Top Caribbean Sailing Tours

Experience the stunning southern coast of Puerto Rico on this full-day, private boat tour. Climb aboard your sailboat with your group and venture out to explore the Jobos Bay Reserve, Cayo Caribe, and other wetland locations. Use the provided snorkel equipment and listen to informative commentary from your captain about local marine life.

We are a family owned small business; we have a love for true sailing and authentic relationships here in the islands. Looking for more time on the water? Join us for our all inclusive private day sail adventure as well!

Spend the day aboard a 40-foot sailboat with this St John day trip, departing from Cruz Bay. You'll visit a quiet cay for snorkeling and swimming before making your way to a second area for more swimming plus white-sand beach time and an included lunch before returning to Cruz Bay.

Get up close to Antigua’s vibrant marine life on this private snorkeling tour. Climb aboard a catamaran and set off into the sea. Snorkel, swim or relax on deck as you take a break from the island crowds. All this will build up an appetite, so enjoy a stop off at a local restaurant for lunch. Perfect for a group or family looking for something to do that will keep everyone entertained and happy.

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.

Skip the humdrum boat tour and instead set off on an action-packed pirate cruise aboard an 85-foot (26-meter) teak schooner. Enjoy a half-day cruise to multiple sites for swimming and snorkeling with tropical fish, plus see a shipwreck from World War II. A barbecue lunch, open bar, snorkeling gear, and a rope swing on the boat are provided for your enjoyment.

This boat is one of a kind, specially designed for underwater research and once part of Jacques Cousteau's legendary fleet. It features an air-conditioned underwater observation deck, providing comfort while you explore the marine world. It’s not just a tour; it’s an extraordinary opportunity to step into a piece of maritime history and experience the ocean as Cousteau himself might have.

Learn to sail across the azure waters of the Caribbean Sea with this private sailing lesson in St. John. Board your vessel with your group and “captain” your boat for the whole day, or relax on the decks. Your day includes swim and snorkel stops, deli sandwiches, snacks, mixed drinks, beer, soda, juice, and water.

Grab up to five of your travel companions for a private day of snorkeling and sailing from Sapphire Beach Marina. Your captain will take you to top snorkeling spots around the Virgin Islands, with an included grilled lunch served between stops and an open bar on board. This private experience offers plenty of opportunities to customize the day to suit your interests.

Cruise along Punta Cana's coastline aboard your own private catamaran during a personalized excursion for up to 30 people, ideal for celebrating a special occasion or for those who want to experience multiple island highlights in a single trip. Swim with sharks and stingrays or snorkel around the barrier reef and to secluded beaches, and customize your itinerary according to personal preference. Your charter includes on-board entertainment and an open bar.

Charter a private sailboat for a day of cruising and snorkeling in the Virgin Islands. You and your group of up to six people will have the entire boat to yourself, making it easy to customize your experience. You'll have plenty of time to snorkel, swim, and visit beautiful beaches, and lunch will be prepared for you right on the boat.

Prepare for the adventure of a lifetime aboard a state-of-the-art, custom-built catamaran! Set sail across the crystal-clear Caribbean as you journey to one of Nassau’s most stunning coral reefs. There, you’ll dive into an unforgettable underwater experience, snorkeling for approximately one hour among vibrant fish, colorful corals, and an incredible array of exotic marine life. It’s visual paradise as you glide above Nassau’s shimmering, jewel-toned seas. Your catamaran offers exceptional comfort with spacious decks, cushioned seating, and private bathrooms—plenty of room to stretch out, relax, or socialize with fellow guests. On the return voyage, bask in the warm Bahamian sunshine while enjoying complimentary drinks from our onboard bar.

Book this private tour for adults, which includes ziplining, horseback riding, and an ATV safari all in one experience. You’ll begin the experience with hotel pickup to keep things easy, then your adventures begin. Have thills on the zipline, ride your horse in the sea, and snorkel in the clear waters, too.

