Top Caribbean Sailing Tours

End your week in Curacao with a relaxing sunset sail from Willemstad. Board your catamaran and sail into the sunset, while you much on light snacks and sip on provided beverages. Take in the sights of the island as you cruise up the east coast, Caracas and Fuik bays, and around the waterfront of Spanish Water.

Exploring Bermuda's coastline can be tricky without a boat of your own, but this evening cruise keeps things simple. Head out onto the water to enjoy the sunset from a unique vantage point aboard a 50-foot (15-meter) catamaran, then return to land with plenty of time to enjoy the rest of your evening. While onboard, sip on classic Bermudian rum cocktails and enjoy the sounds of island music—a truly relaxing experience in paradise.

Visit Saona Island, an idyllic speck of sand and palm trees in the blue Caribbean, during a full-day tour from Punta Cana. Board a small speedboat for the thrilling ride out to the island, including a stop at a natural swimming pool where you can see starfish. Upon reaching Saona Island, spend the day exploring; stroll along the beach, relax in the white sand and swim in the azure waters. Sip drinks from the open bar and enjoy a buffet lunch of traditional Dominican fare. Round-trip transportation from Punta Cana is included.

Sail to Isla Icacos on this full-day cruise from Fajardo aboard a modern 51 ft. sailing catamaran. Relax and enjoy the scenery as you travel, then snorkel among reefs teeming with tropical fish and spend time on the beach. Midday, enjoy a sandwich buffet lunch with beverages included. Hotel pickup and drop-off from San Juan, Condado, and Isla Verde areas are provided for convenience.

Sail the Caribbean waters on a luxurious catamaran and stop to snorkel on the way to Nevis' Pinney's Beach. During this full-day tour from St. Kitts, enjoy hospitality and guidance from your friendly captain and crew. In a secluded cove, don the provided snorkel equipment and jump in. Eat lunch onboard and sip drinks from the open bar. Explore the white sand, relax, and swim before returning to St. Kitts.

Discover the underwater wonderlands of Cap Cana during an excursion that combines swimming, sailing, and snorkeling in the warm waters of the Caribbean Sea. You'll discover nature-rich spots that are only accessible by boat and increase your chances of spotting of tropical marine life. Plus, unlimited access to an open bar plus a seafood dinner at a floating kitchen are included.

Enjoy an afternoon of fun in the sun and sea, topped off with a barbecue of grilled seafood. Sail on a comfortable catamaran around the sparkling coastline of Bonaire and Klein Bonaire islands, stopping at the Bonaire Marine Park to snorkel with a guide. Sail to another pretty spot for more water play while your crew prepares your tasty feast on board. Return to port as the sun is setting on a glorious day.

The island of Jost Van Dyke is a beautiful place to spend a day on the sand, but many tours depart later in the morning, which means less time on the island. This catamaran excursion gets you out to sea bright and early, with a stop along the way for swimming and snorkeling.

Take in stunning views of the Caribbean with this luxurious half-day cruise in Barbados. You won't have to worry about a drink tab—an open bar comes with your package. Relax aboard a double-decker pontoon boat for unobstructed views of the water. Unlike more crowded options, this cruise offers a small-group setting.

Get access to the National Wildlife Marine Refuge on a sailing yacht during this half-day tour from Charlotte Amalie. Learn about the turtles' behavior and habits through guided commentary and watch them munch on sea grass before sailing out to Buck Island, where you can swim and snorkel to explore the underwater world. This convenient tour combines two of the most popular water activities in a single booking.

Spend the day on your own 50' Luxury Catamaran Yacht. This price is all inclusive for the Yacht, up to 12 guests. You can select a half or full day charter. Visit the islands of St. Thomas, St. John and surrounding cays. SY Sirena is a 50′ Luxury catamaran with a spacious salon that opens on to an expansive back deck with seating and dining. The bow of the boat offers relaxing seating with bean bag chairs and large trampolines for group conversations, tanning or intense turtle, dolphin watching. There are plenty of water toys to keep you entertained, from snorkeling equipment to relaxing floats. Price includes ice, soda, beer and rum punch. You and our captain will design an itinerary that best meets the needs of your group. *Please note the BVI is not available on this vessel, but a visit to the BVI can be booked under Product Codes 111649P24 or 111649P25. Departure from American Yacht Harbor in Red Hook; pickup from Cruz Bay, STJ possible with advance request after booking.

