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We hopped in a pick-up truck with a bench in the back (aka a Caribbean taxi) & headed toward Honeymoon Beach, St. John. I never would have discovered this hidden beach if it weren’t for the wonders of social media, but thank goodness I did, as it’s possibly the most pristine stretch of sand I’ve ever seen. After a short walk down a dirt road, we arrived at the beach - nearly empty, despite the fact that it was spring break season. Virgin Islands Ecotours has a small stand there where a $49 day pass gets you snorkeling equipment, kayaks, stand up paddle boards, floats & beach chairs. We grabbed a tandem sit-on-top kayak & headed out into the pristine blue water. We paddled up & down the shore, exploring the waters near Caneel Bay Resort, admiring beautiful 50′ sailboats, checking out the National Park Service Head Ranger’s house & beaching our boat on Saloman Beach, where a friendly hiker helped pull us in. Before long, I could feel my legs beginning to get sun burned (& oh did they burn!) under the strong Caribbean sun & we decided it was time for a swim. Decked out in our snorkel, masks, fins & lifejackets, we snorkeled over to some rocks, where we explored the coral reef hand-in-hand. We saw a lot of black & white fish & a few sting rays. We swam back to the beach & lounged for a while before heading back out to snorkel where we saw sea turtles!

Few visitors venture to Duncans Bay, a small town in northern Jamaica, halfway between Montego Bay and Ocho Rios. But its public beach, called Fisherman’s, is one of the best for a local vibe. The scenery is straight out of an old Caribbean postcard: kids play in the distance, colorful fishermen canoes rest on shore, and a ramshackle bar along the wide golden sands attracts the usual neighbors. Show up mid-afternoon, when the grill and some background music get started, while the waves splash and the sun prepares to set. The slow rhythm of this area, away from the resorts, vendors, and tourist trails, will make you want to stay for hours. No problem—there are local guesthouses a stone’s throw away.

Located in South Walton—roughly in between Panama City and Destin on Florida’s scenic coastal route, 30A—Rosemary Beach’s perfect white sand and clear turquoise waters are as close to the Caribbean as Florida comes. Unless there’s a storm a brewing, the Gulf of Mexico waters are delightfully calm and very nearly lake-like, making the beach a favorite for families with young children as well as those who love paddleboarding and kayaking (you can rent gear nearby). And classic Gulf of Mexico sunsets, as you might imagine, are another Rosemary Beach specialty.

Need a break from the hot weather at the beach? Want to unwind and relax in the lap of luxury? Look no further than the beautiful cliff-side Royal Isabela resort. The fresh rum punch is delightful here. It’s one of my favorites on the island (each place has a distinct version). I didn’t ask for the recipe but I’d rather keep it a secret—to keep me coming back to this beautiful place. The resort has a breathtaking view, with private villas and a golf course. I come here to take in the beauty of the Caribbean away from all the crowds and parties. It’s serene and lush.

Located on a craggy cliff jutting between Meads Bay and Turtle Cove Beach, Malliouhana has views of the glittering aquamarine sea that will hypnotize guests from the moment they arrive to its chic porte cochere. The bright, cerulean open-air lobby with mirrored mosaic-tile flooring tumbles out to a deck where tiered infinity pools are punctuated by ruffled yellow umbrellas, and a cliffside restaurant serves fresh seafood and farm-to-table fare. Built in 1984, this is Anguilla’s original luxury resort, which reopened in December 2018 after a complete restoration following Hurricane Irma. While guests may find it hard to take their eyes off the dazzling Caribbean, the 46-room boutique hotel’s interior design offers its own portal to the sublime with an aesthetic that can best be described as tropical eclectic. Guest rooms are painted sorbet yellow or robin’s-egg blue and feature white lacquer four-poster beds, mural panels by Haitian artist Jasmin Joseph, Venetian glass lamps, and sea-green marble bathroom vanities. All of this somehow swirls together for a look that’s both regal and untamed. Beyond the rooms, guests can look forward to an extended pool deck with fresh cabanas, as well as the Bar Soleil, which offers a prime spot to watch Anguilla’s famous sunsets.

James and Connie Roberts, the husband-and-wife team behind Toutant, opened Dobutsu in 2018 with the aim of bringing quality seafood to Western New York. At their Larkin Square spot, the menu highlights American and Asian Pacific fare, with a strong focus on fish dishes like Caribbean jerk snapper and grilled Nova Scotia salmon—though options like Wagyu beef ribs and tomahawk pork tonkatsu are also available. The Hawaiian poke bowls are especially popular, served with either bigeye tuna and sesame soy, or marinated Atlantic salmon and ginger miso. If you’re celebrating something special, opt for the omakase and let the kitchen choose your courses and wine pairings.

Named for its owner’s “poz-itive” vibe, this casual, welcoming restaurant ranks among Dominica’s best. Expect Cajun, Creole, and Caribbean fare in the mix, along with fusion dishes and strong vegetarian options. Menu standouts include callaloo soup, veggie rice, and snapper in coconut-curry sauce, but the lobster, grilled with lemon-garlic butter, tends to steal all the headlines—or at least those not occupied by the fresh juices and home-infused vodkas. Open for dinner only, Poz is quite small in size, so make a reservation to avoid waiting for a table.

