Top Caribbean Sailing Tours

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.

Punta Cana Cruise Experience Snorkeling • Sandbar • Music • Drinks • Pure Caribbean Fun • Open bar • Snacks Get ready to experience the ultimate cruise in Punta Cana!
Perfect for birthdays, bachelor/bachelorette parties, after-wedding celebrations, or a fun day at sea, this exclusive boat rental combines luxury, adventure, & nonstop vibes for an unforgettable Caribbean experience. Party Atmosphere
High-quality party speakers Personalized music (R andB, Hip Hop Reggaeton and more – or bring your own playlist!) AQUATIC ADVENTURES and STOPS Stop 1 – Snorkeling Adventure
Dive into vibrant coral reefs and explore the underwater world Stop 2 – Dolphin Island Cruise
Scenic cruise where you may spot dolphins from the boat Stop 3 – Crystal-Clear Waters
Relax, swim, enjoy tropical vibes and use the onboard water slide - Famous Sandbar Experience
Swim, float, dance, and enjoy Caribbean-blue shallow waters TOUR DURATION 3 Hours Yacht Cruise + 1 hour of transportation services

Climb aboard a catamaran at New Providence Island bound for a day at sea, with all logistics taken care of by someone else. Enjoy the sun and sea breeze, use snorkel gear at Pearl Island, and swim with the Bahamas’ famous pigs. Arrive on Rose Island for a beach party with plenty of drinks and snacks before returning to New Providence Island.

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.

Float past hundreds of years of history and picturesque scenery during this 2-hour sunset sailing excursion in Old San Juan Harbor. Climb aboard the "Amazing Grace," a topsail schooner fashioned in the style of 19th-century American sailing vessels, for an unforgettable ride past the wonders of this historic area. As you sail you’ll enjoy up-close views of Old San Juan sights like El Morro fortress, La Fortaleza, Paseo la Princesa and more, all set aglow by the fading late afternoon light. A guide and complimentary beverages and snacks are all covered.

Treat yourself to a dinnertime sailing trip aboard the luxury 65-foot catamaran Lady Lynsey II. Sail from the Ritz-Carlton to the Lovango Resort and Beach Club on a private island, with cocktails served along the way. At the club, enjoy coastal cuisine by chef Stephen Belie, including a full raw bar and craft cocktails (meal not included). Cordials are served on the return cruise home.

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea ending in an amazing sunset setting. Great for engagements, and any special private event. Come experience the 1st class service by our professional and friendly crew. Our great reviews have positioned us as the #5 Tripadvisor company in Fajardo.

Sail from St. Thomas to St. John on this small-group sailing adventure. Snorkel in the warm waters of Christmas Cove, and enjoy cheese or pepperoni pizza from the floating pizzeria, Pizza Pi. Then sail to Maho Bay, where you can hop back in the water to swim among sea turtles and sting rays.

Set sail aboard your own private yacht on this personalized sailing adventure from Montego Bay, a great choice for families or groups celebrating a special occasion. Opt to snorkel around a coral reef and see tropical fish and maybe sea turtles and starfish; try your luck at deep sea fishing; or simply relax on the yacht's deck and enjoy views of the island. A minimum of four guests is required for this private charter.

Put a new knot on your skill belt with a basic sailing lesson and half-day tour of St Lucia's Rodney Bay. Set out aboard a 40-feet-long racing yacht with an attentive crew who will teach you to fly the jib and hoist the main sail, then allow you to practice on your own. Participate as much or as little as you like: simply sit back and watch the action or go all in and take over the ship's wheel. This spectacular coastline excursion includes both morning and afternoon departures.

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.

Spend your morning or afternoon simply sailing around the Virgin Islands with this private charter on a 40-foot pilothouse mariner. Enjoy easy boarding access at the dock and spend your entire time sailing, though a snorkel stop can be included if requested. Charter includes onboard snacks, alcoholic beverages, soda, and bottled water.

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.

Swap the crowds on land for the tropical beauty of the Caribbean Sea on a private sailing tour of St. Martin on a trimaran boat. Relish the freedom to customize your agenda as you sail to off-the-beaten-path snorkel and swimming spots, and get a new perspective of St. Martin’s coastline from onboard your private vessel.

Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choice between a 37 foot sailboat ot a a high performance Powerboat. Enjoy complimentary local drinks. Your personal tour guide and Pro USCG certified Captain will guide you to stunning and interesting historical points of interest full of Caribbean flare in style and with a high quality sound system. Choose between a bay or sunset water tour. For a minimum of 4 guests or pay for 4 and a maximum of 6. Welcome aboard!

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.

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.

Set off from Saint-Martin for a full day on a wind-powered boat, without an engine. With the captain's help, take the helm and help hoist the sails before stopping to swim and snorkel with the provided equipment. Pirate-themed games and a treasure hunt liven up the day between swims, while observing turtles—and for the lucky ones, dolphins—adds a bit of wildlife to the adventure. The shared trip is limited to seven travelers, which allows time to be spent on changing between navigation, swimming, snorkeling, and games on board, with lunch served during the day.

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.

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.

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.

Punta Cana Booze Cruise Experience Snorkeling • Sandbar • Music • Drinks • Pure Caribbean Fun Get ready to experience the ultimate cruise in Punta Cana!
Perfect for birthdays, bachelor/bachelorette parties, after-wedding celebrations, or a fun day at sea, this exclusive boat rental combines luxury, adventure, & nonstop vibes for an unforgettable Caribbean experience. Party Atmosphere
High-quality party speakers Personalized music (R andB, Hip Hop Reggaeton and more – or bring your own playlist!) AQUATIC ADVENTURES and STOPS Stop 1 – Snorkeling Adventure
Dive into vibrant coral reefs and explore the underwater world Stop 2 – Dolphin Island Cruise
Scenic cruise where you may spot dolphins from the boat Stop 3 – Crystal-Clear Waters
Relax, swim, enjoy tropical vibes and use the onboard water slide - Famous Sandbar Experience
Swim, float, dance, and enjoy Caribbean-blue shallow waters TOUR DURATION 3 Hours Yacht Cruise + 1 hour of transportation services

ARE YOUR READY TO PARTY... this is Strictly and adults only cruise, From the moment you're picked up from the hotel your tour of Jamaica begins, as we set of for Negril, you will get to do a little shopping, before heading to the famous 7-mile beach then its off to snorkel on the Coral Reef where marine life come and take a little look at their visitors, after that we set sail to the Famous RICKS CAFE to watch the cliff jumping and maybe have a dance or two while listening to the DJ do his thing, with pure Reggae vibes we welcome you to Jam Rock.. after that we get you back onboard your catamaran and sail back on the sunset while enjoying a chilled Red Stripe or a Rum Punch

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.