Top Caribbean Cruises & Sailing

Sail aboard a luxury catamaran on this sunset cruise from Aruba. During this evening excursion, enjoy tropical cocktails as the sun dips below the horizon and the stars appear. Cruise up Aruba's stunning coastline and enjoy views of Palm Beach while snacking on complimentary appetizers. Get to know the boat's crew as it entertains you with storytelling, local music, and dancing.

Enjoy a new perspective on Old San Juan—and soak up Caribbean breezes and sunset views—aboard this evening boat tour. Following pickup at select local hotels, hop aboard the boat and find a comfortable seat on the deck. Then, spy highlights like Paseo De La Princesa, La Fortaleza, the San Juan City Walls, and more, all while the sun goes down. Light refreshments and alcoholic drinks are available on board.

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.

Enjoy free-flowing Champagne with breakfast and lunch while sailing across the turquoise waters of Aruba. This snorkeling cruise aboard a custom-built catamaran includes three stops where you can explore marine life in the crystal-clear waters. Be charmed by Caribbean music and sea breezes as you sip your mimosa while lounging on the boat — it's perfection in paradise.

Live out your island castaway fantasies aboard a luxury catamaran as you visit the deserted tropical island of Cayo Icacos from San Juan on this half-day sailing cruise. Sail into the aquamarine waters of the Caribbean, admiring views of the El Yunque mountains in the distance, before arriving at the nature preserve of Icacos for a leisurely day of swimming, snorkeling, lunch, and rum cocktails.

Cruise to Dunn's River Falls aboard a catamaran on this 3.5-hour excursion. Sail to a snorkeling location to swim among live coral reefs and schools of tropical fish. Dig in to a beachside buffet of traditional Jamaican food accompanied by an open bar. At Dunn's River Falls, climb the terraced falls to the top, accompanied by your local guides, for views of the surrounding countryside. Lunch, open bar, snorkel gear and round-trip hotel transportation are included. Not available for clients from Carnival Corporation.

Watch the tropical Aruban sunset from aboard a 40-foot (12-meter) trimaran on this happy hour sunset cruise. Depart from Palm beach with an attentive captain and crew; relax on board while sipping drinks from the open bar and munching appetizers. Get your camera ready for the colorful sunset and feel free to ask questions about the area and the marine environment.

Be sure to come hungry for the VI Cat's Harbor Lights Dinner Sail! This catamaran's dinner has offerings for all pallets in front of an award-winning backdrop. And then admire Charlotte Amalie's Harbor lights from the decks of 'the Cat' on this 2-hour barbecue cruise. Get comfortable aboard the 54-foot (16-meter) catamaran as you sail through the harbor, sipping a drink from the open bar.

Watch the sunset from the best possible vantage point—the deck of a boat cruising around St. Thomas—on this evening tour. Get views of the St. Thomas coastline and the outer keys while sipping cocktails and munching on provided appetizers. Enjoy the scenery, snap photos, and be back to shore in time for dinner.

Dance to reggae rhythms and enjoy the cool blue Caribbean on this ‘floating party’ catamaran cruise, including stops to snorkel at a protected reef and join the lively scene at Margaritaville. Back on board, a DJ, unlimited drinks from the open bar, and Jamaican-style appetizers keep the energy going as you soak up stellar views of the island’s north coast. 

Sail the calm, azure waters of San Juan Bay at sunset during a cocktail cruise. Enjoy a warm welcome aboard from your friendly captain and crew, then settle in for a scenic ride. Watch the island coastline glide by as the sun sinks toward the horizon. Sip a complimentary rum punch or sparkling wine with your family and friends and listen as your captain points out landmarks like El Morro Fort and San Juan Gate. Arrive back at the dock in time to continue your evening in San Juan.

Rather than get tired of kayaks and stand up paddleboards, enjoy a more relaxing way to explore the Condado Lagoon aboard a water bike. Stroll safely around the lagoon with the company of an exclusive guide and learn about the rich ecosystem. Keep your eyes peeled for marine animals including manatees, turtles, various species of fish, and even dolphins.

At sunset, the Caribbean’s warm breezes complement stunning views. Take in the experience aboard a 54-foot catamaran sailboat complete with appetizers and alcoholic and non-alcoholic beverages. The trip is ideal for families, couples, and groups. You’ll return to the Marriott's Frenchman's Cove Dock in time for dinner.

