Courtesy La Cabane de l’Isle

Luxury is a lifestyle on impossibly cool St. Barts, and there’s no better place to experience the island’s legendary people-watching, fashion-spotting, and off-the-charts gastronomy than this on-the-beach, lunch-only restaurant at Cheval Blanc St-Barth Isle de France, a sublime five-star hotel of LVMH pedigree. Bury your toes deep in the sands of dazzling Flamands Beach for a light lunch of salad, fish crudos of locally caught wahoo, and fruit-forward libations with your newest A-lister friends.

Courtesy El Farallón

Immerse yourself in Los Cabos’ iconic desert-meets-sea landscape at this seafood-centric restaurant, which can be found in the cliffside The Resort at Pedregal. Dine al fresco under starry skies as ocean waves crash at your feet, choosing from an ever-changing selection of fresh catch from the restaurant’s old-fashioned fish market; your selection is then prepared to order. Begin or end the evening on the adjacent Champagne Terrace, where champagne selections are served by the glass and paired with either housemade moles or mineral salts linked to the soils from which the champagne was first created. (These unlikely pairings are intended to highlight the champagnes’ distinctive mineral and fruit components.)

Sandy Island, Anguilla

Off the Anguilla mainland, Robinson Crusoe fantasy and foodie fantasia unite on a spectacular speck of sand, with just enough room for a restaurant shack, some two-dozen lounge chairs, and a 360-degree beach (the size of which depends on the tide). You’ll quickly discover that Sandy Island’s eponymous beach shack serves up the best BBQ crayfish in Anguilla—and a killer rum punch to wash it down. Arrival is by private boat or the island’s daily water shuttle, all subject to a (sometimes very) wet landing.

Bayside Restaurant, St. Lucia

This al fresco restaurant at Sugar Beach, A Viceroy Resort sits amid the splendor of the Caribbean’s most extraordinary topographical phenomenon: the nexus of Gros Piton and Petit Piton, a duo of lush, towering mountains rising dramatically from the crystalline shallows of Anse des Pitons. Lunch on thin-crust pizzas from the wood-fired oven (we love the pesto-based Pizza de Mari Sainta Lucia with shrimp, calamari, scallops, red onion, and peppers) or come for dinner to indulge in heartier St. Lucian fare like Balenbouche conch stew.

Courtesy COMAL

Sip on “Chilenitos” (mezcal, poblano pepper liqueur, pineapple, and ginger) and feast on innovative Baja cuisine like steamed sweet potato-wrapped snapper, overlooking picture-perfect Chileno Bay at the signature restaurant of Los Cabos’s newest luxury hotel—and the latest addition to Auberge Resorts Collection—Chileno Bay Resort & Residences. You can also own a villa and still be a part of the community – info here.

There are many a fabulous spot to enjoy sea views while dining in the chic, open-air eatery; but for sunset aperitifs, our favorite nook is around Comal’s cantilevered fire pit, where celebrity mixologist Osvaldo Vasquez shakes and stirs exceptional artisan cocktails rich in Mexican influence, including his signature T&T Margarita and “Mexican moonshine.”

Topless women drink for free, by the way.

We admit it: downing cheap drinks at Sunset Bar & Grill and watching planes nearly scrape our heads as they land at Princess Juliana International Airport is a veritable St. Maarten guilty pleasure we’ve indulged in on more than one occasion. However, when we’re not re-living our youth, our go-to spot on the island is the Beach Bar at Belmond La Samanna, St. Martin, the island’s most coveted resort. Located on a secluded and serene cove, this is the superlative spot for enjoying the ultra-turquoise waters of the French-Dutch island—all with a pricey glass of French wine, of course.

Thanks to a sizable yachting community, beach barhopping between islands is a favorite local pastime on the British Virgin Islands. And while there are indeed many sandy watering holes from which to choose, the undisputed king of the BVI scene remains the circa-1970s Jost Van Dyke legend: the aptly named Soggy Dollar Bar. Anticipate a few rounds of potent rum-forward Painkillers—the drink was supposedly invented here—and complete the rite of passage of swimming to shore to pay with soggy dollars (though today’s bar tabs may require soggy twenties or hundreds).

Read it at Conde Nast Traveler

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