Top Caribbean Sailing Tours

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!

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.

The island of Jost Van Dyke is a beautiful place to spend a day on the sand, but many tours depart later in the morning, which means less time on the island. This catamaran excursion gets you out to sea bright and early, with a stop along the way for swimming and snorkeling.

Sail to Anguilla aboard a catamaran on this full-day cruise from St. Maarten. Stop at Prickly Pear Cay to lounge in the shallows of the small island's pristine beach or snorkel among the tropical fish that inhabit the colorful coral reef. Enjoy a buffet lunch right onboard and an open bar.

Encounter the amazing beauty of Curacao’s West Coast on this sailing adventure. Hope aboard a comfortable catamaran and relax as your crew ferries you to two mostly unvisited beaches. Take the chance to sunbathe, snorkel and swim while the crew provides you with a delicious lunch. With the premium bar opened from around midday, enjoy a variety of beverages as you take in your magnificent surroundings.

Spend the day on your own Luxury Yacht. This price is all inclusive for the Yacht, up to 12 people. You can select a half or full day charter. Visit the islands and harbors of St. Thomas, Buck Island, Water Island, and maybe even a secret cay! S/Y Pisces is a 47′ luxury Leopard Catamaran with a spacious salon that opens on to an expansive back deck with comfortable seating. The bow of the boat offers relaxing seating with bean bag chairs and two large trampolines for group conversations, breezy tanning or turtle watching. Equipped with the latest in audio technology, Pisces has a JBL sound system with Bluetooth capability to ensure you travel with your favorite tunes. There are plenty of water toys to keep you entertained, from snorkeling equipment and relaxing floats to beach games. You and our captain will design an itinerary that best meets your needs. All departure times are listed in Local Island Time.

Experience the thrill of multiple adventures on this epic tour from Punta Cana. Relax aboard a double-decker catamaran, discover wonders of the sea, and enjoy close encounters with marine life. Snorkel in a spectacular barrier reef surrounded by tropical fish. This popular tour option includes unlimited drinks on the best party boat around and is perfect for fun with family and friends. After you get a taste of life underwater, explore it from above with a thrilling parasail above the water!

Sail and snorkel with turtles off west Barbados without the expense and fuss of a private boat charter and with everything provided for you. After boarding a luxury catamaran with a limited number of guests, absorb the breezes, music, and views and arrive at a turtle site before the crowds. Snorkel among the wild turtles and fish before enjoying an on-board open bar and lunch buffet. Snorkel gear and hotel pickup are included for a complete experience.

Experience the U.S. and British Version Islands in style, with this private boat charter. You and your party will hop aboard a 54-foot vessel, where you'll get a chance to customize your tour with your captain. Then it's off to sea, where you'll get the chance to visit white-sand beaches, cruise up to floating taco and pizza restaurants, or stop to snorkel in crystalline waters.

LETS PARTY...!!! STRICTLY OVER 18's From pick up to drop off, enjoy the ONE LOVE vibes Bob Marley sings about When arriving at the departure area of NEGRIL 7 MILE, the party starts, with DJ's playing and fun and games on the beach are just the start of your day, we set sail for the coral reef, where you get to snorkel if you wish, view the beautiful marine life of Negril, after about an hour we sail to Ricks Cafe, watch as the cliff jumpers wow you with their show and skills, with a Dj and band depending on the day, you can party your day away, then after all that we still get to sail back on the sunset, with a rum punch in hand or an ice cold Red Stripe watch as the Sunset on your most amazing day ALL GUESTS - Will also be able to have a little shopping stop included and get 20% off at the store

Cruise around St. Maarten with stops at Tintamarre, Creole Rock, and Grand Case on this full-day sailing excursion. Explore the lovely natural beauty of Tintamarre, then head to Creole Rock for some of the island's best snorkeling. Lunch is then served on board. Cruise down the coast after lunch and sail down pass Marigot, Low Land with a stop at Long Beach for our Floating Bar. Sunset sail back with our festive crew.

See the bioluminescence of glow worms on this sunset cruise from Providenciales in Turks and Caicos. Following the full moon every month, the waters of Caicos Bank experience a unique natural phenomenon when glow worms emit pulses of green light during their spawning cycle, lighting up the shallow waters. Enjoy refreshments, light bites, and hotel pickup from select Grace Bay beach hotels while aboard the cruise.

Enjoy a morning out on the water in Montego Bay. On this private tour you’ll be taken on a cruise around the bay, followed by a snorkeling stop at the Montego Bay Marina using the provided snorkeling gear. Finish off with a delicious lunch of local specialties, such as coconut shrimp. This is a fun half-day trip that’s ideal for couples or families.

