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Top Caribbean Sailing Trips

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San Juan Snorkel and Picnic Cruise

Get a taste of island life during this full-day catamaran cruise and snorkeling trip to a nearby nature reserve, where you’ll explore the tropical isle of Icacos. Pretend you’re Jacques Cousteau as you snorkel among the area’s fantastic marine life, then stroll the deserted beaches of a protected island for some shell hunting and sunbathing. Along the way enjoy a buffet lunch, with included rum punch or piña coladas, plus optional hotel pickup and drop-off from select properties in San Juan.
  • Duration: 8 hours 30 minutes
  • Free Cancellation
  • Duration: 8 hours 30 minutes
  • Free Cancellation
From  
$83.00
From  
$83.00
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Anguilla Day Trip from St Maarten Including Lunch

Sail to Anguilla aboard a luxury catamaran on this full-day trip from St Maarten. Stop at Prickly Pear Cay to lounge in the shallows off the small island's the pristine beach or snorkel among the tropical fish that inhabit the colorful coral reef. Visit lively Road Bay Beach for a barbecue lunch at Roy's Bayside Grill, then hit up some of the beach bars before climbing back aboard the two-hulled sailboat for the trip back to your departure point. Round-trip transportation from select hotels on St Maarten is included, depending on day of tour.
  • Duration: 8 hours
  • Free Cancellation
  • Duration: 8 hours
  • Free Cancellation
From  
$120.00
From  
$120.00
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Champagne Sunset Cruise (Adult Only) in Providenciales

Watch the sunset on the deck of a spacious catamaran off Grace Bay while you enjoy a glass of Champagne. This 18-and-over tour, which includes hotel pickup and drop-off, allows you to enjoy a spectacular sunset while rocking gently on the Caribbean waters. Dine on snacks, including fresh conch fritters, provided by a local restaurant while you toast the gorgeous surroundings with wine, Champagne, rum punch, or soft drinks.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$100.80
From  
$100.80
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Small-Group Day Sail in St Maarten

Cruise on the ultramarine waters off St Maarten during this 5-hour yacht excursion from Simpson Bay. Step aboard the family-friendly yacht, the 'Random Wind', to meet your friendly captain and crew as the boat departs the pier. Find a comfortable spot on one of the boat's cushioned seats in the shade or sun and get to know your small group of 22 people or less as you watch the coastline fade into the distance. Journey to both the French and Dutch sides of the island to visit several beaches and relax in the soft sand. Go snorkeling, stand up paddleboarding or try out the Tarzan swing. Eat a homemade lunch and sip drinks from the top shelf bar.
  • Duration: 5 hours
  • Free Cancellation
  • Duration: 5 hours
  • Free Cancellation
From  
$118.99
From  
$118.99
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Private Half Day Catamaran Sail and Snorkel

Benefit from personalized attention and a flexible itinerary on this private, half-day sailing and snorkeling expedition from Grace Bay. Enjoy views of the beach and sister islands around Providenciales, as well as dolphins, rays, and turtles. Sunbathe on the catamaran's deck, sip rum punch, and munch on chips and salsa. Set anchor at the captain's favorite spot to swim and snorkel using the provided equipment. This trip is flexible and customizable for you and your party.
  • Duration: 4 hours
  • Duration: 4 hours
From  
$1,512.00
From  
$1,512.00
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NEW TO VIATOR

Luxury 47' Catamaran - Private Virgin Islands Snorkel, Sail and Beach Adventure!

The definition of luxury sailing is what you’ll find aboard Sailing Yacht Pisces. Avoid overcrowded tours with no personal attention. This is an intimate, semi-private excursion. A total of only 12 guests will enjoy our 47’ Leopard sailing catamaran. Once on board you’ll find meticulous attention to details throughout the catamaran. There are plenty of water toys to keep you entertained throughout the day, from stand up Paddleboards (SUP’s), snorkeling equipment and relaxing floats to beach games. Our swim saddles and floating drink holders will surely be your favorite for great group conversations on the water. Your private group will have many options for the day. Snorkel among tropical fish, vibrant coral and grazing sea turtles at Turtle Cove in the Buck Island National Wildlife Refuge. Then, have a Pain Killer and relax on the white sandy beaches of Honeymoon Bay on Water Island, perhaps one of the most beautiful bays in the Virgin Islands. Two departures a day at 9am or 2pm.
  • Duration: 4 hours 30 minutes
  • Free Cancellation
  • Duration: 4 hours 30 minutes
  • Free Cancellation
From  
$150.00
From  
$150.00
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Old San Juan Harbor Sail

