Top Caribbean Sailing Tours

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.

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.

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.

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.

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.

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 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.

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.

Spend a day on the water with Reve de Nav's charter to Les Saintes from Basse-Terre. Enjoy sailing to various points of interest in Guadeloupe like Cabrit Island and Terre-de-Haut before pausing to swim or snorkel. It takes two hours to sail to Les Saintes so you'll even have the chance to helm the ship alongside your captain-teacher. A Creole meal is served at lunchtime. Arrive back at Riviere-Sens Marina at sunset.

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.

(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. 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.

Set sail on the crystal blue waters surrounding Punta Cana on this small-group experience that's limited to just 16 guests. Swim in a nature reserve, snorkel in the seas and enjoy drinks aboard your comfortable catamaran. Relax in one of the boat's hammocks and let the crew paper you with strong tropical cocktails. Anchor in a sandbar and enjoy beverages from a floating bar as part of this wonderful water experience.

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.

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.

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.

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.

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.

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.

Navigate the seas aboard an authentic sailboat during this excursion in the Bay of San Juan. While most boats these days have noisy motors, this sailboat experience exclusively uses the power of the wind. 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.

Step aboard the Flying Frenchman, our newly designed, state-of-the-art, luxury sailing catamaran for a fun and relaxing sunset sail departing from Frenchman’s Reef. Take in a magnificent Caribbean sunset while under sail and enjoying a chef's selection of hors d’oeuvres and open bar. This luxurious sunset sail is perfect for couples and families alike.

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.