Set sail aboard a double-decker catamaran in the Caribbean Sea, beginning with hotel pickup in Punta Cana in the morning or afternoon. Snorkel in crystal clear waters and head to a sandbar with a floating open bar. It's ideal for families and friends. The boat comes complete with an open bar, snacks, fruits, juice and snorkelling gear. Make your Punta Cana Vacation memorable

Set sail from St. Thomas to the island of St. John with this luxury catamaran dinnertime cruise, ideal for those who want to dine at the St. John restaurant of their choosing. You'll enjoy cocktails as you make your way to St. John, with plenty of time on the island for dinner on your own. Cordials will be served on the return journey home.

Enjoy an exciting excursion on a private catamaran that will take you to explore the crystal-clear waters of a tropical paradise. During the trip, you will have the opportunity to immerse yourself in three stops: 1-Snorkel. where you will discover the wonderful marine life that hides beneath the surface. 2-From the comfort of the catamaran, you can spot dolphins playing in their natural environment, these charming marine mammals. 3-To relax even more, we will anchor in a natural pool, an idyllic place where you can swim in shallow waters and enjoy a serene and beautiful environment. While you delight in the views and activities, you will have access to an open bar that offers refreshing drinks, exquisite tropical cocktails and beer throughout the trip. And to complete this unforgettable experience, we will delight you with a delicious Dominican lunch prepared with authentic and fresh flavors that will transport you to the culinary essence of the region.

Grenada's underwater highlights are best reached by boat. Sail out on a full-day cruise to snorkel the Underwater Sculpture Park with a guide, then carry on to Flamingo Bay Reef. Break for a buffet lunch prepared on board, and sip prosecco with appetizers on the sunset sail back to port.

Get a peek at the Dominican Republic's rich marine life without getting wet during this 3-hour snorkeling excursion. See clusters of colorful coral and schools of fish darting under you; opt to use the provided snorkeling gear for a more in-depth look. Learn about the marine flora and fauna from your local guides. Stop at a natural swimming pool for a dip and an opportunity to purchase drinks at the swim-up bar. Back on board the boat, toast your trip with some Mamajuana, the locals' favorite drink. Round-trip transportation from Punta Cana hotels is included.

Parasail 500 feet (150 meters) above the coast of Punta Cana, then go snorkeling off a party boat during this thrilling excursion. Don a safety harness and ascend into the sky, getting panoramic views of the spectacular Dominican coastline. Then, board a catamaran and set sail for a local snorkeling spot, diving in to swim with tropical fish among coral reefs. Sip drinks from the onboard open bar and stop at a natural swimming pool for a relaxing dip in the warm water. All equipment, snacks, drinks, and round-trip transportation from Punta Cana are included.

Admire Aruba at its most magical on a sunset cruise that captures the spirit of Havana, Cuba. Sip Cuban cocktails, dance to Latin beats, and sample snacks from the Caribbean island as you escape the crowds on land and admire Aruba’s coastline from the water. Plus, an onboard salsa teacher helps you supercharge your dancing skills.

Spend a different time aboard this boat animated by a staff that will make you enjoy a pleasant time. A great way to spend a day on the coast of Punta Cana, this party boat cruise offers a mix of fun activities. The first activity you can enjoy is snorkeling where you can observe a wide variety of tropical fish and travel to a natural ocean pool. (You will have a brief stop where you can see dolphins from afar) • Enjoy music, dancing and a festive atmosphere all the way back to the dock. • Half-day cruise on a party boat or Catamaran • Get out on the water: slides and snorkeling equipment are provided. • It is not necessary to pay for drinks as the boat has an open bar. LIVE AN UNFORGETTABLE EXPERIENCE! It is recommended for private parties, birthdays, weddings or for any type of event. If your group is more than 30 people you can request the private boat without any additional cost.

Sail between St. Kitts and Nevis aboard 65-foot catamaran Swaliga in a relaxed, spacious setting capped at 40 guests for comfort. This is not a crowded party boat - there is room to move, unwind, and enjoy open-deck views. Our route along the South East Peninsula offers typically calm Caribbean waters, snorkeling in clear reef sites, and beach time on Nevis - all timed for a smooth, stress-free return to port. Professional crew manage safety, service, and pacing so you can fully enjoy your day on the water.

Enjoy the world of waterspouts with this Punta Cana party cruise that includes snorkeling and hooka diving. Discover the sea and sky alongside your fellow travelers and enjoy life lived to the fullest in a tropical paradise.

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