Top Caribbean Sailing Tours - page 2

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.

Watch the sunset and dine on Creole fare aboard a catamaran during this excursion from St. Maarten. Sip drinks from the open bar and munch on complimentary appetizers while the sun sinks below the horizon. Once twilight falls, enjoy a buffet-style Creole dinner, followed by dessert and Caribbean rum. Hit the dance floor to island beats while the boat sails back to the marina.

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.

Explore Aruba’s coast on this morning sailing trip. Board a catamaran limited to fewer than 35 guests and unwind as the captain and crew take you to Boca Catalina Beach. Enjoy snorkeling, swimming, and paddling, or simply soak up the sun. All these activities build up an appetite, so enjoy snacks, drinks, and a BBQ lunch onboard. Perfect for anyone looking to escape the mainland for a short while.

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.

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.

Head out for a day of snorkeling with this all-inclusive yacht trip. You'll visit two different snorkel spots, USVI St. John National park and nearby coral reefs, and snorkel equipment will be provided. As this is an all-inclusive tour, you won’t need to worry about packing your meals—breakfast and lunch will be served plus free soft drinks and alcohol will be available on board.

Set sail across the Caribbean on this 1.5-hour cruise from San Juan and enjoy unforgettable views of the Puerto Rican capital. Hop aboard a traditional sailboat and sip complimentary drinks as you cruise along the coast. Keep your camera to hand as you pass landmarks and spot dolphins and sea turtles swimming and playing around the boat.

Climb aboard the catamaran "The Phoenix" for a sail around the sights of Sint Maarten. Explore the warm Caribbean Sea with ease with the supplied water gear, for a day of swimming, snorkeling, paddle boards, or relaxing. Indulge in fresh fruit, pound cake, and a freshly prepared lunch alongside refreshing cocktails, beer, and non-alcoholic beverages. Finish the day watching the planes take off as you sail past Maho Beach—a must-do when visiting the island (weather permitting).

The discerning visitors choice for over 20 years. The one excursion company that is all about you. This excursion is a genuine sailing adventure, we actually sail. Help us hoist the sails or just sit back, relax and experience the magic aboard our 48' custom day charter catamaran. Our friendly, native Captain and professional crew, will attend to your every need while sailing along the coastline of Grace Bay and the outer Cays. Watch for Dolphins, Rays and Turtles from our bow nets as you soak up the sun and enjoy your music or ours, domestic and imported beers, rum punch, fresh fruit, chips & dip and an open bar. Anchor at the Captain's favorite spot, swim and snorkel amazing coral reefs teeming with fish, and boasting a maze of tunnels, caverns and beautiful coral formations. Explore breathtaking deserted beaches with sugar fine soft sand, naturally carved limestone cliffs and outcroppings. We can also customize the trip to your liking. Sail, Swim, Snorkel, Relax, Explore, Learn.

To end a perfect day, join this tour aboard a classic schooner in Grand Anse Bay, Grenada, where you’ll sip champagne as the sun sets. This group tour keeps costs down while offering beautiful sunset views, a glass of bubbles, an open bar, and freshly prepared antipasti. Note that a weight limit of 270 pounds applies for safety.

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.

Experience the best of two tropical islands! Sail to the island escape of St. John from St. Thomas aboard the beautiful Flying Frenchman. After snorkeling in crystal blue waters, enjoy lite bites and a full bar. Explore St. John on foot and return to enjoy the full bar on your return sail back to St. Thomas.

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.

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.

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!

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!

Spend the day sailing around the Virgin Islands on this all-inclusive charter, with departures from Red Hook. With group size capped at six, you’ll have plenty of space onboard to relax and enjoy the views. Enjoy snorkeling with the provided equipment, with a guide to lead the way, and instruction if needed. A Mediterranean lunch is provided onboard, along with a fully stocked bar.

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in small groups of up to 10, ensuring a personalized and high-quality experience for all. The bay boasts a vibrant array of marine life and magnificent Green Sea Turtles. Guests often spot blue tangs, sergeant majors, fairy basslets, yellow snappers, and more! Occasionally, you might encounter rare creatures like squids, seahorses, rays, and manatees. We suggest the morning time slots as the marine life is more active. Receive a complimentary video to commemorate your unforgettable adventure. This Activity is suitable for ages 8 years and above.

Get access to the National Wildlife Marine Refuge on a sailing yacht during this half-day tour from Charlotte Amalie. Learn about the turtles' behavior and habits through guided commentary and watch them munch on sea grass before sailing out to Buck Island, where you can swim and snorkel to explore the underwater world. This convenient tour combines two of the most popular water activities in a single booking.

Go sailing and watch the sunset on a cruise from San Juan. Get great photo ops of Puerto Rico’s coastline and enjoy a comfortable sail on the Caribbean Sea. Your captain shares commentary about the region and provides complimentary drinks for your group of no more than six people.

Explore Aruba’s coastline on this sailboat experience. Including stops at beaches and a shipwreck, guests are welcome to snorkel, swim, paddleboard, or simply soak up the atmosphere. All this activity will build up an appetite, so enjoy an onboard BBQ meal and sip on included alcoholic drinks. Finish off your trip by catching the sunset, all from a unique sea perspective. Hotel pickup is included for added convenience.

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.

Sail the calm, azure waters of San Juan Bay at sunset during a cocktail cruise. Enjoy a warm welcome aboard from your friendly captain and crew, then settle in for a scenic ride. Watch the island coastline glide by as the sun sinks toward the horizon. Sip a complimentary rum punch or sparkling wine with your family and friends and listen as your captain points out landmarks like El Morro Fort and San Juan Gate. Arrive back at the dock in time to continue your evening in San Juan.