The Ultimate Top 5 “Boat to Dinner” Caribbean Destinations

Ever considered actually sailing off into the sunset?

It’s no secret that the Caribbean offers some of the most beautiful vacation destinations in the world. With at least 28 island nations and more than 7,000 individual islands, the problem quickly becomes deciding where to go. One thing is certain: the best way to explore the Caribbean’s world-renowned beauty is from the water.

Each of the islands offers a variety of local flavors—a preference for cumin in Cuba, or curry along the English islands. Experience island culture while enjoying delicious Caribbean cuisine with our unique insider’s guide.  What’s so unique about it? These restaurants are meant to be accessed by boat. Here is the low-down on five of the hottest, most delicious, boating destinations in the Caribbean.

British Virgin Islands

Arrive at the tiny, remote island of Jost Van Dyke by boat or private charter. At just 3.5 square miles, Jost Van Dyke is the smallest of the four main islands of the British Virgin Islands.  Despite its size, the island is rich in history and was once home to the Arawak Indians.  Spend the day exploring the grounds and trace the old trails that connect the island, or discover the lush ruins of sugar mills. Whale and dolphin watching are popular in the fall and winter months.

Where to dine: Foxy’s Bar may well be the best known bar among boaters in the Caribbean. Foxy’s serves unique, Caribbean style dishes and a la carte dinner Sunday through Thursday. Sly Fox and Dread Fox are the specialty drinks of the house made with Foxy’s house-made rum. Draft beer fresh from Foxy’s own microbrewery, and featuring smooth Caribbean hops, are also popular refreshments.  Check Foxy’s Bar calendar of events for upcoming happenings and pictures of previous events.


With a past steeped in marine tradition, sailing has been a central part of Antigua’s culture for ages.  Constant trade-winds and various scenic harbors make the coasts of Antigua ideal for yacht cruising. On land, the picturesque island offers plenty of opportunity for shopping and dining. The historic English Harbor is a favorite spot among yachters.

Where to dine: OK, so dining is a bit of a stretch here. But if you’re looking for a fun family-friendly way to spend a great day on the water, look no further than D-Boat in Antigua. D-Boat is a retired oil tanker that was converted into a water park (yes, you read that correctly) for “kids” of all ages. The massive floating entertainment center features waterslides, trampolines, and swing ropes, as well as a full bar and bistro.  Nearby attractions include snorkeling tours and the top-rated Stingray City, where you can pet and feed Southern Stingrays in clear shallow waters.  


Experience the ultimate yachting adventure on the shores of Grenada. A wealth of sheltered anchorages and year round warm weather make these waters a perfect sailing destination.  Grenada also provides an excellent base from which to visit Carriacou, Petite Martinique and the rest of the Grenadines.

Where to dine: Anyone who has been to Happy Island in the Grenadines raves about the warm service and delicious BBQ. This small, man-made key serves legendary island BBQ and well-crafted rum cocktails year-round.


We’ll cut right to the chase—Cuba has clearly had its fair share of issues over the past few decades.  But with long-standing restrictions now lifted, and the island offering some of the most remarkable waterways and sought-after cuisine in the Caribbean, its inclusion in this guide is well-earned. Cuba currently welcomes sailors on both private and chartered vessels, but be sure to verify requirements for docking and local restrictions.

Where to dine: Visit San Cristobal Paladar in Havana for traditional Cuban cuisine and impeccable décor. Of course, everything on the island is ancient, but at San Cristobal Paladar you will find some of the coolest antiques in Havana, including vintage clocks, chandeliers, furniture and photographs. The place has significantly picked up steam in recent months as it has catered to celebrities and even a certain president. After a delicious meal, dance the night away to the pulsing beat of afro-jazz in the basement lounge of La Zorra y el Cuervo before setting off into the sunrise.    


Sailing in Anguilla is not just a popular pastime; it’s the island’s national sport. Anguilla is known for hosting a variety of annual summer racing events that attract large crowds from all over the world.  Race after-parties and celebrations are common on the island. Boaters seeking more private waters will discover perfect tranquility just north of the island in the waters of Prickly Pear Cay and Dog Island.

Where to dine: Sandy Island is a small cay just off Sandy Ground beach in Anguilla. What started as little more than a make-shift shack with a drum-pan barbecue grill has become a backdrop for countless, movies, photo shoots and music concerts. Sandy Island currently offers a wide lunch menu including lobster, grouper, snapper, crayfish and ribs. Visitors can bury their toes in the soft white sand while enjoying a delicious no-fuss meal.

Reserve your Caribbean boating adventure today!

Boatsetter has fleets of boats available to help you embark on your Caribbean getaway.  With a variety of boating and sailing options available, Boatsetter has you covered. Whether you’re looking for a catamaran, trimaran, schooner, or other personal watercraft, Boatsetter has everything you need to embark on your Caribbean adventure. Reserve today, then pack your swimsuit and get ready to experience the splendor of the Caribbean!

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