Cruise around St. Maarten with stops at Tintamarre, Creole Rock, and Grand Case on this full-day sailing excursion. Explore the lovely natural beauty of Tintamarre, then head to Creole Rock for some of the island's best snorkeling. Lunch is then served on board. Cruise down the coast after lunch and sail down pass Marigot, Low Land with a stop at Long Beach for our Floating Bar. Sunset sail back with our festive crew.

Swim with green and hawksbill sea turtles on a sailing adventure from St. Thomas to Maho Bay, St. John, and Honeymoon Beach, St. Thomas. You'll make two snorkeling stops on your voyage, with a picnic lunch served on board in between. After swimming, enjoy free alcoholic beverages from the on-board bar. Note that onsite parking at the Ritz-Carlton now costs $30. Bring your own towel to help conserve the island's fresh water.

Parasail 500 feet (150 meters) above the coast of Punta Cana, then go snorkeling off a party boat during this thrilling excursion. Don a safety harness and ascend into the sky, getting panoramic views of the spectacular Dominican coastline. Then, board a catamaran and set sail for a local snorkeling spot, diving in to swim with tropical fish among coral reefs. Sip drinks from the onboard open bar and stop at a natural swimming pool for a relaxing dip in the warm water. All equipment, snacks, drinks, and round-trip transportation from Punta Cana are included.

Explore Aruba’s coast on this morning sailing trip. Board a catamaran limited to fewer than 35 guests and unwind as the captain and crew take you to Boca Catalina Beach. Enjoy snorkeling, swimming, and paddling, or simply soak up the sun. All these activities build up an appetite, so enjoy snacks, drinks, and a BBQ lunch onboard. Perfect for anyone looking to escape the mainland for a short while.

Watch the sun set from the deck of a catamaran during this 2-hour champagne cruise from Philipsburg. Sip unlimited champagne and enjoy delectable appetizers while you sail down the coast of St Maarten towards Long Bay. Say goodbye to another day in paradise as the sun sinks below the horizon.

Visit Saona Island, the reef at Catuano, and the Las Palmillas natural swimming pool in a single tour on this catamaran cruise from La Romana. Squeezing all of these stops into a single day is a tough task, but passengers will enjoy lounging on the decks of the catamaran and watching the scenery while the boat whisks them around the island. lunch on the boat and open bar complete this all-inclusive experience.

No need to suffer through a stale packed sandwich on this full-day snorkeling cruise. Instead, enjoy freshly-made pizzas from the unique floating food boat Pizza Pi. Spend the rest of the day working up an appetite with swimming and snorkeling at picturesque beaches and offshore cays. When you’re tired from all that swimming, relax on deck and make the most of the free snacks and open bar.

Embark on a catamaran cruise on the turquoise waters off Punta Cana with other families for a fun day on the water. Everything is taken care of for you: use of snorkeling equipment for both kids and adults, as well as lunch (kids menu available) on board the boat and convenient round-trip transportation from your hotel.

Spend a memorable sunset sailing into the waters around St. John on this cruise from the Ritz-Carlton in St. Thomas. You’ll be treated with refreshing beverages while you sail, with plenty of time to take photos or just enjoy nature’s light show as the sun sets below the Caribbean horizon.

Make a day trip to Jost Van Dyke from St. John that maximizes your time, combining several activities in one excursion. Enjoy a light continental breakfast during the cruise, go for a morning snorkel near the coral reefs surrounding the island, and relax at White Bay beach near the famous Soggy Dollar Bar with a full open bar available on the return cruise.

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 beach are just the start of your day, we set sail for the coral reef, where you get to snorkel if you wish, view the beautiful marine life of Negril, after about an hour we sail to Ricks Cafe, watch as the cliff jumpers wow you with their show and skills, with a Dj and band depending on the day, you can party your day away, then after all that we still get to sail back on the sunset, with a rum punch in hand or an ice cold Red Stripe watch as the Sunset on your most amazing day ALL GUESTS - Will also be able to have a little shopping stop included and get 20% off at the store

Enjoy picture-perfect views on an Aruba sunset cruise followed by our custom seafood dinner at a waterfront restaurant. Set sail aboard a catamaran for a cruise on the Caribbean while you take in the vivid colors of a tropical sunset. Enjoy snacks and an open bar before enjoying our custom dinner served seaside with a glass of wine at the Pelican Nest Restaurant.

Enjoy views of Aruba you can’t get on land during this morning or afternoon cruise. Unlike on big party boats, the vessel accommodates a small group, so everyone can spread out and enjoy some peace and quiet. Use the provided snorkeling gear to explore the underwater world, then refuel with a tasty lunch or dinner, with various options. Afternoon cruises can watch the sunset, too.