Barbados

These spacious, coral-stone cottages are spread across tropical gardens on the west coast of Barbados. The air-conditioned rooms offer total privacy, and the larger villas—three- and four-person suites—are each equipped with a plunge pool, kitchen, and a lounge and dining area. The interiors feature traditional fretwork, rustic wood furnishings, comfortable beds, and cream-hued linens. The property has been run by the same family since the 1950s—the O’Haras—who know the ins and outs of their seaside villas well enough to intuit the needs of their frequently returning guests. Acting more as hosts than managers, they open their home to guests every Monday night for a cocktail party and outdoor BBQ buffet.

Cobblers Cove reminds us of a tropical country club: Keep the pastels, vintage florals, and starched white linens of a Slim Aarons photograph, but add in the warmth of a friendly staff, a gorgeous sea view, and a stiff rum punch. The 1940s mansion has drawn guests through its powder-pink walls for decades, thanks to the impeccable service and a restaurant often hailed as the best on the island. The charming room décor includes white bamboo seating, Egyptian cotton bed linens, goose-down pillows, and an absence of televisions. Stimulation comes the old-fashioned way: a jaunt on the easily accessible beach, where snorkeling reveals turtles darting among coral, or an indoor game of chess or checkers inside the wood- and leather-accented dining hall. Time dinner to catch the sunset, when the golden light illuminates the walls of the Camelot restaurant, where Bajan chef Jason Joseph grills the catch of the day to perfection.

Between the rocks of a jaw-dropping cliff, the flicker of torches and candelabras, and the sound of crashing waves, it’s hard to believe anyone remembers what’s actually on their plate when they dine here. But chef Paul Owen does an impressive job of reminding the guests—with his seafood-ruled menu of shrimp ravioli with pesto and tomato fondue, crab cakes in coriander cream, and fresh catch of the day.

There are breathtaking sea views all over Barbados, and still, the one at Champers feels special. With floor-to-ceiling glass windows lining the dining hall, waves practically crash on the floor. The food, a mix of seafood and meat infused with Caribbean flavors, includes shrimp and mango salad, crab crepes, and an upscale take on the local classic, Bajan fried flying fish. Don’t miss the art gallery upstairs, which features a selection of pieces for sale from the island’s local talent.

Once you book, you are assigned to someone that basically looks after you throughout your trip. Your ambassador will do everything from picking you up at the airport, to getting you a rum punch, to setting up ‘jet lag revival’ massages upon arrival and arranging private dinners on the beach. Complimentary ice cream (we hear the house rum raisin is pretty insane), water and fruit by the pool and champagne breakfasts are nice perks. It’s a small place with only a handful of rooms and is adults only—so best for a couple.

Though it lacks the glitz and grandeur of its high-end counterparts, Round House Inn is a worthy Barbados destination in its own right. Housed in a majestic, 19th-century colonial building overlooking the famous “Soup Bowl” break (legend has it, Kelly Slater caught some of the best waves of his life here), Round House features uninterrupted views of the Atlantic coast. Owners Robert and Gail Manley took great care to outfit each of the four natural coral-block guest rooms in subtle earth tones and wooden antiques, allowing the original architecture (skylights, deep-set windows) to take the spotlight. The no-frills atmosphere is undoubtedly inviting, but the main draw of this beachfront oasis is the eponymous Caribbean restaurant, which has locals, tourists, and guests flocking to its outdoor patio in droves. The homemade banana bread, Bajan pumpkin fritters, and flying fish and breadfruit soup—a wonderfully fragrant national dish—are not to be missed.