & shipwrecks (semi private)
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Caribbean
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Superb448 reviews5
(Small group) We are the only catamaran that sails early to avoid the crowds of commercial tours. Th....
Punta Cana Booze Cruise, Snorkeling, Bar Entertainment Open Bar
Unforgettable Party Experience Aboard in your Punta Cana boat adventures! Set sail for a one-of-a-kind adventure on the Caribbean Sea! Join us aboard your vibrant, high-energy Punta Cana party boat for an unforgettable day of sun,... More
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Punta Cana Booze Cruise, Snorkeling, Bar Entertainment Open Bar
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Caribbean
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Exellent57 reviews4.4
Unforgettable Party Experience Aboard in your Punta Cana boat adventures! Set sail for a one-of-a-ki....
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Catamaran Sunset Sail
You are on course for a good time with Bermuda's original sunset Sail. Soak up the setting sun and sensual seascapes as we sail in paradise, with entertaining, discussion-style commentary and island music as you sail through the G... More
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Catamaran Sunset Sail
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Caribbean
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Superb49 reviews4.6
You are on course for a good time with Bermuda's original sunset Sail. Soak up the setting sun and s....
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Punta Cana Exclusive Adults-Only Snorkel with Food and Drinks
Only company with a floating kitchen and large floating bar Our menu options cater to all tastes! Coral museum and interpretation center upon arrival Snorkeling area: renowned for having the most vibrant marine life in the regi... More
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Punta Cana Exclusive Adults-Only Snorkel with Food and Drinks
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Caribbean
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Superb510 reviews4.9
Only company with a floating kitchen and large floating bar Our menu options cater to all tastes! ....
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Day Sail without transportation
First, we sail to the paradise Island of Icacos aboard the modern, 51 ft. sailing catamaran, SPREAD EAGLE II!  The brisk 40 to 50-minute sail to the protected anchorage off of this uninhabited Spanish Virgin Island is beautifu... More
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Day Sail without transportation
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Caribbean
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Superb86 reviews4.8
First, we sail to the paradise Island of Icacos aboard the modern, 51 ft. sailing catamaran, SPRE....
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Grace Bay Luxury Catamaran Reef Snorkel Sail
Imagine a blissful snorkel stop in the crystal-clear waters in Turks & Caicos aboard a luxury catamaran. As the catamaran gently glides over the turquoise waters, you're surrounded by the breathtaking beauty of the Caribbean. The ... More
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Grace Bay Luxury Catamaran Reef Snorkel Sail
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Caribbean
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Superb12 reviews5
Imagine a blissful snorkel stop in the crystal-clear waters in Turks & Caicos aboard a luxury catama....
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SUNSET PARTY CATAMARAN Ricks Cafe ADULTS ONLY DJ Montego Bay
LETS PARTY...!!! STRICTLY OVER 18's From pick up to drop off, enjoy the ONE LOVE vibes Bob Marley sings about When arriving at the departure area of NEGRIL 7 MILE, the party starts, with DJ's playing and fun and games on the beac... More
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SUNSET PARTY CATAMARAN Ricks Cafe ADULTS ONLY DJ Montego Bay
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Caribbean
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Superb12 reviews5
LETS PARTY...!!! STRICTLY OVER 18's From pick up to drop off, enjoy the ONE LOVE vibes Bob Marley s....
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San Juan Bay Private Tour with Drinks and Tapas: 4+ people
Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choice between a 37 foot sailboat ot a a high performance Powerboat. Enjoy complimentary local drinks. Your personal tour guide and Pro ... More
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Private Tour
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San Juan Bay Private Tour with Drinks and Tapas: 4+ people
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Caribbean
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Superb47 reviews5
Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choice....
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Private Tour
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Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten
Our Captain has 25+ years of experience, 0 incidents and is super helpful. He loves to tell amazing stories and will keep you entertained with his great energy. Our business is family owned, super friendly, warm and cozy kid frie... More
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Private Tour
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Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten
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Caribbean
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Superb475 reviews5
Our Captain has 25+ years of experience, 0 incidents and is super helpful. He loves to tell amazing ....
