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Two of the cooks who worked with me at Nahm in London opened a dinner-only spot named Bo.lan. Bo and Dylan prepare traditional but often hard-to-find dishes, such as stir-fried chicken thighs with bamboo shoots, and red curry of pork hock. —David Thompson

Bowens Island Restaurant has existed in one form or another since 1946. The original building, covered in Sharpie messages scrawled by diners over the years, burned to the ground in 2006. Owner Robert Barber rebuilt it almost immediately, all the while serving steamed oysters straight from the inlet beyond the dock. Today, the paper plates are modest but come piled high with fried seafood, fries, and hush puppies. Order the oysters, top them with cocktail sauce, and wash it all down with a local beer for one of the best dining experiences in town. Bowens may not have white linen tablecloths or awards hanging on the walls, but this is where you want to be eating in Charleston.

For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

Thriving marine life and crystal-clear water make Curaçao an unforgettable snorkeling destination. At Tugboat Beach, you can head 17 feet below the surface to explore a sunken vessel. Mushroom Forest is known for its hard corals and cute (creepy?) critters. And at Playa Grandi, you can watch turtles glide close to shore while fishermen clean catch every afternoon. Dance with the fish along PortoMari beach, or plunge deeper to explore its double reef system. Dive shops abound for PADI classes or equipment rentals—get ready to merge with Mother Nature.

Smack in the center of Willemstad, the Renaissance Curaçao is adjacent to the historic Rif Fort shopping and entertainment complex and within walking distance to everything downtown. It solves for not having beach access with two infinity pools overlooking the ocean and cruise pier, each edged in a man-made, sandy beach that can pass for the real thing at first dip. The colorful lobby is connected to a casino, mall, and the island’s only Starbucks. Be sure to check the local cruise schedule before booking an ocean-view room, as you may have your vistas blocked by a ship. You may also want to rent a car to explore the island’s natural beaches but, come nightfall, it’s easier to walk to the Punda and Pietermaai districts for dinner.

In addition to its beaches, Aruba’s gambling culture is one of the island’s biggest draws, with most casinos located in the large hotels of Palm Beach and downtown Oranjestad. Stellaris, in the Aruba Marriott Resort, is one of several glittering options that stay open 24 hours a day. The sprawling floor boasts rows of slot machines and 26 tables, offering all manner of poker, craps, and blackjack games. Visitors can also look forward to bingo, sports kiosks, and a VIP club for high rollers. Note: Aruba’s casinos are restricted to those 18 and older.

Also known as Old Navarino Castle, Paleokastro—built by the Frankish ruler Nicholas II de St. Omer around 1278—is located above Voidokila Beach in Messinia’s Mediterranean area. Make sure to bring your camera, as a trek to the castle awards panoramic views of the Ionian Sea, the city of Pylos, Voidokilia Bay, the Romanou-Petrochori beaches, Gialova Divari lagoon, the olive tree-lined Peloponnesian Hills, the Sykias chanel, Sphacteria island, and Navarino Bay. When hiking, you’ll be taking the same path as you would to reach Nestor’s Cave, a popular cave in Greek mythology.

In swank St. Barth’s, it’s hard to imagine that it’s only the Gucci-clad glitterati that live here. In an effort to see for myself, I rented a jeep and on a quiet Sunday morning drove around the island. I stopped at L’Orient Beach where my question was answered. Families played in the turquoise sea, suntanned, surfed, ate sandwiches while leaning against the colorful surf shack. It was the antithesis of the rosé-fueled scene at Nikki Beach on the other side of the island. I sat and watched for an hour, trying to take photos, but slipped away, feeling very much the interloper.

Always a crowd, but how could it be otherwise? Shore panoramas frame breathtaking nature, turquoise seas and sugary, white sand. Mighty close to the perfect beach, dreamy and hot, with great sightseeing opportunities. Keep eyes peeled for jumbo starfish and other marvelous creatures, now a main beach attraction. The shopping’s good, too, especially for artisanal handicrafts and dishware.

We were lying in the sand in Vieques. We’d been told to watch out for horses, but nothing could prepare me for this. What a majestic experience to see wild horses free on the sands of Sun Bay Beach.

Within Miami‘s most famed Fontainebleau Hotel is an gastronomic superpower, but it’s the mixology by bartender Hector Aceveda that really sets the eatery apart. Try some of the innovative cocktails using food products and specialty preparation. A great alternative to the pool bars and nightclubs.

Pier 1’s greatest appeal is its setting: The open-air restaurant and nightclub occupies a pier that extends out into the Caribbean in Montego Bay. By day and into the early evening, the restaurant draws visitors and locals interested in a good meal with a stellar water view. At night, regular parties start late and run into the wee hours of the morning. Skip the noisy chain restaurant-bars down the street and try something more Jamaican, instead.

Take a two-hour dinner cruise along the Rhône River aboard the charming Mireio, the largest panoramic restaurant boat in the region. On the Saint Bénézet Cruise, you’ll pass the most beautiful sites in Avignon—from the famous Pont d’Avignon and the quays along the Rhône to the Palais des Papes, the clock tower, and the Rocher des Doms—all while enjoying delicious dishes like duck with Provençale herbs and seasonal vegetables, and fillet of beef with jus au Châteauneuf-du-Pape. For something even more lively, you can opt for the Dinner Entertainment Cruise, which includes dancing on board until 1 a.m., or the Dinner Show Cruise, complete with a candlelit dinner and Brazilian entertainment. There are also lunch cruises, though they’re often more crowded than the dinner options.

In Greek mythology, Heracles slew all the sons of the King of Pylos except Nestor, who became king of Pylos himself. Nestor appears as a sage elder in both the Iliad and the Odyssey, expounding on how things were really tough back in his day. If you visit Voidokilia Beach, about 12 kilometers (7.5 miles) from Pylos, you can take a 15-minute walk to see Nestor’s Cave. First, enjoy your time on the beach, which is renowned for its natural beauty. Then climb over the dunes at the beach’s southwest end and follow the hillside path to the cave, which sits just below the ruins of the Paleo Kastro, the old Pylos castle. As legend has it, this cave is where Hermes hid the 50 cattle he stole from Apollo. The trip is worth it for the views alone: The higher you go, the more you’ll see, as the panorama takes in Voidokilia Bay, the Gialova lagoon, the Bay of Navarino, the Peloponnesian hills and the city of Pylos.

Rekondo is a little hidden treasure of a restaurant, started by an aficionado of wine. A real aficionado. His varied collection means the restaurant has a wine list of hundreds of pages. These are wines critics dream about, at prices that are a fraction of the cost in other parts of the world. They are so well-priced, in fact, that the restaurant only allows bottles to be taken off the premises if they are opened. On the outskirts of town, it is rarely completely booked and has a spacious terrace that is absolutely perfect for having a bottle of wine at sunset.