Sailing Trips in Caribbean
Top 10 Best Caribbean Sailing Trips
Found 390 Sailing Trips activities in Caribbean. Sort by Popularity. - Page 4Aruba Sunset Sail Dinner Cruise with Open Bar by Catamaran
Included in this three (3) hour sail is a dinner buffet with appetizers, mains and dessert buffet and an open bar with sparkling wine (welcome drink), house wine, cocktail menu, local beer and soda's & juices.... More
Aruba Sunset Sail Dinner Cruise with Open Bar by Catamaran
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Caribbean
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Superb393 reviews4.8
Included in this three (3) hour sail is a dinner buffet with appetizers, mains and dessert buffet an....
Norman Island - The Caves & The Indians - Sailing & Snorkel Tour
***Ideal for hotel/villa Guests*** If arriving by cruise , please book our other Norman Island listing first. You can book this shared sail if the other option is not available. Welcome aboard, fellow adventurers, to the breatht... More
Norman Island - The Caves & The Indians - Sailing & Snorkel Tour
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Caribbean
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Superb19 reviews5
***Ideal for hotel/villa Guests*** If arriving by cruise , please book our other Norman Island list....
Aruba Sunset Sail with Open Bar
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Caribbean
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Exellent379 reviews4.5
With this trip you will sail along Aruba's scenic coastline and enjoy the most spectacular and fun s....
Leisure Full Day Catamaran (Blue, Aqua or LIC)
Crafted Catamarans: Specifically designed for water tours, comfort, spacious decks, shaded seating areas, bar, and restroom for the enjoyment of passengers. Scenic Coastal Routes: Allowing passengers to enjoy the picturesque coas... More
Likely to Sell Out Leisure Full Day Catamaran (Blue, Aqua or LIC)
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Caribbean
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Superb18 reviews4.9
Crafted Catamarans: Specifically designed for water tours, comfort, spacious decks, shaded seating a....
Good Times Too Premium Catamaran Lunch Cruise
Our Lunch cruise on Good Times Too offers limited numbers of passengers of 20 persons. We start from the west coast (not Bridgetown) with the advantage of arriving at the turtle site before the main crowd. Our crew and staff provi... More
Likely to Sell Out Good Times Too Premium Catamaran Lunch Cruise
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Caribbean
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Superb215 reviews4.9
Our Lunch cruise on Good Times Too offers limited numbers of passengers of 20 persons. We start from....
Tropical Catamaran Snorkeling, Sailing And Beach Experience
Join us for a 6 Hours yachting, sailing, and snorkeling experience. Your comfort and safety are our main concern. We will do an easy South side Coastal sailing French Side, Dutch Side with 2 or more stops for snorkeling, beach t... More
Likely to Sell Out Tropical Catamaran Snorkeling, Sailing And Beach Experience
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Caribbean
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Superb285 reviews4.8
Join us for a 6 Hours yachting, sailing, and snorkeling experience. Your comfort and safety are ou....
3 hour Glow Worm Sunset Cruise from Providenciales
Watch the bioluminescence of glow worms on a spectacular sunset cruise from Providenciales! For a few evenings after the full moon each month, the waters of Caicos Banks play host to this natural phenomenon, when thousands of glow... More
Likely to Sell Out 3 hour Glow Worm Sunset Cruise from Providenciales
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Caribbean
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Superb148 reviews4.6
Watch the bioluminescence of glow worms on a spectacular sunset cruise from Providenciales! For a fe....
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
Likely to Sell Out Iconic Aruba Sail and Snorkel Experience
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Caribbean
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Superb430 reviews4.8
Experience the joy of sailing along Aruba’s stunning beaches on a spacious catamaran & snorkelingÂ....
Sunset & Champagne Cruise on a Classic Schooner with boat dogs
...the perfect ending to another perfect day. Sail just offshore of the coast of Grenada. Enjoy a glass of champagne, fresh Appetizers from the onboard chef and cold drinks from our open bar while taking in the remarkable view of... More
Likely to Sell Out Sunset & Champagne Cruise on a Classic Schooner with boat dogs
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Caribbean
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Superb167 reviews4.8
...the perfect ending to another perfect day. Sail just offshore of the coast of Grenada. Enjoy a g....
St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max
An Unforgettable Sailing Experience! We offer a Semi-private and all inclusive Day trip that will be the best day of your vacation. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us as we e... More
Likely to Sell Out St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max
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Caribbean
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Superb637 reviews4.9
An Unforgettable Sailing Experience! We offer a Semi-private and all inclusive Day trip that will be....