Benefit from personalized attention and a flexible tour during this day-long cruise from La Romana. Choose your own itinerary and let the crew show you hidden gems and off-the-beaten-path spots that you wouldn't find on your own. Stops typically include Catuano, Saona, and Las Palmillas; you'll learn about Dominican culture, history, and nature through guided commentary as you travel.

Benefit from personalized attention and a flexible itinerary on this private sunset sail of Grace Bay from Providenciales. Just walk down to your resort's beach for water pickup, step aboard the catamaran, and sit back to enjoy epic sunset views. Munch on appetizers such as cracked conch and sip beer, wine, and rum punch. Toast to your vacation and your friends and loved ones as the sun sinks below the horizon, then return to your resort for drop-off in plenty of time for dinner.

Combine a tour to Saona Island and an all-terrain vehicle adventure in a single package, saving you from sorting out the logistics yourself. Embark on full-day tour via boat to the idyllic Saona Island, which includes a barbecue lunch and a stop at the natural pool. The ATV tour takes a half-day, where you and a guide will make your way through the rugged parts of the island to see the "real" Dominican Republic's countryside.

Spend a day immersed in the beauty of the Caribbean on this full-day excursion to Saona Island from Punta Cana. Climb aboard a catamaran and party on the way to Saona. Then, enjoy plenty of time to swim and sunbathe before tucking into a delicious buffet lunch on the beach. On the way back, stop in Palmilla to swim in the natural pool.

Explore the turquoise waters of Sint Maarten with this tour. Over a full day, you'll experience all that the island has to offer. Everything from cruising on the water, seeing the sights, snorkeling, and proper sailing. Sophisticated meals are served across the day - Gouda Cheese, fresh baguette and barbecue lunch will leave everyone satisfied. Everything is flexible and can be personalized to your preferences.

Grab a group of friends for a fun private boat tour at Punta Cana. The three-hour itinerary can be customized to suit your needs, but you can enjoy a combination of swimming and snorkeling in the warm sea, relaxing on deck while enjoying the views, and chilling out with a cold drink. This is a great way to see the sights while spending quality time with your family or friends.

Take a private sunset cruise aboard a 40-foot-long sailboat with this experience. You and your group of up to six people will have around two hours on board, where you'll take in sunset views while you feast on hors d'oeuvres and sip on cocktails, all included in the price of the tour.

Catch the most amazing sunsets from a secluded spot on the Jobos Bay National Estuarine Research Reserve (JBNERR) with our experienced USCG Captain and crew, in the comfort and privacy of our 36-foot sailboat fit for six (6) passengers. Your departure time is schedule and confirmed according to the sunset hours. Private Day Sail Charters depart from the gorgeous town of Guayama at the docks of the Guayama Fishing Club, famous for its stunning sunset views. The departure dock in the town of Guayama is about an hour drive away from San Juan, through the amazing landscapes of the Cordillera Central, the main mountain range in Puerto Rico.

With this private catamaran tour, you'll enjoy a customized navigation within the accepted areas, play your own music, and have privacy to enjoy time with your loved ones. Your lunch will be a seafood feast, freshly prepared and grilled on board. You'll also have the chance to snorkel at the Cabeza de Toro reef and relax in the natural pools. Because this is a private tour, you can specify any special event you're celebrating so we can add a personal touch to your boat at no extra cost.

Our team knows how to blend adventure and relaxation perfectly. From snorkeling with sea turtles and exploring shipwrecks to sipping rum punch as you sail across Carlisle Bay, we create an authentic, personal, and unforgettable experience in a small-group setting. To top it off, you can choose to stay and enjoy Carlisle Bay’s famous soft white-sand beach after your cruise.

Start another day in paradise with cool Caribbean breezes and reggae tunes on a private catamaran cruise from Negril. Stretch out on the spacious vessel and sip unlimited drinks from an open bar as your captain navigates to swimming caves or prime snorkeling spots along Jamaica’s western coast. The charter requires a minimum of 21 guests, making it ideal for large groups celebrating weddings, birthdays, and other special events.