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Since its opening along a dazzling stretch of sand known as Cabbage Beach in 1962, The Ocean Club on Paradise Island has been the preferred stay of old-money patriarchs and traditionalists. Though much at the serenely posh resort has remained unchanged, the 105-room property has been modernized to meet today’s standards with spa-sized marble bathrooms, sweeping WiFi, and a restaurant run by star chef Jean-Georges Vongerichten. But it’s the feeling of a privileged, unhurried yesterday that continues to draw an appreciative upper-crust crowd. An on-site tennis pro provides tips for improving your backhand, Versailles-inspired gardens complete with a 12th-century Augustinian cloister offer moments of quiet contemplation, and rounds of golf end with martinis at the resort’s bar. These details, plus knowing that a personal butler and afternoon champagne and strawberries are included in the price, keep guests returning year after year.

This, the bar lauded for the city’s best sliders, has just added another star to its menu: Neapolitan pizza. Regulars are mighty keen on “carbo pepe,” by Chef Miwi (at the helm in this kitchen as well as at acclaimed hipster-heaven Belmondo, both in Roma). Félix remodeled a porch into a garden where they’ve got salads, pastas, and the aforementioned pies. These and other dishes took the chef to Italy, for expert education, leading to experimentation and that perfect dough. Super-chill and friendly, yet the service could hardly be improved.

Giving new life to an old haunt, the Cayman Spirits Company has turned the onetime bar area of the historic Pedro St. James into a rum-centric saloon and café: the Outpost Bar. Go for a tasting, and you’ll try as many as five local rums, one of which—the 1780—is aged and available exclusively on-site. The next most important variety to sample here is the Seven Fathoms, if only so you can say you’ve tasted rum that’s been anchored and aged 42 feet (i.e., seven fathoms) below the Caribbean’s surface. Of course, considering the Outpost’s view—prime, uninterrupted seascape—you could have pretty much any drink in hand and be happy.

The surprises at this excellent Italian restaurant in Disney Springs start right when you arrive and gaze upon the airy dining room. Complete with 50-foot-high ceilings, a grand staircase, and sweeping views over Lake Buena Vista, it’s themed after an abandoned airline terminal, with lots of fun travel touches that include a vintage-style glove dangling like a giant chandelier overhead. Chef Theo Schoenegger is a native of Italy, and his menu spotlights specialties from Rome and Sicily. Delicious Italian cheeses and cured meats are perfect starters for sharing. And signature dishes include Sicilian arancini di carne (rice balls with meat) and a spiral pasta dish topped with crab called busiate con granchio. Italian red, white, and Prosecco wines star on the well-informed wine list. And don’t miss a plate of cannoli to share for a sweet finish.

Duffy’s calls itself a “bar that serves great food.” Its brand of fruity tropical cocktails (some served in ceramic skulls) and casual fare seems somehow perfect for a relaxing Caribbean vacation. The restaurant claims to have hosted “pirates, debutantes, nerds, and rock stars.” From the outside, Duffy’s looks unassuming, but inside the colorful tiki bar decor features standard elements, such as bamboo-pole siding, spruced up with maritime mementos from around the Caribbean.

Award-winning Nautilus offers seasonal cocktails, over 20 wines sold by the glass, and an extensive list of mezcal, beer, and sake. Warm and friendly, this is the kind of place where you’ll no doubt meet the folks sitting next to you at the bar. Owned by a threesome who know their way around the industry, the lively, hip scene almost feels like you’re at a cool friend’s cocktail party.

Just steps from the sea, on the pine-shaded terrace of the Cheval Blanc St. Tropez (formerly La Résidence de la Pinède hotel), the Vague d’Or celebrates the riches of the sea. Chef Arnaud Dockele’s passion for the region is evident in each bite—and Michelin inspectors have given three stars to the kitchen to reward his creativity in dishes like spider crab in a citrus bath; a verbena-infused bouillon; and abalone served with locally grown onions. Pastry chef Guillaume Godin picks his inspirations from nearby orchards with desserts based on apricots and almonds and local lemons that make the perfect end to a meal under the stars.

