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Top Caribbean Cruises, Sailing & Water Tours

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1135 Caribbean Cruises, Sailing & Water Tours

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Did you know?You can reserve your spot today and pay when you're ready.
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Did you know?
You can reserve your spot today and pay when you're ready.Learn more

Aruba Happy Hour Sunset Sail with Food and DrinksDay Cruises

Aruba Happy Hour Sunset Sail with Food and Drinks

star-5
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.
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  • 2 hours
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  • Free Cancellation
From  
US$59,99 
From  
US$59,99 
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  • 2 hours
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  • Free Cancellation

Old San Juan Sunset SailDay Cruises

Old San Juan Sunset Sail

star-4.5
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.
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  • 2 hours
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  • Free Cancellation
From  
US$95,00 
From  
US$95,00 
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  • 2 hours
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  • Free Cancellation

Reggae Sunset Catamaran Cruise From Montego BayHalf-day Tours

Reggae Sunset Catamaran Cruise From Montego Bay

star-4
Set sail off the north coast of Jamaica at one of the best times of day—sunset—on a catamaran cruise from Montego Bay. Soak up the island vibes as you sway to the rhythms of reggae music, sip tropical cocktails from the open bar, and take in views of the Caribbean sunset from the water. Your tour includes a stop at Margaritaville Montego Bay for water activities. Plus, hotel pickup and drop-off is provided.
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  • 3 hours
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  • Free Cancellation
From  
US$99,00 
From  
US$99,00 
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  • 3 hours
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  • Free Cancellation

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Sunset Sail by San Juan Historical BayDay Cruises

Sunset Sail by San Juan Historical Bay

star-4.5
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.
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  • 2 hours
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  • Free Cancellation
From  
US$81,03 
From  
US$81,03 
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  • 2 hours
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  • Free Cancellation

Sunset SailSunset Cruises

Sunset Sail

star-4.5
Sail aboard a luxury catamaran on this sunset cruise from Aruba. During this evening excursion, enjoy tropical cocktails as the sun dips below the horizon and the stars appear. Cruise up Aruba's stunning coastline and enjoy views of Palm Beach while snacking on complimentary appetizers. Get to know the boat's crew as it entertains you with storytelling, local music, and dancing.
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  • 2 hours
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  • Free Cancellation
From  
US$61,99 
From  
US$61,99 
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  • 2 hours
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  • Free Cancellation

Old San Juan Harbor SailDay Cruises

Old San Juan Harbor Sail

star-4.5
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.
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  • 1 hour 30 minutes
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  • Free Cancellation
From  
US$59,00 
From  
US$59,00 
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  • 1 hour 30 minutes
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  • Free Cancellation

Chukka's Catamaran Cruise to Dunn's River Falls from Ocho Rios or Montego BayDay Cruises

Chukka's Catamaran Cruise to Dunn's River Falls from Ocho Rios or Montego Bay

star-4.5
Sail through the Caribbean aboard a catamaran to the place where Dunn's River Falls empties into the sea. Stop to snorkel among schools of tropical fish and living coral. At Dunn's River Falls, climb the terraced pools to the top of the falls for spectacular views of the surrounding landscape. On the return catamaran voyage, enjoy rum punch and island music. Lunch, snorkel equipment and round-trip transportation from Ocho Rios or Montego Bay hotels are included.
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  • 8 hours
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  • Free Cancellation
From  
US$129,00 
From  
US$129,00 
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  • 8 hours
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  • Free Cancellation

Reggae Catamaran Cruise from Montego BayHalf-day Tours

Reggae Catamaran Cruise from Montego Bay

star-4.5
Dance to reggae rhythms and enjoy the cool blue Caribbean on this ‘floating party’ catamaran cruise, including stops to snorkel at a protected reef and join the lively scene at Margaritaville. Back on board, a DJ, unlimited drinks from the open bar, and Jamaican-style appetizers keep the energy going as you soak up stellar views of the island’s north coast. 
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  • 3 hours
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  • Free Cancellation
From  
US$99,00 
From  
US$99,00 
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  • 3 hours
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  • Free Cancellation