Go on an island excursion, and see some of the most popular spots in Aruba on this tour taking off from Oranjestad. Travel the whole island, and see the California Lighthouse, the Ayo Rock Formation, and the Casibari Rock Formations. Visit one of the world’s oldest aloe-vera factories, as well as a 75-year-old, family-run bar. Learn about Aruba’s gold-rush era at the Bushiribana gold mill ruins, and swim in a man-made lagoon at Baby Beach.

Enjoy picture-perfect views on an Aruba sunset cruise followed by a 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 a steak, chicken, or fresh fish dinner served seaside with a glass of wine at the Pelican Nest Seafood Grill.

St. Lucia’s towering peaks and gorgeous coastline mean exploring is best done by land and water. You’ll do both on this full-day tour covering the island’s top highlights, from the ‘Drive-In Volcano’ to mud baths, bathing in Toraille Waterfall, a Pitons photo stop, snorkeling, a bat cave, fishing villages, and more. An included lunch features the distinctive flavors of St. Lucian cuisine for a full cultural immersion.

Go sailing and watch the sunset on a cruise from San Juan. Get great photo ops of Puerto Rico’s coastline and enjoy a comfortable sail on the Caribbean Sea. Your captain shares commentary about the region and provides complimentary drinks for your group of no more than six people.

Maximize the fun in your Punta Cana vacation with an exclusive catamaran party cruise. You can choose between a morning and afternoon departure time, and customize the tour based on your preferred route. Admire Punta Cana’s white-sand beaches, snorkel among tropical fish, enjoy unlimited drinks from the open bar, and dance to local music. Convenient round-trip transportation from your hotel allows you to focus on having a great time.

Cruise around St Lucia aboard a catamaran named 'Tout Bagay' during this 8-hour excursion. With an expert captain and crew as your hosts, spread out on the deck for some sun and relaxation while sipping rum drinks from the open bar. Go ashore to explore sites like Morne Coubrail Estate (where you can opt to go ziplining), the sulphur springs, Toraille Waterfall and the quaint town of Soufriere. Use the provided snorkel equipment to explore the underwater world in Anse Cochon and Marigot Bay. Enjoy a Creole-style buffet and round-trip transportation from your hotel.

Set sail across the Caribbean on this 1.5-hour cruise from San Juan and enjoy unforgettable views of the Puerto Rican capital. Hop aboard a traditional sailboat and sip complimentary drinks as you cruise along the coast. Keep your camera to hand as you pass landmarks like San Juan Bay Marina and El Morro Fort, and spot dolphins and sea turtles swimming and playing around the boat.

Explore the waters around Aruba aboard a 65-foot (20-meter) catamaran, the 'Arunsun'. During your cruise, relax on the spacious deck and enjoy hospitality from your friendly captain and first mate. Find a spot in the sun, the shady back end of the boat, or in the nets up front. Enjoy snacks and drinks from the open bar. Stop to snorkel at the Antilla Shipwreck and Catalina Bay using the complimentary snorkel equipment.

Cruise the west coast of Barbados for a day on a 60-foot (18-meter) catamaran. You’ll make two or three stops where you can dive in and experience life under the sea at premier snorkeling spots, including a shipwreck. Swim among the tropical fish, vibrant corals and possibly turtles and other marine life. Choose between either a three- or five-hour excursion. Unlimited drinks and a light breakfast are included, as well as lunch on the five-hour cruise.

Explore the waters around St. Maarten on a 6-hour speedboat tour. Avoid the cruise ship crowds and visit both the Dutch and French sides of the island in a family friendly, small group setting, which includes five stops to see different aspects of the marine environment. You’ll swim and snorkel in a sea turtle habitat, sting rays and tropical fish on uninhabited islands. Sunbathing on some of the finest white sand beaches the Caribbean has to offer while feeling the rush of commercial jets landing directly over your head at the famous airport. Along the way, your captain will share entertaining and engaging commentary and you’ll sip drinks and indulge in unlimited snacks, all included in the price.

Watch the sunset on the deck of a spacious catamaran off Grace Bay while you enjoy a glass of Champagne. This 18-and-over tour, which includes hotel pickup and drop-off, allows you to enjoy a spectacular sunset while rocking gently on the Caribbean waters. Dine on snacks, including fresh conch fritters, provided by a local restaurant while you toast the gorgeous surroundings with wine, Champagne, rum punch, or soft drinks.