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The only building on sheltered Apantima Bay, this funky beach bar with rooms is one of the reasons the tiny island of Antiparos has suddenly become fashionable. Hanging with the skimpily clad in crowd doesn’t come cheap: If you’re not staying in one of the nine quietly chic suites, you’ll have to fork out handsomely for a sun bed. The payoff is chilling under juniper trees with a detox smoothie, idly watching athletic beach babes paddleboard into the sunset. There’s an alfresco massage and yoga pavilion; a stylish boutique where you can pick up caftans, scents, and sandals; and a 26-foot bar for sundowners and tuna burgers with wasabi mayo.

For a quick bite, drop by the unassuming Ecco Espresso and Gelato. Tucked inside an old adobe building near the Santa Fe Plaza, this airy self-service space has a sprawl of metal tables (inside and out) and a menu of pastries, deli sandwiches (tuna with dill and cucumber), locally roasted coffee, hand-pulled espresso drinks, and spicy hot chocolate. As for gelato, uncover an assortment of 20 flavors including classics like chocolate and vanilla to more unusual, creative scoops like strawberry-habanero, amaretto-peach, and cherry-stracciatella.

Steak house fare meets Caribbean flavors at this outpost of the celebrated international restaurant. Located at the tony Ritz-Carlton, the eatery offers a fusion menu of choice cuts, just-caught seafood, and comfort food sides. Specials incorporate local ingredients such as tuna, snapper, and lobster, but standbys like popovers, Wagyu, and truffle mac and cheese still have top billing. An extensive raw bar, bespoke cocktails, and those famous Aruban trade winds enhance the entire experience.

Crashing waves serve as the soundtrack to your stay at Elbow Beach, situated on 50 lush acres along Bermuda’s rose-hued southern coast. Decorated with exposed beams, tiled floors, and neutral color schemes, the spacious cottage-style rooms are the portrait of coastal elegance—think coral-emblazoned throw pillows, wicker benches at the foot of the beds, and ocean or garden views through French doors. Polished-pebble paths lead the way to the spa, which offers treatments inspired by local ingredients, from a ginger-and-coconut scrub to a hibiscus bath. Grab a rum swizzle in the lounge, relax by the curving perimeter of the pool, or snorkel, swim, and kayak at the hotel’s private beach. You might also prefer to hit the pavement: Elbow Beach is mere minutes from the capital of Hamilton, Gibb’s Hill Lighthouse, and four 18-hole championship golf courses.

Taiwanese chef-owner Ling Huang landed in Shanghai after stints in New York, London, and the Seychelles, and Pirata’s tapas menu reflects her globe-trotting spirit. The octopus salad with chickpeas and fennel appears on nearly every table in the restaurant, as does the platter of mini gyros, palm-size pitas stuffed with shredded steak, onions, and French fries. If you eat seafood, order the clams with Thai basil and the ventresca (tuna belly) paired with a slice of sweet piquillo pepper, drizzled with good olive oil, and served on a slice of baguette. For dessert, go straight for the praline ice cream crepes—squares of sweet and savory ice cream rolled in crushed peanuts, topped with coriander, and wrapped in (yes) a crepe.

Straw Hat, on quiet Meads Bay, is an established favorite with over 20 years to its name. Its creative menu of Caribbean cuisine with a twist will have you returning to this beautiful indoor-outdoor beachfront restaurant. It’s the perfect spot for a meal and an afternoon on the sand, or for watching sports. Try the ceviche of red snapper, the bigeye tuna flatbread, or the grilled crayfish with Anguillan rice and peas, among many other picks.

A chic deli to be sure, Belmondo serves American-style sandwiches like Reubens, tuna melts, grilled cheeses, etc.—about which its young, fashionable adherents rave—but the menu holds some surprises as well, like a barbecued brisket or a chicken curry on peasant bread. The salad selection is varied and creative, in everything from an old-fashioned Cobb to exquisite local beets with goat cheese and avocado. Breakfast (weekends only before 1:45 p.m.) is also about greatest hits; think eggs Benedict and French toast or one of the very few bagels with gravlax you’ll ever see south of the Rio Grande. The place, in Roma Norte, is famed for celebrity sightings and generally crowded, yet the vibe is low-key, cool, and friendly.

