Top Caribbean Sailing Tours

Set sail along the coast of St. Croix and take in the Caribbean sunset on this cruise package. Relax onboard a catamaran as live music sets the mood, whilst enjoying complimentary rum punch, soda, and filtered water. Travel past the historic Frederiksted waterfront and the Sandy Point National Wildlife Refuge on this gentle boat trip. A great way to unwind at the end of a busy vacation and take in the island’s natural splendor.

Set sail aboard a catamaran and explore the Turks and Caicos Barrier Reef on this 4.5-hour half-day excursion. At the reef, you’ll snorkel among diverse species including parrot fish, Caribbean reef sharks, and hard and soft coral. Then, spend a relaxing time on an island beach. This tour offers a picnic lunch and a full open bar after snorkeling for a complete experience.

Relax and enjoy the views on this sunset cruise off Aruba’s spectacular coastline. Board a 45-foot (15-meter) catamaran equipped with spacious decks, trampolines for sunbathing, and a large roof for shade. There’s also an open bar on board to add to the island vibe. The catamaran can accommodate up to 42 passengers in total. Bookings over 15 passengers can be done by making multiple bookings.

Climb aboard the catamaran "The Phoenix" for a shared half-day sail around the sights of Sint Maarten. Explore the warm Caribbean Sea with ease with the supplied water gear, for a day of swimming, snorkeling, paddleboarding, or relaxing. Indulge in fresh fruit, pound cake, and a freshly prepared lunch alongside refreshing cocktails, beer, and non-alcoholic beverages. Finish the day watching the planes take off as you sail past Maho Beach—a must-do when visiting the island (weather permitting).

Spend some time in Aruba’s spectacular marine environment on this multi-activity catamaran cruise. Sail aboard "The Dolphin" and lounge on the deck of the boat, then dive in and explore the reef and the shipwreck “Antilla” on two snorkel stops. You’ll learn about the local flora, fauna, and history through guided commentary and enjoy a light lunch between activities.

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.

Adventurous outdoor-lovers will enjoy this yachting, sailing, snorkeling, and swimming experience during this 6-hour tour. We'll head to the south of the island to sail on the French and Duch sides taking a few stops for snorkeling, swiming and spotting the planes on the famous Maho Beach. Prepare yourself for a Caribbean buffet lunch and an open bar during this unforgivable experience in Sint Maarten.

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.

Enjoy a relaxed half-day sailing and snorkeling experience from Providenciales without the hassle of planning logistics or spending an entire day at sea. Cruise along Grace Bay aboard a catamaran, sipping rum punch as you watch out for dolphins. Anchor at a secluded reef to snorkel using the provided gear, then head ashore to explore pristine beaches and spot native rock iguanas.

We are a boutique catamaran specializing in private trips for families and small groups looking for a special day on vacation, We avoid the crowds of the party boats. A more personal, laid back snorkel & sailing cruise! 200+ five star reviews on google Our tour is customizable so we don’t have to stick to the usual itinerary, we can cater to earlier start times for cruise ship guests. You can meet us at the beach. After boarding our certified guide leads you into the underwater world. Home of tropical fish, rays, corals, shipwrecks and sometimes turtles. We keep it simple, Our local owned 30ft racing style catamaran has high quality snorkeling gear, life jackets, music and light drinks/snacks. After swimming we take a relaxing cruise along the scenic coast line with complimentary authentic rum punch :) We can also offer longer charters with food included or you can Checkout out shared morning charters on our sister page ches surf school

Discover the beauty of the Caribbean on a 4-hour tour to the stunning Icacos Island. This trip offers the perfect blend of relaxation and adventure with two exciting stops: one for snorkeling among vibrant marine life and another to soak up the sun on the beach. Savor a delicious buffet-style lunch served aboard the catamaran, along with refreshing drinks and all necessary snorkeling equipment provided. Ideal for families and groups, this unforgettable experience departs from Fajardo at 9:00 AM and returns at 1:00 PM and the afternoon tour from 2:30pm to 6:30pm - 4-hour tour to Icacos Island with snorkeling and beach time - Buffet-style lunch and refreshing drinks included - All snorkeling equipment provided for your convenience - Perfect for families, friends, or anyone looking to unwind in paradise

If sailing into the sunset while sipping champagne sounds like your idea of a good time, this St. John sailing experience may be just what you need. With this group cruise, you'll sail from the Westin on St. Johns out into the Pillsbury Sound aboard a 55-foot catamaran, where you'll be served champagne, as the sun sets into the sea.

Skip the standard boat tour and enjoy a mimosa brunch experience while sailing across Aruba's waters on this group morning snorkellng 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 clear waters. Well-suited for travelers looking to take a break from land and unwind out at sea.

Set sail on St Thomas' aquamarine waters during this 3-hour sailing excursion from Frenchman's Cove. Step aboard the 54-foot (16-meter) catamaran and meet your friendly captain and crew. Head for the serene waters of Little Buck Island National Wildlife Refuge, where you'll don the provided snorkeling gear and jump in to snorkel among the vibrant marine life. Snacks, pirate tattoos and unlimited drinks from the open bar are included.

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.

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.

Catch the sunset and feel the salt-kissed breeze from Aruba's crystal waters on this evening cruise. Hop aboard a custom built comfortable open-deck catamaran and set sail, taking in views of the coastline and sights such as Eagle Beach, Palm Beach, and the California Lighthouse. Along the way, sip a cocktail, sway to the rhythm of island tunes, and enjoy snacks as you view the setting sun.

Combine sailing and sunset in one excursion—and enjoy views of St. Thomas you can’t get on land—on this day’s end sunset cruise. Board your catamaran at The Westin St. Thomas Beach Resort & Spa and set sail along the coast. Sip on included alcoholic beverages while soaking up the views and the sunset.

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.

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.

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.

Snorkel at the famous Antilla shipwreck during this happy hour sail on a luxurious catamaran. On this sailing excursion, meet the ship's friendly crew and enjoy complimentary snacks and drinks from an open bar. Opt to upgrade your tour to a 'snuba' dive, which combines snorkeling's simplicity with the depth of traditional scuba diving.

To end a perfect day, join this tour aboard a classic schooner in Grand Anse Bay, Grenada, where you’ll sip champagne as the sun sets. This group tour keeps costs down while offering beautiful sunset views, a glass of bubbles, an open bar, and freshly prepared antipasti. Note that a weight limit of 270 pounds applies for safety.