Punta Cana Private Catamaran Cruise: Snorkeling, Beach & BBQ
This private catamaran tour in Punta Cana combines adventure, relaxation, and VIP exclusivity in one unforgettable experience. Unlike shared tours, this all-inclusive cruise is reserved just for your group—giving you full access... More
Private Tour
Likely to Sell Out Punta Cana Private Catamaran Cruise: Snorkeling, Beach & BBQ
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Caribbean
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Superb39 reviews4.6
This private catamaran tour in Punta Cana combines adventure, relaxation, and VIP exclusivity in one....
Private Tour
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
Private Tour
Likely to Sell Out Restless Native Catamaran Sail and Snorkel Tour
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Caribbean
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Superb940 reviews4.9
Get the most out of your time in Bermuda with a 3.5-hour sail on a pink catamaran. Your captain make....
Private Tour
Hakuna Matata - St Maarten Catamaran day cruise
Enjoy a relaxed day perfect for families (kids welcome!), couples, and groups. Captain Robert, with years of experience sailing the world’s oceans, shares captivating stories above and below the surround water. We pride ourselv... More
Private Tour
Likely to Sell Out Hakuna Matata - St Maarten Catamaran day cruise
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Caribbean
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Superb79 reviews4.7
Enjoy a relaxed day perfect for families (kids welcome!), couples, and groups. Captain Robert, with ....
Private Tour
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
Private Tour
Likely to Sell Out Chill and Grill Catamaran Tour in Bonaire
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Caribbean
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Superb573 reviews5
With our Catamaran, we will sail along the beautiful coast of Bonaire and Klein Bonaire. We will sto....
Private Tour
Two islands, One paradise
Sailing between St Kitts and Nevis is a totally unique experience. The trade winds constantly blow, and our route along the leeward side of St Kitts gives us flat water and constant breeze, Ideal sailing conditions. Come and see t... More
Private Tour
Likely to Sell Out Two islands, One paradise
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Caribbean
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Superb5 reviews5
Sailing between St Kitts and Nevis is a totally unique experience. The trade winds constantly blow, ....
Private Tour
Luxury Lagoon Cruise with Onboard Chef and Signature Cocktails
The Luxury Lagoon Cruise allows you to cruise along Aruba’s Southern Coast aboard our Teak Schooner. While cruising, join us by the bar for a cool refreshment or lay down on one of our lounges to unwind and take in the sight. So... More
Private Tour
Likely to Sell Out Luxury Lagoon Cruise with Onboard Chef and Signature Cocktails
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Caribbean
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Superb243 reviews4.8
The Luxury Lagoon Cruise allows you to cruise along Aruba’s Southern Coast aboard our Teak Schoone....
Private Tour
Days End Sunset Sail from the Westin at Frenchman's Reef
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
Private Tour
Likely to Sell Out Days End Sunset Sail from the Westin at Frenchman's Reef
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Caribbean
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Superb34 reviews4.6
Step aboard the Flying Frenchman, our newly designed, state-of-the-art, luxury sailing catamaran for....
Private Tour
Private Angelfish Snorkeling with Brunch in Aruba
You are cordially invited to indulge yourself in the privacy and comfort of an Aruba sailing charter! Whatever your desires, the crew of the Tropical Sailing will provide you with the memory of a lifetime! This boat charter is pri... More
Private Tour
Likely to Sell Out Private Angelfish Snorkeling with Brunch in Aruba
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Caribbean
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Superb2 reviews5
You are cordially invited to indulge yourself in the privacy and comfort of an Aruba sailing charter....
Private Tour
Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)
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
Private Tour
Likely to Sell Out Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)
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Caribbean
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Superb139 reviews5
The Virgin Islands are the sailing capital of the world!! Sail with us from St. Thomas to the exotic....
Private Tour
Small Group Snorkeling, Sharks & Rays Encounter At Punta Cana
Spend an unforgettable day on the water with this 3-hour by small boat and reef adventure from Punta Cana. Get up close and personal with the Caribbean’s rich marine life without having to get wet. Marvel at gorgeous schools of ... More
Private Tour
Likely to Sell Out Small Group Snorkeling, Sharks & Rays Encounter At Punta Cana
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Caribbean
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Very Good82 reviews4
Spend an unforgettable day on the water with this 3-hour by small boat and reef adventure from Punta....
Private Tour