Though the beaches of southern Kerala may get more attention, the Malabar coast shores of the northern part of the state are no less beautiful—and offer plenty of their own attractions. Case in point: Bekal Beach, a wide, sandy stretch along the Arabian Sea, set under historic Bekal Fort. The cove-shaped beach offers plenty of room to stretch out and soak up the sun, shallow waters for swimming, and artistic touches like a rock garden, murals, and public sculptures. If you don’t want to get sand in your shoes, take a stroll along the boardwalk, or venture up to explore the Fort complex. Little ones will like the beach’s children’s park, while adults should come back at night, when the beach is illuminated, to enjoy the magical atmosphere. Further along the shores, you’ll spy fisherman bringing in a daily catch that might include mackerel, reef cod, and tuna.

If you’re a major foodie, or if you just want a romantic dinner night, Veya is one of the best picks on Anguilla. Set above Sandy Ground, this home-turned-restaurant serves up Caribbean fusion food in a Moroccan-style lounge, and outdoors on a veranda. The breeze, the candlelit atmosphere, the live music—not to mention the menu (which the restaurant describes as “cuisine of the sun”)—more than make up for not being directly next to the sea. Expect unusual dishes like Moroccan-spiced shrimp “cigars,” grilled jerk-spiced tuna with a rum-coffee glaze, and risotto with basil goat cheese, or try the five-course chef’s tasting menu. Veya is also known for whipping up the best desserts on Anguilla, and the list of options is long.

Irene, a bright and colorful restaurant at the Hotel Savoy, is great for lunch on the sunny bistro terrace outside or for a nightcap sipped on a velvet banquette at the bar inside. The kitchen turns out traditional Tuscan cuisine with surprising modern touches: The classic tomato-and-bread pappa al pomodoro comes stuffed inside ravioli, and the vitello tonnato (veal with tuna-caper sauce) is topped with ribbons of shaved fennel and served with the sauce on the side. On Sundays, the popular “Lunch at Nonna’s” menu is a loving nod to the restaurant’s namesake. Pre- or post-dinner, grab a seat on the terrace, overlooking Piazza della Repubblica, to enjoy wines served in retro-style carafes and bubbly poured into 1950s coupe glasses.

Put on your comfortable shoes and head to the many trails of Cayman Brac to see wildlife, as well as scenic and geological sights. There is a path for all skill sets. Listen to the mating calls of the parrots flying above at the National Trust Parrot Reserve Hiking Loop, or descend carefully into Peter’s Cave and move through the various layers to discover a truly breathtaking natural wonder. Most hotels have a brochure of all the hiking trails; this includes images, difficulty, and a brief description of each trail.

Key West’s most famous literary resident, Ernest Hemingway, lived in this two-story Spanish-colonial villa for nearly a decade and composed several of his best-known works here. His second wife, Pauline, insisted they add a pool to the spacious grounds—the first inground pool in Key West. The cost ballooned to around $20,000, a fortune in the 1930s, and was said to have contributed to the breakup of their marriage. It’s just one of the fascinating stories guides will share on the half-hour tour of the home and gardens (included in the price of admission). And yes, you’re guaranteed to see plenty of six-toed cats, descendants of Hemingway’s original six-toed cat, Snow White.

It’s a crime not to order a cocktail (boozy or virgin) at Spago’s terrace bar, situated next to the famous infinity pool on Marina Bay Sands’ breezy veranda. The drink menu is just as beautifully curated as the decor, featuring more than a dozen original cocktails, over 600 bottles of wine, and an extensive champagne list. Celebrity chef Wolfgang Puck put together the selection of bar bites, including Spago L.A. originals like the bigeye tuna tartare cones. For a full dinner menu in an even more refined setting, book a table in Spago’s glassed-in formal dining room to enjoy dishes like chirashi sushi from the legendary Tsukiji Market and pan-roasted snapper laksa.

Evincing a nautical but contemporary style, this open-air restaurant serves some of the best tostadas in Playa del Carmen. The signature delicacy is a crispy tortilla covered in any number of toppings, and at Las Hijas de la Tostada, expect them to be piled high with just the right blend of sauces and seafood. Try two or three, especially the camarón roca, with shrimp, eel sauce, and a drizzle of pureed chipotle, or raw options like the tostada Uxmal, with tuna and spicy salsa.

Star chef Richard Sandoval recently opened Toro Latin Kitchen + Bar in nearby Punta Ballena. Try the spicy grab quacamole and the beef chicarron with a strawberry basil caipriñha. Get our complete list of Where to Go 2016 vacation ideas here.