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.

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.

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 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. Hotel pickup is included for added convenience.

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.

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.

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.

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.

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.

Explore the waters around Aruba aboard a 65-foot (20-meter) catamaran, the 'Arusun'. 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.

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.

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.

Skip the standard boat tour and enjoy a sail across the turquoise waters of Aruba on this unique morning snorkeling cruise that includes a light brunch, lunch, and an open bar. Set sail aboard a custom-built catamaran and drop anchor at three diving stops to explore marine life and shipwrecks in the crystal-clear waters. Be charmed by Caribbean music and sea breezes as you sip your drink while lounging on the boat—it's perfection in paradise.

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.

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.

(Small group) We are the only catamaran that sails early to avoid the crowds of commercial tours. That’s our niche! Che’s snorkel focused trip has a laid back, personal feel. customized to suit you with only 10 guests. #1 snorkel tour, Check out our reviews! The coral reef is home to the famous sea turtles, tropical fish, rays and shipwrecks! The certified pirate crew will safely guide you into the underwater world before enjoying a scenic sail along the luxurious west coast. We offer eco friendly 3h cruises at the best price. Our local owned boat has premium snorkeling gear, life jackets, relaxing music, complimentary snacks & authentic rum punch :) Free transportation included from most hotels & air bnb in our pickup zone, or you can meet us at the beach. Free bonus underwater photos if conditions allow *read full information details *If our trip is fully sold out please WhatsApp us, we can reopen unconfirmed slots.

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.

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.

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!

Discover the pinnacle of luxury aboard Barbados’ newest gem — our 30ft double-decker pontoon boat. Designed for intimate gatherings of up to 15 guests, this exclusive experience combines modern comfort with first-class hospitality. Our exceptional crew, gourmet cuisine, and personalized service set us apart, ensuring every moment on board is as memorable as it is indulgent. Whether you're marking a milestone or simply savoring the beauty of the Caribbean, we specialize in creating unforgettable celebrations — from birthdays to anniversaries — in an extraordinary setting.

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.

Spend a day sailing around Saint Maarten aboard a trimaran and immerse yourself in the beauty of the Caribbean. Sail along the island's south coast and up the Anguilla Channel, stopping at a bay to snorkel and swim in the pristine waters. Enjoy the beautiful scenery as you sail by and feast on lunch, snacks, and drinks on board.