Top Caribbean Sailing Tours

Sail and snorkel around Cades Reef and the surrounding beaches during this 6-hour boat tour from St. John's. Relax on the white sand while the crew serve you drinks and prepare a barbecue lunch. Round-trip transportation from St. John's hotels or the cruise port included.

Spend the day on your own 50' Luxury Catamaran Yacht. This price is all inclusive for the Yacht, up to 12 guests. You can select a half or full day charter. Visit the islands of St. Thomas, St. John and surrounding cays. SY Sirena is a 50′ Luxury catamaran with a spacious salon that opens on to an expansive back deck with seating and dining. The bow of the boat offers relaxing seating with bean bag chairs and large trampolines for group conversations, tanning or intense turtle, dolphin watching. There are plenty of water toys to keep you entertained, from snorkeling equipment to relaxing floats. Price includes ice, soda, beer and rum punch. You and our captain will design an itinerary that best meets the needs of your group. *Please note the BVI is not available on this vessel, but a visit to the BVI can be booked under Product Codes 111649P24 or 111649P25. Departure from American Yacht Harbor in Red Hook; pickup from Cruz Bay, STJ possible with advance request after booking.

Take in stunning views of the Caribbean with this luxurious half-day cruise in Barbados. You won't have to worry about a drink tab—an open bar comes with your package. Relax aboard a double-decker pontoon boat for unobstructed views of the water. Unlike more crowded options, this cruise offers a small-group setting.

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.

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.

Spend a day sailing and snorkeling with just five other passengers with this full-day sailing and snorkeling experience. You’ll set sail in the morning and head out to some of the USVI's prettiest spots for swimming and snorkeling, with a stop for lunch along the way. While locations may vary, the crew will do their best to ensure you beat the big cruise ship crowds.

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.

Spend a memorable sunset sailing into the waters around St. John on this cruise from the Ritz-Carlton in St. Thomas. You’ll be treated with refreshing beverages while you sail, with plenty of time to take photos or just enjoy nature’s light show as the sun sets below the Caribbean horizon.

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 views of Aruba you can’t get on land during this morning or afternoon cruise. Unlike on big party boats, the vessel accommodates a small group, so everyone can spread out and enjoy some peace and quiet. Use the provided snorkeling gear to explore the underwater world, then refuel with a tasty lunch or dinner, with various options. Afternoon cruises can watch the sunset, too.

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.

Sail into the sunset on your own private cruise by booking this excursion on the Frances Anne for private groups of up to six people. You’ll have the option to jump into the water for a bit of swimming and snorkeling, though you may want to stay on board, where a charcuterie board and alcohol and soft drinks will be served.

Explore St. Maarten’s natural landscape away from the crowded beaches on a boat cruise that departs from Bobby’s Marina. To ensure your comfort and a personal experience, the boat crew provide a buffet lunch, open bar, and snorkeling gear. Stops on the itinerary range from top landmarks to secluded snorkeling locations often missed by visitors.

Enjoy an afternoon of fun in the sun and sea, topped off with a barbecue of grilled seafood. Sail on a comfortable catamaran around the sparkling coastline of Bonaire and Klein Bonaire islands, stopping at the Bonaire Marine Park to snorkel with a guide. Sail to another pretty spot for more water play while your crew prepares your tasty feast on board. Return to port as the sun is setting on a glorious day.

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.

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

Swim with green and hawksbill sea turtles on a sailing adventure from St. Thomas to Maho Bay, St. John, and Honeymoon Beach, St. Thomas. You'll make two snorkeling stops on your voyage, with a picnic lunch served on board in between. After swimming, enjoy free alcoholic beverages from the on-board bar. Note that onsite parking at the Ritz-Carlton now costs $30. Bring your own towel to help conserve the island's fresh water.

Navigate the seas aboard an authentic sailboat during this 1.5-hour excursion in the Bay of San Juan. This sailboat experience uses only wind power, avoiding noisy motors and crowds. 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.

Embark on a catamaran cruise on the turquoise waters off Punta Cana with other families for a fun day on the water. Everything is taken care of for you: use of snorkeling equipment for both kids and adults, as well as lunch (kids menu available) on board the boat and convenient round-trip transportation from your hotel.

Enjoy a day out of the water of St. Thomas on this small-group sailing excursion. Spend the morning sailing through the protected waters of the Virgin Islands National Park. Enjoy pristine beaches and look for turtles, sting rays, and tropical fish while snorkeling. Afterwards, visit Caneel Bay, which is only accessible by water. After an onboard lunch, enjoy time at Honeymoon Beach.

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

Explore the Caribbean waters around Puerto Rico on a sailing tour from Fajardo. Join a small group and head to the nature reserve on Piñeros Island to discover the local biodiversity. Your captain makes several stops throughout the day and you can choose to swim in the pristine waters, snorkel in the abundant reefs, or simply sunbathe on the white-sand beaches. A delicious lunch and drinks are included.

Discover the underwater wonderlands of Cap Cana during an excursion that combines swimming, sailing, and snorkeling in the warm waters of the Caribbean Sea. You'll discover nature-rich spots that are only accessible by boat and increase your chances of spotting of tropical marine life. Plus, unlimited access to an open bar plus a seafood dinner at a floating kitchen are included.

Imagine a blissful snorkel stop in the crystal-clear waters in Turks & Caicos aboard a luxury catamaran. As the catamaran gently glides over the turquoise waters, you're surrounded by the breathtaking beauty of the Caribbean. The boat is spacious and equipped with comfortable seating, perfect for lounging in the sun or taking in the panoramic views of the coastline. The crew anchors in a prime snorkeling location, where the water is calm and inviting, with vibrant coral reefs just beneath the surface. The boat offers all the premium snorkeling gear you need, from masks to fins, allowing you to effortlessly slip into the water and explore a vibrant underwater world. Schools of tropical fish swim around you, while rays and sea turtles occasionally appear in the distance, making it a magical experience. After snorkeling, relax with a refreshing drink from the open bar. Enjoy a tropical cocktail, ice-cold beer, or a refreshing mocktail.. the bar has something for everyone!