Top Caribbean Cruises & Sailing

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.

Get out onto the water and admire sea life on this sailing tour. In the company of a guide, set out on a catamaran and take in views of Aruba’s beaches as you sail. Suit up in snorkeling equipment and swim in the clear water. Visit the marine sanctuary, Catalina Bay, and the Caribbean's largest shipwreck, Antilla. Enjoy island time with an open bar under a shaded canopy as you sail back to shore after your memorable snorkel experience.

Snorkel with sea turtles and unwind on a private beach during this half-day Rose Island boat adventure. Cruise aboard a sleek vessel designed for comfort and perfect photos, whether it’s just you and a partner or a group of up to 20. Swim, snorkel, and soak in the breathtaking beauty of Green Cay and Rose Island. Please note- this is not a private charter.

Sail the waters off Aruba in a 40-foot (12-meter) trimaran on this afternoon tour departing from Palm Beach. Explore the underwater world of coral and tropical fish using the provided snorkel equipment. Learn about the marine environment from the captain and crew as you sip drinks from the open bar and dig into a sandwich lunch.

Easily navigate Turks and Caicos in a 4- or 6-seater golf cart with this one-day rental opportunity. Rather than deal with bulky cars, zip around the island in an open-air golf cart and enjoy the wind on your face. Customize your itinerary to your interests and maximize your time on the islands with your group.

Watch the sunset from the water on a fun “pirate ship” cruise in Aruba. Aboard a swashbuckling-style schooner, enjoy the gentle trade winds, and sip a cocktail from the open bar. Get the chance to admire the island’s scenery from the teak decks as you sail along the coast and take advantage of the onboard rope swing to make a splash.

Sail along the coast of St. Martin during sunset on this excursion. Enjoy snacks, drinks, and entertainment as you take in the exquisite colors of a Caribbean sunset. Pick a spot on the spacious deck of the boat or upfront in the nets stretching between the two hulls of the catamaran to relax, relish the ride and watch the sun sink below the horizon, ending another beautiful day in paradise.

Skip the standard boat tour and enjoy a mimosa brunch experience while sailing across the turquoise waters of Aruba on this unique morning snorkeling cruise. Set sail aboard a custom-built catamaran and drop anchor for three diving stops where you can explore marine life and shipwrecks 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.

Mangroves are one of Bonaire’s most important ecosystems. Discover them with an experienced nature guide on this clear-bottom kayak tour of Lac Bay’s mangroves, with snorkeling gear so you can see even more. Learn about four different species of mangroves and the complex relationship between plants, animals and fish as you paddle. Price excludes marine park fees: these are free for cruise ship passengers and available to purchase for non-cruisers.

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 and enjoy a buffet dinner aboard a catamaran on this evening cruise from Nassau. Take in the views of Paradise Island Harbor, the Atlantis, and the Bahamian sunset.

Visit three Grand Cayman attractions on this tour to Stingray City, the Coral Garden, and a location where you can snorkel with starfish. You'll have the chance to swim near stingrays in their natural environment and enjoy the clear Caribbean waters of the Cayman Islands. Snorkeling gear and transportation from the cruise terminal and hotels in George Town and the Seven Mile Beach area are provided.

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.

Exploring a new food and drink scene can be overwhelming—especially when you don’t know where to go or what’s authentic. This guided rum and food walking tour removes the guesswork by taking you straight to trusted local spots in downtown Nassau. Sample traditional flavors and learn the stories behind them, craft your own cocktail, and learn how Caribbean rum is made at a historic distillery.

Tour Nassau's landmarks and highlights, including a visit to the Atlantis Resort aboard a comfortable minivan. During this 2.5-hour sightseeing tour, huff up the Queen Victoria staircase for spectacular photo ops and visit the Bahamas Rum Cake Factory. Visit the famous Atlantis resort, the Graycliff Chocolate Factory and John Watling's Distillery. Along the way, enjoy historical and cultural commentary from your local guide. Round-trip transportation from the Nassau port or hotels is included.

Immerse yourself in Bermuda's underwater world without getting wet during this 1.5-hour glass-bottom boat cruise. Relax in a comfortable vessel, peering through the boat's glass bottom at the marine activity while listening to your crew's informative commentary. See the seagrass beds where turtles find their lunch, the bustling coral reefs, and the shipwreck of the HMS Vixen.

Getting out on the water is one of the best ways to experience St. Maarten, but arranging a boat day on your own can be complicated and expensive. This fun catamaran cruise from Simpson Bay makes it simple, with a comfortable vessel and planned stops built into the day. Relax on cushioned seating as you journey along the water, then dive in when the catamaran anchors to enjoy snorkeling or stand-up paddleboarding.

Finding a snorkeling experience in Turks and Caicos that balances great reef access with comfort can be tricky, but this half-day catamaran tour from Grace Bay makes it easy. Cruise aboard a spacious double-decker catamaran to colorful reefs near Providenciales, with quality snorkel equipment provided so you can explore the underwater scenery with ease.

Experience the Dominican coast on the back of a horse during this half-day horseback riding tour. Get matched with a horse according to your abilities and get set up with all the necessary safety equipment. All instruction is included, so even beginners can participate. Ride along the beach and take in the sights of the soft sand and blue water; perfect for those frame-worthy vacation photos.

Hop aboard a Can-Am Outlander 450 ATV and experience the best of Nassau during a morning or afternoon tour with a professional local guide. Drive your own ATV and comfortably cruise along the coastline. Learn about the history of the Bahamas and visit historical sites such as Fort Montagu and Fort Charlotte. Then enjoy a beach break to relax and take in the beautiful clear waters.

Aruba is renowned for its underwater wonderlands, but many are impossible to access from the beach. This boat tour takes you to three top snorkel spots, including the Malmok Reefs, Boca Catalina, and the WWII shipwreck. And not only that—sailing on the teak Jolly Pirate ship with bring serious Pirates of the Caribbean vibes, too.

End another great day in paradise with a relaxing sail on the Caribbean Sea just as the sun is setting. Board your vessel and choose a spot on the spacious catamaran to take in the scenic views. Enjoy a drink from the open bar as well as a selection of finger foods while you sail and watch the sky turn from blue to hues of yellows, oranges, and pinks.

Set sail aboard a catamaran and explore the Turks and Caicos Barrier Reef on this half-day excursion. At the reef, you’ll get the chance to snorkel and discover this underwater world. It is known for its diversity of species, including parrot fish, Caribbean reef sharks, and hard and soft coral. Then, spend a relaxing time on an island beach. Hotel pickup is included for added convenience.