Sailing Trips in Caribbean
Top 10 Best Caribbean Sailing Trips
Found 333 Sailing Trips activities in Caribbean. Sort by Popularity. - Page 2Tropical Catamaran Snorkeling, Sailing - Cruise ship Friendly
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
St. John Champagne Sunset Sail with Open Bar & Hors D'oeuvres - Westin
As the sun sets our sails rise, and the champagne flows. Experience a Caribbean sunset and celebrate one of nature’s wonders of color under full sail aboard our 55′ catamaran, Daydreamer. Enjoy a relaxing and romantic sail in ... More
Restless Native Catamaran Sunset & Swizzle Cruise
Start a night out in Bermuda the right way with a 1.5-hour sunset cocktail cruise aboard a 50-foot catamaran. Sunsets in paradise are always great, but they’re even better when you enjoy them out on the water, listening to the s... More
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
San Juan Catamaran Sunset Sail with Drinks Included
Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset lighting. This 2-hour sail aboard a 37ft catamaran sailboat completely powered by the wind is the perfect setting for a romantic momen... More
Tango Caribbean Dinner Cruise
Experience the true Caribbean way on this evening dinner cruise! Guests are treated to an open bar and snacks as the catamaran sails along the coast of St. Martin, capturing the captivating colors of a Caribbean sunset. A Creole b... More
Private Luxury Catamaran Yacht. Full or Half Day Charter - Sail, Beach, Snorkel.
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
Private Tour
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
Private Tour
St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast - Westin
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 Westin on St John, guests board our 55′ catamaran for a truly extra... More
Private Tour
Punta Cana Combo Tour: Snorkeling, Catamaran Cruise & Parasailing
Enjoy a 500 feet high panoramic view of the entire coastline and turquoise waters of Bavaro Beach through an exciting parasailing flight. Relax and spend some time on a doble deck catamaran. Discover the wonders of the sea and enj... More
Private Tour
San Juan Bay Day Sail with Drinks Included
Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying complimentary mimosas, house rum punch, and other drinks in moderation. Take in the panoramic views on this pleasure sightseeing tour of San Juan Ba... More
Private Tour
4-hour snorkel cruise to Underwater Sculptures with boat dogs
This tour is offered in different options for different budgets, please be sure to pick the right one!!! Sail to the world famous Underwater Sculpture Park and enjoy a fully guided snorkeling tour of each of the sculptures. A Lunc... More
Private Tour
Private Catamaran Swim sail snorkel cliff jumping SUP
This is a 3-hour charter up to 15 guests with pick up at the cruise ship terminal in dockyard or Hamilton Harbor. Sailboat can accommodate up to 25 people. There is no better way to explore Bermuda than via a boat. Soak up the s... More
Free Cancellation
Private Tour
(Saving 15% )
Snorkel Cat All Inclusive Adventure - 9:45 am
Snorkel at the National Park in St. John and snorkel at an uninhabited island. This trip is all inclusive. Breakfast, lunch, drinks and snorkel equipment is provided. This adventure includes the captain, crew, sundeck, shade and f... More
Private Tour
Sail Away: Private Scenic Excursion from San Juan
Private, AM. PM. or Sunset, sailing around the San Juan Bay and Harbor of Old San Juan, Puerto Rico. (Prices already include all taxes and fees) This sightseeing, sailing tour will pass historical, Old San Juan Forts and views o... More
Private Tour
Catamaran Cruise, Snorkel, ATV, Horseback Ride and Swim
Gear up for a ride on the wild side on this amazing ATV Quad Safari and discover the real Jamaican backcountry. Journey through the rugged dirt trails of a historic estate; ride under a picturesque bridge that connects the mountai... More
Private Tour
Sunset Sailing Cruise with premium drinks and bites
Our most relaxing trip in our list. Unwind with a drink and some snacks while the sun sets. Step aboard the sailing catamaran and cruise to Spanish Water and Fuik bay. We leave at 5.30 PM and return at 8.00 PM. Book our popular s... More
Private Tour
Punta Cana Small group Adults only Snorkel with Food and drinks
Hispaniola is the only excursion company in the Dominican Republic to have a floating kitchen and a Big floating bar. Yes, you read that right. A floating kitchen where we serve our beloved guests the most exquisite seafood that w... More
Private Tour