5-Hour Small-Group Catamaran Cruise from Bridgetown with LunchDay Cruises

5-Hour Small-Group Catamaran Cruise from Bridgetown with Lunch

star-5
Cruise on the Caribbean Sea aboard a catamaran for a 5-hour trip with a small group. Go snorkeling with sea turtles, explore shipwrecks, and enjoy the included use of snorkel equipment. Sip drinks from the onboard bar, refuel with an all-you-can-eat buffet, desserts, and tapas. This small-group tour is limited to just 12 people to ensure personalized attention from your guide. Round-trip hotel transport included.
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  • 5 hours
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  • Free Cancellation
From  
US$144,94 
From  
US$144,94 
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  • 5 hours
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  • Free Cancellation

Luxury Wine & Dine Dinner SailWine Tasting & Winery Tours

Luxury Wine & Dine Dinner Sail

star-4.5
Set sail from Aruba for a dinner cruise by catamaran, then watch the sun set into the Caribbean as you drink and dine on deck. Enjoy an open bar throughout the cruise, and nibble local and international fare from a sumptuous, three-course buffet. Take in Aruba’s shoreline scenery and cool sea breezes, then return to Palm Beach as the stars appear over the island. 
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  • 3 hours
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  • Free Cancellation
From  
US$111,52 
From  
US$111,52 
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  • 3 hours
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  • Free Cancellation

Sunset SailDay Cruises

Sunset Sail

star-4.5
At sunset, the Caribbean’s warm breezes complement stunning views. Take in the experience aboard a 54-foot catamaran sailboat complete with appetizers and alcoholic and non-alcoholic beverages. The trip is ideal for families, couples, and groups. You’ll return to the Marriott's Frenchman's Cove Dock in time for dinner.
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  • 1 hour 30 minutes
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  • Free Cancellation
From  
US$46,16 
From  
US$46,16 
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  • 1 hour 30 minutes
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  • Free Cancellation

All Inclusive Afternoon Sunset Snorkel TourSailing Trips

All Inclusive Afternoon Sunset Snorkel Tour

star-4.5
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.
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  • 3 hours 30 minutes
From  
US$70,77 
From  
US$70,77 
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  • 3 hours 30 minutes

Negril & Ricks Cafe Sunset Catamaran CruiseDay Cruises

Negril & Ricks Cafe Sunset Catamaran Cruise

star-4
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.
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  • 3 hours 30 minutes
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  • Free Cancellation
From  
US$71,00 
From  
US$71,00 
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  • 3 hours 30 minutes
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  • Free Cancellation

Sandy Toes Full Day Excursion to Rose IslandDay Cruises

Sandy Toes Full Day Excursion to Rose Island

star-4.5
Cruise to the pristine Rose Island during this trip from Nassau. On this half-day excursion, relax on the remote beach, participate in group activities or snorkel in the calm, turquoise waters. Enjoy a welcome cocktail aboard the boat, then go kayaking, play beach volleyball or explore the island on foot before indulging in a delicious buffet-style lunch.
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  • 6 hours
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  • Free Cancellation
From  
US$131,00 
From  
US$131,00 
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  • 6 hours
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  • Free Cancellation

St Lucia Full-Day Catamaran Sightseeing Cruise With SnorkelingDay Cruises

St Lucia Full-Day Catamaran Sightseeing Cruise With Snorkeling

star-4.5
Cruise around St Lucia aboard a catamaran named 'Tout Bagay' during this 8-hour excursion. With an expert captain and crew as your hosts, spread out on the deck for some sun and relaxation while sipping rum drinks from the open bar. Go ashore to explore sites like Morne Coubrail Estate (where you can opt to go ziplining), the sulphur springs, Toraille Waterfall and the quaint town of Soufriere. Use the provided snorkel equipment to explore the underwater world in Anse Cochon and Marigot Bay. Enjoy a Creole-style buffet and round-trip transportation from your hotel.
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  • 8 hours
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  • Free Cancellation
From  
US$125,00 
From  
US$125,00 
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  • 8 hours
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  • Free Cancellation

Montego Bay Catamaran Cruise and Snorkeling Tour from Montego BayHalf-day Tours

Montego Bay Catamaran Cruise and Snorkeling Tour from Montego Bay

star-4
Enjoy a fun-filled day aboard a luxury catamaran during a sailing adventure from Montego Bay. After pickup from your hotel, board a catamaran for an unforgettable day of drinking, dancing, and socializing with other partygoers. Opt to swim and snorkel in the warm Caribbean waters or relax on the catamaran's deck with a drink from the open bar. A stop at Jimmy Buffet's Margaritaville is also included.
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  • 4 hours
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  • Free Cancellation
From  
US$121,75 
From  
US$121,75 
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  • 4 hours
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  • Free Cancellation