Quinto La Huella is the second location of arguably Uruguay’s most famous and best restaurant, the Parador La Huella in the tiny resort town of José Ignacio. On the fifth floor of the East, Miami, hotel, the eatery uses a wood-fired parrilla (grill) and oven to cook nearly everything on the menu. The dining room is wrapped in wood, and the outside dining area is a garden oasis with leafy foliage, great music, and a homey vibe. The burrata, served with fresh figs, prosciutto, and walnuts, is a standout starter, and don’t forget to order smashed potatoes, which are served as they are in Uruguay: The potato is grilled over the fire and smashed right before serving, to retain the natural texture of the vegetable.

My favorite way to start a day in Tianzifang is with a hearty breakfast at Kommune. With a notably large courtyard, it’s a fabulous place to kick off a warm-weathered day and even if you’re a little chilly, the coffee comes in bowl sized mugs that will warm you right up. Open from 7am-1am daily. (They also have a great wraps at lunch and a happy hour from 5pm-7pm.)

While South Africa isn’t known for its sushi, you can easily satisfy your craving in Cape Town at Willoughby & Co. The menu at this waterfront restaurant is encyclopedic—there’s everything from Boston clam chowder and spaghetti marinara to prawn curry and teriyaki chicken ramen, but sushi is the star. Try the chili-seared tuna sashimi or the tuna roll with caviar sesame seeds.

Watch local artisans weave handmade baskets, hats, and bags from local grasses and palm fronds using traditional methods at the Middle Caicos Co-op. This nonprofit center helps support the local community on Middle Caicos and keeps Caribbean crafting traditions alive. Visitors stopping by the studio, located in Conch Bar, will often find a handful of the co-op’s 60 artists on site, happy to demonstrate their process and answer questions as they work on their pieces. Along with woven items, you’ll also find model sailboats, jewelry, and other handicrafts.

La Terrasse, the most refined rooftop bar in Paris, attracts a well-heeled crowd who want the view without a fuss. White umbrellas provide shade over the spacious tables on this romantic rooftop garden with rose-lined alcoves and iconic views of the Eiffel Tower, an altogether peaceful place to enjoy a champagne cocktail and watch the sun set. As dusk inches into evening, consider dining at the bar’s prix fixe restaurant—the small menu of seasonal dishes is perfect for a hot summer evening. (If the price of a cocktail here is beyond your travel budget, reserve a spot at Le Quarante Trois cocktail bar, a more affordable rooftop garden option atop the Holiday Inn Paris–Notre Dame.)

Among the 20 percent of Aruba that’s protected land, Arikok National Park boasts lava fields, limestone terrain, and a small beach, all crisscrossed with picturesque hiking trails. Paths lead to gold mine ruins, former plantations, and paintings by the island’s native Arawak people, making for an exciting place to visit. Explore the park by mountain bike, horseback, or car, or take a free walking tour with a park ranger (reservations must be made at least 24 hours in advance). You’re likely to see snakes, owls, bats, lizards, and myriad birds, as well as goats and the local donkeys.

After years at Ladera’s Dasheene Restaurant, where he won awards and was recognized as a leader of the island’s sustainable food movement, chef Orlando Satchell opened his own smaller restaurant on the coast. Presentation and flavor inform Satchell’s culinary creations, including his versions of island pepper pot and creole kingfish. Innovative salads like saltfish with christophene and papaya provide lighter options. Dinners are fixed four- to five-course menus, and lunches are available as well. Orlando’s is a welcome addition to the ever-evolving St. Lucian gourmet dining scene.

Set right on a stretch of sand, Eladio’s is a superb choice for a cool drink and a bite to eat while exploring the port town of Progreso. Dine in the large restaurant under palapa roofs or sit directly on the beach. Eladio’s has been a Yucatán favorite for over 60 years; the first outpost opened in Mérida in 1952. The coconut shrimp and fish in avocado sauce are great options for daytime dining, and the margaritas are refreshing in Progreso’s heat. Look for live music, day and night, which brings in the crowds.