Top Caribbean Sailing Tours

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.

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.

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 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.

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.

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.

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.

Board a classic West Indian sloop for a relaxing sail around Little Bay. Complimentary use of the boat’s snorkeling gear and swim aids is included. Slip into the sea alongside tropical fish, sea turtles, and water birds and then enjoy a variety of alcoholic and nonalcoholic beverages."

(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.

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.

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.

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.

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.

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.

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.

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.

Set sail aboard a catamaran and explore the Turks and Caicos Barrier Reef on this 4.5-hour half-day excursion departing at 10:30AM. 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.

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.

Discover Aruba's Beauty Embark on the Tropical Sailing Experience from Varadero Marina Aruba, with morning and afternoon sails available. Cruise past the picturesque Spanish Lagoon, and the Aruba Desalination Plant. Indulge in a delightful lunch or early dinner at Mangel Halto Reef, where thrilling snorkeling awaits. Relish the beauty of a captivating sunset.

*Professional and friendly crew* *Snorkeling equipment and safety briefing* *Delicious snacks and refreshments* *Access to the rope swing and diving platform* *Comfortable seating and shaded areas* Embark on an unforgettable adventure aboard our luxury catamaran! Experience the stunning beauty of the coastline, crystal-clear waters, and vibrant marine life on this exclusive catamaran cruise. Perfect for families, couples, and groups looking for a mix of relaxation and adventure.

Experience an unforgettable day of fun in the sun on our party catamaran and snorkeling tour in Montego Bay! Swim and snorkel in the crystal-clear waters of the Caribbean Sea, discovering vibrant coral reefs and colorful marine life. But the excitement doesn't stop there - our catamaran is equipped with a top-of-the-line sound system, a fully stocked bar, and a lively crew ready to keep the party going. Dance to the beat of the music, sip on delicious cocktails, and soak up the stunning views of the Jamaican coastline. This is not your average snorkeling tour - it's a one-of-a-kind experience that you won't want to miss. Book now for the adventure of a lifetime!

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.

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.