Sailing Trips in Caribbean
Top 10 Best Caribbean Sailing Trips
Found 343 Sailing Trips activities in Caribbean. Sort by Popularity. - Page 7Saona Island Tour and Catamaran Party from Punta Cana
Saona Island is like a paradise on earth surrounded by white sand beaches, crystal clear turquoise waters and countless palm trees, this environment invites you to relax. The tour of Saona Island is an experience of a lifetime! T... More
Saona Island Premium Discovery Tour from Punta Cana or Bayahíbe
One of the highest quality Saonas in the area, you will enjoy the privilege of being accompanied by a tour leader. We have limited capacity, and you will have space for your group all the time, guaranteed. Forget about hours aroun... More
Full Day Private Charter (55' Sailing Yacht and up to 12 guests)
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
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Private Tour
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Simply Sailing Private Sail from Sapphire Marina
This is the ideal trip for the true sailor's out there. Enjoy a private 3 hour adventure of straight sailing aboard our beautiful "Robert Perry" designed 40ft Baba pilothouse Cosmos Mariner. Whether you want to learn a few things ... More
Private Tour
Private Catamaran Party with Snorkeling and Unlimited Drink
The first stop is at the reef of Cabeza de Toro beach for an unforgettable snorkeling experience. All necessary and disinfected snorkeling equipment will be provided, always under the supervision of our professional guides. Get in... More
Private Tour
Private Full-Day Catamaran Sailing Charter in St Maarten
Experience some of the finest sailing, swimming and snorkeling in the turquoise waters of St. Maarten. We can alter our trips to meet your needs, that is what we are all about - flexibility. Please discuss your needs with us. We a... More
Private Tour
No1Sxm Private Intimate Day Sail in St. Maarten
Are you ready to go Sailing? True sailing on board of No1Sxm Trimaran: stable, smooth, fast. The 5 hour experience takes you along the south west coast of St.Maarten/Saint Martin & up Anguilla Channel. Included are a stop in... More
Private Tour
Full Day Sail with Max Charters
A day with Max Charters is a unique way to experience the Virgin Islands. We carry fewer passengers than most charter companies in order to provide a more intimate experience. Avoid the crowd and enjoy a relaxing day in the island... More
Private Tour
Grand Cayman Snorkeling and Lunch Excursion
Take it easy in paradise with our Swimmin’, Chillin’, and Grillin’ excursion, a luxurious afternoon tour that blends relaxation and adventure. Perfect for unwinding after other Grand Cayman island tours, this experience com... More
Private Tour
Little Bay Half-Day Sail & Snorkel Adventure
Indulge in an authentic sailing experience on a classic Caribbean "Rum Runner" of yesteryear as Tradition sails to one of Anguilla's hidden treasures, Little Bay. Home to turtles, nesting pelicans, tropic birds and magnificent... More
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
Grace Bay Luxury Catamaran Reef Snorkel Sail
Imagine a blissful snorkel stop in the crystal-clear waters in Turks & Caicos, aboard Lady Grace, a luxury catamaran. As the catamaran gently glides over the turquoise waters, you're surrounded by the breathtaking beauty of the Ca... More
Private Tour
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
Private Tour
1-Hour Paddle Board in Condado Lagoon
Paddle board experience on a tour of the Condado lagoon, where you can appreciate the old historic "Los Hermanos" bridge, the maritime life of our reef in a natural reserve, we can see turtles, manatees, and fish of different spec... More
Private Tour
Sail and Snorkel at Cades Reef
Enjoy the majestic views as you travel down the southern coast of the island. A stop will be made at Cades Reef for the opportunity to snorkel in Antigua's largest reef. Then, time to stop at a beach for lunch and a chance to sw... More
Private Tour
Havana's Sunset Cruise
Get a sense of Havana, Cuba, as you sip a mojito while sailing on an open-deck catamaran in Aruba. Watch the setting sun and learn how to dance to salsa music as you admire one-of-a-kind scenic views of the white-sand beach and cr... More
Private Tour
Montego Bay Private Yacht Tour with Open Bar and Lunch
We are not just offering a cruise. We are offering an escape and tranquility. Our aim is to provide sophistication, outstanding customer service and the most memorable nautical experience of your vacation. ... More
Private Tour
All Inclusive Day Sail
Sailing on Helios in the Virgin Islands can be one of the most memorable days spent on your vacation. The Virgin Islands are a popular destination for sailors, with near-constant trade winds, all-year round high temperatures and ... More
Private Tour
Private Caribbean Snorkeling Cruise At Punta Cana & Sharks, Stingray Encounter
Perfect for both small and large groups. Explore the beauty of Punta Cana's white sands and turquoise blue clear waters in your own upgraded private catamaran adventure. A friendly guide to lead the way, an open bar and a professi... More
Private Tour
Private Day Sail - South Coast of Puerto Rico
Our experienced USCG Captain and crew will make sure you experience the most beautiful and secluded spots of the Jobos Bay National Estuarine Research Reserve (JBNERR) in the comfort and privacy of our 36-foot sailboat fit for six... More
Private Tour