Float past more than 500 years of history and picturesque scenery during this 1.5-hour 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 such as El Morro fortress, La Fortaleza, and Paseo la Princesa. A guide and complimentary beverages and snacks are all covered.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
$59.00
From  
$59.00
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NEW TO VIATOR

Aruba Sunset Sail Experience

Catch the sunset from Aruba's crystal waters on this evening cruise. Hop aboard a comfortable open-deck catamaran and set sail, taking in views of the coastline and sights such as Eagle Beach, Palm Beach, the California Lighthouse, and more. Along the way, sip a cocktail and enjoy snacks as you view the setting sun.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$55.00
From  
$55.00
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NEW TO VIATOR

LUXURY HALF DAY CATAMARAN TOUR (cruise ship tour)

Fabulous luxury half day charter on Our 48 feet Catamaransailing along St maarten shoresnorkeling & fishing gears included 2 paddles on boardfull open bar & Snacks ,appetisers ,tapas included
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$95.00
From  
$95.00
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Curacao Half-Day Snorkel and Luncheon Sail

Sail aboard a catamaran to several of  Curaçao's top snorkeling sites on this 4-hour tour from Willemstad. Snorkeling equipment provided, barbecue lunch and open bar included.
  • Duration: 4 hours 18 minutes
  • Free Cancellation
  • Duration: 4 hours 18 minutes
  • Free Cancellation
From  
$75.00
From  
$75.00
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Nassau Sail and Snorkel Tour

Relax aboard a luxury catamaran during this 3-hour excursion from Nassau. Sail out to a teeming underwater reef to snorkel among the schools of colorful fish and a variety of coral. Anchor at Athol Island or Spruce Cay, then don the provided snorkel equipment and jump in to the calm turquoise water. Seek out the expert captain and crew for snorkeling instruction and guidance. After you've fully explored the underwater world, climb back on the boat for some refreshments, including the local favorite: rum punch. Let the sun and tropical breeze dry you off during the sail back to shore.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$68.00
From  
$68.00
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St Kitts Snorkel Cruise with Lunch

Bask in the warm waters of the pristine Caribbean Sea during this 3.5-hour snorkeling cruise from Saint Kitts, including open bar and lunch. Take a sail upon the turquoise-blue waters near this tropical island, enjoying sublime views of its craggy peaks, beautiful villas and secluded beaches on your way to the southeast peninsula for your snorkel outing. Then hop in for an underwater exploration of the island's diverse marine life. This combination sailing and snorkel cruise also includes round-trip hotel transport and snorkel equipment.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
$102.00
From  
$102.00
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Aruba Palm Pleasure Snorkel Adventure

Set sail on this half-day snorkeling adventure aboard a 70-foot catamaran. Cruise along stunning turquoise blue waters as you lounge on a relaxing sun deck while sipping strong cocktails. A friendly and professional crew will help you prepare to dive below the surface of the sea, where travelers will find the coral-laden Antilla Shipwreck, colorful coral and plenty of tropical fish. This trip includes round-trip hotel transportation and a savory lunch prepared by top chefs aboard your ship, plus an open bar of tropical drinks and beer.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$94.34
From  
$94.34
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The Original Eco Tour - Full day around the Island of Sint Maarten / St Martin

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. Go ashore in Grand Case, the St Maarten's culinary capital, for a gourmet lunch including wine. Cruise down the coast after lunch past Marigot Bay and Sunset Beach while enjoying an open bar. Round-trip transportation from St Maarten hotels is included.
  • Duration: 8 hours
  • Free Cancellation
  • Duration: 8 hours
  • Free Cancellation
From  
$129.00
From  
$129.00
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Caribbean Dinner cruise

Sail around the coast of Aruba taking in pretty ocean views while also enjoying a Caribbean-style dinner buffet. Feel the spirit of the island as a steel-drum player greets you with Caribbean music as you board the luxury catamaran. Accompanying your buffet dinner is an open bar featuring cocktails, wine, beer, and soft drinks.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
$79.80
From  
$79.80
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NEW TO VIATOR

Day Sail without transportation

First, we sail to the paradise Island of Icacos aboard the modern, 51 ft. sailing catamaran, SPREAD EAGLE II!  The brisk 40 to 50-minute sail to the protected anchorage off of this uninhabited Spanish Virgin Island is beautiful. Sparkling beaches and crystal clear snorkeling waters await. We think you deserve the best, don’t you? Over 65% of our guests are repeats or referrals.The reefs are teeming with parrot fish, foureye butterfly fish, sergeant majors, and wrasse. The variety is too long to list, so you should just come see them all for yourself. Ask one of the crew to see the Fish, Coral, and Shell Identifying Charts on board. SPREAD EAGLE II even provides lunch for the fish. With a little patience, you can get the fish to eat bread right out of your hand.
  • Duration: 5 hours 30 minutes
  • Free Cancellation
  • Duration: 5 hours 30 minutes
  • Free Cancellation
From  
$82.16
From  
$82.16
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Discover Afternoon Snorkel Sail with Open Bar and Snacks