The narrow Boca Paila highway runs down the edge of the Riviera Maya in Tulum, dividing the jungle from the sea. Tucked away at kilometer-marker 7.5 lies Casa Jaguar, a haven for the best of both worlds. The restaurant emphasizes Caribbean flavors, using fresh, local ingredients and prepared food and drink with Mexican flair. Try the grilled aguachile seafood cocktail, or the sea bass with corn masa, and wash it all down with a drink of copal mescal, the perfect foil for intense local heat. Beyond being a great restaurant, Casa Jaguar is famous for its “Dinner and Party” concept: there’s a jungle-focused celebration every Thursday with artists and alternative live music.

Near the far northeastern tip of Bequia, the Sugar Reef Café is a breezy spot just steps from the crashing sea. Here, diners can enjoy healthy, locally sourced dishes for both lunch and dinner, from fish roti with mango chutney and papaya-black-bean salsa, to blackened chicken and Callaloo lasagna with Caribbean spinach and rosemary. Sugar Reef’s own estate produces the honey and fruit, while St. Vincent farmers and fisherman are responsible for the fresh produce, meat, and fish. The restaurant even uses coconut milk instead of dairy and coconut oil for frying. Daytime is casual, while evening brings a more romantic vibe.

Even though it’s just 200 yards off the coast of St. Vincent and accessible via a two-minute ferry ride, Young Island feels worlds away from the cares of mainland life. The resort’s 29 guest cottages, which are outfitted with tropical-chic wicker furnishings, stone walls, and louvered windows, provide a plush landing spot after days spent diving among sea turtles and sea horses, hiking neighboring trails to spot the ruins of Fort Duvernette, and swimming up to the Coconut Bar, located on a floating platform 30 feet offshore. Each week, the on-site restaurant serves up Caribbean barbecue favorites like pigeon-pea-and-pumpkin stew, corn fritters, and molasses-glazed wings, making for a delicious stay.

A local institution, the Lobster Pot serves up its crustacean namesakes, among other Caribbean delicacies, on a vista-blessed seaside deck. If you can, arrive at sunset for the nightly tarpon feeding (much more engrossing in person than you’d imagine). And even if you don’t get there exactly at the appointed hour, you can still spot these giants as they continue to patrol the dramatically floodlit waters off the restaurant’s deck for leftovers. As you take in the view, you’ll be eating the likes of lobster-and-mango salad, lobster bisque, or lobster sautéed in a tomatoey, peppery blend and served with fried plantains, rice, and beans.

Nestled in the rain forest leading up to the famous Boiling Lake, Titou Gorge features cool, deep waters and smooth cliff walls formed by molten lava. If you’re wearing water shoes and a flotation device, you can actually get down in the canyon and make your way upstream through a series of pools that ends at a waterfall. If you’ve seen Pirates of the Caribbean: Dead Man’s Chest, then you’ve seen Titou Gorge before—portions of the movie with Orlando Bloom were filmed in this very spot.

Fifteen minutes south of the Puntacana Resort & Club, Eden Roc at Cap Cana is the most exclusive of the six hotels in the gated Cap Cana Reserve. At this Relais & Châteaux property, guests have their choice of beachfront suites with kitchens; stand-alone suites with private pools, gardens, and verandas; and oceanfront villas that come with butler service. Whichever you pick, you’ll also have access to an oceanfront infinity pool, a 30,000-square-foot spa and wellness center, and a private, Blue Flag–certified beach. There’s even a kids’ club in a lagoon-side treehouse for when adults need some alone time.

When hunger strikes, head to La Palapa for seafood and Caribbean fare, or Blue Grill Bar + Restaurant for Nikkei and robatayaki cuisine. Should you want to venture off-property, know that Cap Cana is home to an 18-hole Jack Nicklaus signature golf course. Bespoke helicopter outings, visits to the Punta Espada equestrian ranch, and days at Scape Park (a natural theme park with attractions like zip-lining and cave expeditions) can also be arranged.

One of the great things about the Caribbean is that its rich history was often written at beautiful, easily accessible locations. One of the best places to learn a bit of that history is pictured above. That’s the beach at Columbus Landing in my home island of St. Croix. It was here, in 1493, that Columbus sent ashore a small contingent of his men to scout for fresh water. What they found instead were a group of Indians who weren’t too keen on visitors. What’s the whole story of Columbus and his less than stellar (to say the least) track record throughout the region? That may take a bit more book learning, but feeling what these new visitors may have felt coming ashore in this corner of paradise starts on these sands.

A stroll of St. Kitt’s capital, whether started at Port Zante Marina or the centrally located Independence Square, is an entertaining way to learn more about the island’s past. While the French named Basseterre (it means “low land”), the British are responsible for the town’s most recognizable landmark—the green, cast-iron Berkeley Memorial Clock in the center of the Circus, where several streets intersect. Make sure to visit the area, as well as Independence Square, St. George’s Anglican Church, and the Old Treasury Building, which now serves as the National Museum of St. Kitts. Along your walk, you’ll also find duty-free shops and local boutiques, plus a lively produce market by the waterfront if you come on the weekend.