Half-Day Aruba Special Champagne Brunch CruiseDay Cruises

Half-Day Aruba Special Champagne Brunch Cruise

star-5
Combine a snorkeling excursion at Aruba's best snorkel spots (such as the sunken SS Antilla) with a Champagne brunch on this half-day cruise. Even beginner snorkelers can feel safe and comfortable given the snorkeling instruction and all included equipment. Brunch includes fresh food and pastries, as well as an open bar.
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  • 3 hours
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  • Free Cancellation
From  
US$79,99 
From  
US$79,99 
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  • 3 hours
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  • Free Cancellation

Caribbean Dinner SailSailing Trips

Caribbean Dinner Sail

star-5
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.
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  • 2 hours 30 minutes
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  • Free Cancellation
From  
US$87,83 
From  
US$87,83 
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  • 2 hours 30 minutes
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  • Free Cancellation

Negril Beach & Catamaran Cruise with Ricks CafeDay Trips

Negril Beach & Catamaran Cruise with Ricks Cafe

star-3.5
Cruise along the coast of Jamaica to the waters off Rick's Cafe in Negril. Snorkel off the boat among coral and tropical fish or just stretch out on the boat's deck and sunbathe during this excursion from Negril. Enjoy unlimited drinks and reggae music while you watch the gorgeous Jamaican sunset from this luxury catamaran.
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  • 4 to 12 hours
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  • Free Cancellation
From  
US$75,00 
From  
US$75,00 
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  • 4 to 12 hours
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  • Free Cancellation

Jolly Pirate Morning Sail and Snorkel Cruise in ArubaDay Cruises

Jolly Pirate Morning Sail and Snorkel Cruise in Aruba

star-4.5
Spend four hours on the water during this Aruba pirate cruise. Aboard an 85-foot (26-meter) teak schooner, you'll travel to three 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.
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  • 4 hours
From  
US$73,68 
From  
US$73,68 
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  • 4 hours

Sxm Luxury Catamaran Group Tour(cruise ship or sxm customers)Day Cruises

Sxm Luxury Catamaran Group Tour(cruise ship or sxm customers)

star-5
Spend the day cruising along St. Maarten’s shores on a luxury catamaran. Booking this tour in advance means you’re guaranteed some time out on the water, taking in the coastal sights, swimming, and snorkeling at your leisure. You’ll post up off of Maho Beach to see the planes take off and land, go fishing or kayaking, and enjoy lunch on board midday.
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  • 6 hours
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  • Free Cancellation
From  
US$186,00 
From  
US$186,00 
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  • 6 hours
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  • Free Cancellation

Catamaran Snorkel and Picnic CruiseDay Cruises

Catamaran Snorkel and Picnic Cruise

star-5
Get a taste of island life during this full-day catamaran cruise and snorkeling trip to a nearby nature reserve, where you 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.
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  • 8 hours 30 minutes
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  • Free Cancellation
From  
US$83,00 
From  
US$83,00 
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  • 8 hours 30 minutes
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  • Free Cancellation

Aruba Sunset Cruise and Seaside DinnerHalf-day Tours

Aruba Sunset Cruise and Seaside Dinner

star-4.5
Enjoy picture-perfect views on an Aruba sunset cruise followed by a seafood dinner at a waterfront restaurant. Set sail aboard a catamaran for a cruise on the Caribbean while you take in the vivid colors of a tropical sunset. Enjoy snacks and an open bar before a steak or fresh fish dinner served seaside with a glass of wine at the Pelican Nest Seafood Grill.
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  • 3 hours
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  • Free Cancellation
From  
US$97,44 
From  
US$97,44 
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  • 3 hours
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  • Free Cancellation

Cruise to SaintesDay Cruises

Cruise to Saintes

star-5
The Saints - Board a motor catamaran from Pointe-à-Pitre to set sail for the Saintes archipelago (Terre-de-Haut, Ilet Cabri & Terre-de-Bas) with Simon, a young passionate skipper always smiling! A complete program, and a friendly atmosphere GUARANTEED! Drinks & meals included / Masks & snorkels included
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  • 9 hours
From  
US$142,07 
From  
US$142,07 
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  • 9 hours

Frequently Asked Questions

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What are the best Cruises, Sailing & Water Tours in Caribbean?

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