Top Caribbean Sailing Tours

This boat is one of a kind, specially designed for underwater research and once part of Jacques Cousteau's legendary fleet. It features an air-conditioned underwater observation deck, providing comfort while you explore the marine world. It’s not just a tour; it’s an extraordinary opportunity to step into a piece of maritime history and experience the ocean as Cousteau himself might have.

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.

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.

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.

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.

Take to Bermuda’s tropical waters on this boat trip starting from Island Tour Centre, Dockyard. Go swimming, snorkelling, or paddle boarding, or soak up the sun on the boat deck. Don’t worry about hiring any water equipment separately; simply pick up one of the onboard snorkels and boards. Perfect for larger groups and families where some want to relax and others want to have fun playing in the sea.

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.

Finding a quiet place to swim and snorkel around Bermuda can be difficult without a boat. This catamaran cruise takes you sailing around the island before anchoring in a private cove where you can enjoy the water without the crowds. Along the way, your captain shares stories of Bermuda’s history and local legends to keep you entertained.

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.

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.

Enjoy sailing, snorkeling, and shopping all in on tour, without the hassle of booking different activities, on this day cruise from St. Thomas to St. John. Board your catamaran at Frenchman’s Reef and set sail for Cruz Bay on St. John. Browse the shops and enjoy lunch (own expense), and set sail for Honeymoon Beach for snorkeling. On the sail back, enjoy an open bar.

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.

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.

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).

Enjoy both comfort and style as you take in scenic views of Bermuda's coastline on this sunset cruise. Watch the sunset over the water—from a vantage point many travelers miss out on—and relax with a complimentary rum cocktail. As you cruise the pristine waters, listen to entertaining, discussion-style commentary and island music. Feel the warmth of true Bermudian hospitality throughout.

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!

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.

Spend about 6.5 hours sailing, snorkeling, eating, and drinking with this cruise from St. John. You'll start with an on-board continental breakfast, followed by a snorkel stop at a coral reef. Then it's off to a floating taco bar, Lime Out, for lunch, followed by a full open bar on the catamaran after snorkeling and more snorkeling before you head home. Weather conditions determine if sailing is an option.

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.

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.

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.

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

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.