Free Cancellation
Private Tour
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Iconic Aruba Sail and Snorkel Experience
Experience the joy of sailing along Aruba’s stunning beaches on a spacious catamaran & snorkeling at the marine sanctuary, Catalina bay, and the famous Antilla shipwreck. This tour is not only highly rated, but is also recogniz... More
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Private Tour
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Iconic Aruba Sail and Snorkel Experience
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Caribbean
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Superb482 reviews4.8
Experience the joy of sailing along Aruba’s stunning beaches on a spacious catamaran & snorkelingÂ....
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Private Tour
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Jolly Pirate Sunset Grub and Grog Dinner Sail in Aruba
Join the Jolly Crew aboard Aruba's liveliest sunset party cruise with an opportunity to swing from the Jolly Pirate yard arm. There's a DJ aboard and a tasty BBQ is served as the sun dips down past the horizon. Our floating happy ... More
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Private Tour
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Jolly Pirate Sunset Grub and Grog Dinner Sail in Aruba
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Caribbean
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Superb57 reviews4.9
Join the Jolly Crew aboard Aruba's liveliest sunset party cruise with an opportunity to swing from t....
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Private Tour
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The Original Eco Tour Full-Day Around the Island of Sint Maarten
Enjoy a full day sailing aboard Too Rhum Punch or Quality Time our friendly comfortable and Fun Catamaran around the island of Sint Maarten / St Martin. This tour offers a stop at the best 2 snorkeling venues  in the French Natu... More
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Private Tour
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The Original Eco Tour Full-Day Around the Island of Sint Maarten
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Caribbean
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Superb558 reviews4.9
Enjoy a full day sailing aboard Too Rhum Punch or Quality Time our friendly comfortable and Fun Cata....
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Private Tour
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Likely to Sell Out
Two Islands, One Paradise: Full-Day Catamaran from Port Zante
Sail between St. Kitts and Nevis aboard 65-foot catamaran Swaliga in a relaxed, spacious setting capped at 40 guests for comfort. This is not a crowded party boat - there is room to move, unwind, and enjoy open-deck views. Our ro... More
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Likely to Sell Out Two Islands, One Paradise: Full-Day Catamaran from Port Zante
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Caribbean
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Superb42 reviews4.9
Sail between St. Kitts and Nevis aboard 65-foot catamaran Swaliga in a relaxed, spacious setting cap....
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Private Tour
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Likely to Sell Out
Aruba Afternoon Snorkel Sail aboard Palm Pleasure Catamaran
Experience Aruba's magical marine life as you set sail aboard a spacious catamaran and snorkel at two spectacular locations. A friendly crew will take you snorkeling around the historical Antilla shipwreck, the largest and most fa... More
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Likely to Sell Out Aruba Afternoon Snorkel Sail aboard Palm Pleasure Catamaran
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Caribbean
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Superb311 reviews4.6
Experience Aruba's magical marine life as you set sail aboard a spacious catamaran and snorkel at tw....
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Private Tour
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Likely to Sell Out
Half Day Private Sailing Catamaran and Snorkel Trip to St John
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
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Private Tour
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Likely to Sell Out Half Day Private Sailing Catamaran and Snorkel Trip to St John
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Caribbean
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Superb100 reviews5
Sail with Liberty guests experience real sailing on our spacious, private catamaran. We sail you to ....
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Private Tour
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Likely to Sell Out
Chill and Grill Catamaran Tour in Bonaire
With our Catamaran, we will sail along the beautiful coast of Bonaire and Klein Bonaire. We will stop for our first snorkel experience somewhere in the Bonaire Marine Park, our professional guide will lead you into the water to di... More
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Private Tour
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Likely to Sell Out Chill and Grill Catamaran Tour in Bonaire
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Caribbean
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Superb624 reviews5
With our Catamaran, we will sail along the beautiful coast of Bonaire and Klein Bonaire. We will sto....
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Private Tour
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Likely to Sell Out
St. John PiZZA Pi Snorkel Sail with Beach Stop, Lunch & Open Bar - Westin
Join us aboard one of our luxury catamarans, as we set sail for the best snorkeling destinations surrounding St. John. Start the day with a sail to an offshore cay for premier snorkeling. In addition to fruit, salads, and cookies,... More
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Private Tour
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Likely to Sell Out St. John PiZZA Pi Snorkel Sail with Beach Stop, Lunch & Open Bar ....
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Caribbean
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Superb162 reviews4.9
Join us aboard one of our luxury catamarans, as we set sail for the best snorkeling destinations sur....
Free Cancellation
Private Tour
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