Top Caribbean Sailing Tours

Watch the sunset on the deck of a spacious catamaran off Grace Bay while you enjoy a glass of Champagne on this catamaran sightseeing cruise around Providenciales. This 18-and-over tour allows you to enjoy a sunset like no other 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—it's an ideal option for date night.

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.

Set sail from Aruba for a dinner cruise by catamaran, then watch the sun set into the Caribbean as you drink and dine on deck. Enjoy an open bar throughout the cruise, and nibble local and international fare from a sumptuous, three-course buffet. Take in Aruba’s shoreline scenery and cool sea breezes, then return to Palm Beach as the stars appear over the island.

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.

Sail aboard our unique half day cruise, where you will enjoy a fully guided snorkelling tour of the famous Underwater Sculpture Park. Following a buffet lunch and beverages, you will sail to Flamingo Bay to snorkel over a beautiful reef in a protected marine reserve and afterwards, to relax on a soft, white sandy beach. You may get the chance to see diverse marine life such as stingrays, turtles and eels, as you float through the reserve’s crystalline blue waters. On the way back to port, rum punch and other drinks will be served on our open bar. Admission tickets, drinks and lunch are all included in the tour.

Hop aboard the beautiful sailing vessel Cosmos Mariner for a small group sailing and snorkeling adventure for up to 6 guest max. We'll sail from Sapphire Beach Marina and take you to a spectacular location to snorkel with tropical fish. All snorkeling gear will be provided, and alcoholic beverages and soft drinks will be served on board at no additional charge.

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.

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in small groups of up to 10, ensuring a personalized and high-quality experience for all. The bay boasts a vibrant array of marine life and magnificent Green Sea Turtles. Guests often spot blue tangs, sergeant majors, fairy basslets, yellow snappers, and more! Occasionally, you might encounter rare creatures like squids, seahorses, rays, and manatees. We suggest the morning time slots as the marine life is more active. Receive a complimentary video to commemorate your unforgettable adventure. This Activity is suitable for ages 12 years and above.

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.

This four-hour lunch cruise and snorkeling trip via catamaran is especially designed for cruise-ship passengers on Bonaire for a short time. You’ll sail to the Bonaire Marine Park where you’ll enjoy a guided snorkeling trip with a guide who will keep you safe in the sea. Back on board, relax as you indulge in a delicious lunch and drinks while watching the island scenery drift by.

Welcome aboard, fellow adventurers, to the breathtaking paradise of Jost! Here, amidst crystal-clear waters and gentle sea breezes, lies a world of wonder waiting to be discovered.Relax on stunning beaches and enjoy the vibrant atmosphere at the famous Soggy Dollar Bar, where you can sip on the iconic Painkiller cocktail. Please note that you will need to swim ashore to reach the bar—hence the name "Soggy Dollar!" We will also include other stops, such as Sandy Spit and the Bubble Pool, weather permitting, giving you the chance to explore some of the most picturesque areas in the BVI. Join us for a shared sail that includes a delicious buffet lunch and an open bar to keep you refreshed throughout your adventure. Let’s set sail together and create memories that will last a lifetime!

Watch the sunset and dine on Creole fare aboard a catamaran during this excursion from St. Maarten. Sip drinks from the open bar and munch on complimentary appetizers while the sun sinks below the horizon. Once twilight falls, enjoy a buffet-style Creole dinner, followed by dessert and Caribbean rum. Hit the dance floor to island beats while the boat sails back to the marina.

Explore St. Maarten’s natural landscape away from the crowded beaches on a boat cruise that departs from Bobby’s Marina. To ensure your comfort and a personal experience, the boat crew provide a buffet lunch, open bar, and snorkeling gear. Stops on the itinerary range from top landmarks to secluded snorkeling locations often missed by visitors.

Come enjoy a relaxing Halfday snorkeling trip with us as we cruise along the west coast of Grenada to make our way to the iconic underwater sculpture for a guided tour then over to flamingo bay to see the beautiful corals and reefs. All while enjoying the open bar on board!

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.

Sail into the sunset on your own private cruise by booking this excursion on the Frances Anne for private groups of up to six people. You’ll have the option to jump into the water for a bit of swimming and snorkeling, though you may want to stay on board, where a charcuterie board and alcohol and soft drinks will be served.

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.

ARE YOU READY..!! ADULTS ONLY PARTY cruise, we sail 7 days a week, we can cater for groups of up to 140 persons. Welcome to Party City, Negril's HOT SPOT, LIVE DJ's, Bar, table service restaurant, gift shops and more ALL on the white sands on the FAMOUS 7 MILE BEACH Sail to the Coral Reef for a little snorkeling, get a few pictures of the most beautiful marine fish, then it's off to Rick Cafe, on route we may just spot a few friendly dolphins, they love to play and race the boats... As we dock at Ricks Cafe the land Party carries on, you will have 4 hours of fun with us from you step foot onboard until we drop you back to your awaiting buses, we can't wait to sail with you, whether you are celebrating an event or just chilling with friends and family... we will make your day amazing.... did we mention THE BEST JERK FOOD AROUND all made fresh for your tastebuds to dance to. See you in Jamrock. We also email the night before with reminder of the pick up time

End another day in tropical paradise in perfection on this sunset cruise. Hop on board your trimaran vessel late in the afternoon, just in time to set sail as the sun sinks beneath the horizon. You’ll be served snacks and drinks to enjoy as you admire the views. This is a chilled out small-group activity that’s ideal for couples.

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.

Navigate the seas aboard an authentic sailboat during this 1.5-hour excursion in the Bay of San Juan. This sailboat experience uses only wind power, avoiding noisy motors and crowds. Enjoy views of Old San Juan from a different perspective and sip on beer or sangria as you sail; you may even encounter local wildlife like dolphins.

Head out for a day of snorkeling with this all-inclusive yacht trip. You'll visit two different snorkel spots, USVI St. John National park and nearby coral reefs, and snorkel equipment will be provided. As this is an all-inclusive tour, you won’t need to worry about packing your meals—breakfast and lunch will be served plus free soft drinks and alcohol will be available on board.

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 and spot dolphins and sea turtles swimming and playing around the boat.

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.