Make multiple stops along Aruba's coast during this afternoon sail in Aruba. Step on board the sailboat and enjoy the coastal views of the white sand beaches on the way to snorkeling spots such as the Caribbean's largest shipwreck, Boca Catalina Bay, and Malmok Beach. Relax on board, dive in to snorkel using the included equipment, and sip tropical drinks from the open bar.
  • Duration: 3 hours
  • Duration: 3 hours
From  
$42.00
From  
$42.00
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Lunch and Snorkel Sail in Barbados

Swim with turtles and snorkel over shipwrecks on this half-day cruise in Barbados. Set sail aboard the ‘Jolly Roger’ schooner and enjoy activities such as plank walking, conga dancing and rope swinging; visit Carlisle Bay and Payne’s Bay for swimming and snorkeling opportunities; and tuck into a delicious, barbecue buffet complete with unlimited drinks from the onboard bar.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$87.00
From  
$87.00
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Negril & Ricks Cafe Sunset Catamaran Cruise

This tour combines a catamaran cruise, snorkeling excursion, and sunset stop at Rick's Cafe—allowing you to experience multiple island highlights in one day. Board a catamaran party boat at Margaritaville and cruise along Negril's coastline, stopping to snorkel at a coral reef and see tropical fish and maybe sea turtles or rays. A domestic open bar on board the boat and hotel pickup and drop-off are included.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
$56.00
From  
$56.00
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NEW TO VIATOR

Private Yacht Hire for Half- or Full-Day Cruise to USVI or BVI

Charter your own private yacht and sail the day away around the U.S. or the British Virgin Islands. Create a custom itinerary with your captain and crew and enjoy a half- or full-day sail out on the crystal clear waters of the Caribbean with your private group of up to 12 passengers. Yachts are equipped with an open bar, light snacks, Wi-Fi, and some water sports equipment.
  • Duration: 4 to 9 hours
  • Free Cancellation
  • Duration: 4 to 9 hours
  • Free Cancellation
From  
$800.00
From  
$800.00
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Catalina Bay and Antilla Shipwreck Snorkel Cruise

Snorkel at Catalina Bay and the Antilla shipwreck during this 3-hour afternoon excursion in Aruba. Board a catamaran and travel to these two excellent snorkeling spots, where you'll swim with angelfish, yellowtail snapper and stingrays. Enjoy drinks from the open bar and snacks on board; round-trip transportation from Aruba hotels is included.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$62.78
From  
$62.78
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Aruba Happy Hour Sunset Sail with Food and Drinks

Watch the tropical Aruban sunset from aboard a 40-foot (12-meter) trimaran on this happy hour sunset cruise. Depart from Palm beach with an attentive captain and crew; relax on board while sipping drinks from the open bar and munching appetizers. Get your camera ready for the colorful sunset and feel free to ask questions about the area and the marine environment.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$49.99
From  
$49.99
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NEW TO VIATOR

Cades Reef Sail & Snorkel Antigua

Climb aboard a catamaran and sail along Antigua's south-west coast. Sit back and relax as we cruise through the warm Caribbean waters to one of the island's best snorkeling sites. Keep your eyes peeled for the palm fringed sandy beaches and neighboring islands. We'll anchor in a beautiful bay near the famous Cades reef. Here you'll snorkel and discover local tropical fish and coral reef. Afterwards the crew will prepare and serve a delicious lunch on-board the vessel before the captain takes you to one of Antigua's 365 beaches. Take some time to relax on the beach and enjoy refreshing drinks served by the crew before sailing back to base.
  • Duration: 6 hours
  • Free Cancellation
  • Duration: 6 hours
  • Free Cancellation
From  
$110.00
From  
$110.00
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Palm Pleasure Sunset Sail

Sail up the coast of Aruba during a colorful Caribbean sunset on this 2-hour excursion. Watch the sun set over the turquoise ocean waters while sipping drinks from the open bar and enjoying light snacks. Meet the friendly crew and dance the evening away on this luxury catamaran. Round-trip transportation from your Aruba hotel is included.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$63.99
From  
$63.99
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