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There’s no better place in Hobart for a sundowner than this bar and restaurant, situated on the pier where the ferry to the Museum of Old and New Art departs. Its menu is filled with Asian-inflected dishes such as Korean fried chicken and pork belly bao.

The Hole is a geologic formation that offers a dramatic look at the same karst process that created Conch Bar Caves and other limestone sinkholes and caverns found throughout the Turks and Caicos Islands. As its name implies, the Hole is area’s largest limestone sinkhole, about 60 feet deep and 50 feet across. A pool of water at the bottom connects to Juba Sound’s nearby ponds through an underground tunnel. You can rent a car and drive to the Hole on the east side of Juba Sound; however, use caution when walking near the edge, as limestone can crumble.

St. Kitts’ water taxis—basically anyone with a boat willing to make the crossing to Nevis—will drop you right on this beautiful stretch of sand, making Oualie Beach the perfect day trip. Once on land, head to the Oualie Beach Resort, where you can hang with guests and locals at the on-site restaurant and bar. If you’re feeling adventurous, ask the bartender for a sample of one of the house-infused rums, made with a variety of local plants and herbs. Afterward, walk down to the beach, where you’ll find watersport vendors and even a small spa for some additional relaxation.

Gold Leaf cofounder Sonya Kemp worked at design collective SoLo in Solana Beach before fulfilling her lifelong dream of opening her own boutique. Now, she stocks her store with everything from kitchen utensils to kids’ toys, drawing inspiration from Zakka (a Japanese and Scandinavian movement that elevates everyday items). Shop for handblown glass lamps from France, midcentury modern furniture from Tijuana, and vintage clutches and jewelry. Then head next door to the Rose, the boutique’s neighbor here in the Historical 30th & Fern commercial center, for a glass of wine.

Parque de los Novios, in the center of Santa Marta’s colonial sector, is perfect for people-watching in the late afternoons when the tropical heat abates. Everyone from the gentry to the common folk—not to mention a plethora of brides posing beneath the gazebo—seems to treat themselves to a nice stroll around the park. Nearby restaurants and bars come alive after night falls, as do, of course, street artists and musicians.

One of the most popular anchorages in the BVI, Cane Garden Bay is home to a lively boating community. It makes a great day trip, whether you arrive by land or by sea. In this scenic cove, calm blue water laps a gentle arc of blinding white sand. Open-air beach bars offer lounge chairs and rum drinks; a few shops sell souvenirs, along with provisions for the sailors coming in off their boats to stock up.

The supper club is reinvented for the next generation at Yvonne’s, banishing any possible ghosts from the former Locke-Ober’s, and leaving just enough of the old girl (the beautiful hand-carved original bar and woodwork) to recognize her former self. The entrance is a bit mysterious, and the outer-bar area a happening scene. Walk through the “library,” a cozy space that looks like it’s right out of an Anthropologie catalog, and you’ll find lime-green banquettes, fancy chandeliers, and a modern web of lighting. The small plates are meant for sharing and make it possible to taste a good many flavors from the kitchen. Baked oysters Savannah are a nod to the well-heeled crowd, combining lobster, porcini cream, and Parmesan into a decadently rich mouthful. Seared halloumi has just the right sweet-and-savory combination and is a favorite that doesn’t disappoint. Be sure to make a reservation; there is usually a line. Try one of their crowd-pleasing punch bowls presented in unusual vessels. The “Goodbye, Me"—with Moroccan-mint-infused gin, sake, watermelon, lemon, and champagne—lives up to its name.

Consistently ranked among the world’s top beaches, and easily among the most popular and visited ones in Anguilla, the white and light pink sands of Shoal Bay host a casual and social atmosphere, with a plethora of bars and eats. The bright turquoise water is what Anguillan dreams are made of; water-sports options abound, from snorkeling right off the beach to parasailing and diving. Weekends get busy, with families flocking here and music echoing along the strand, especially from Gwen’s Reggae Grill. But if you just want to rent a chair and relax for the day, you can normally find a spot of Shoal Bay to call your own.

You know when the elegant maître d’ greets you at the door like a VIP—even if you’re not—that you’re in a first-rate Italian restaurant. Owned and operated by Italians, Otto is located in a restored heritage building, and its decor is a fusion of black glass, polished metal, and oak. The service is excellent (not always a given in Singapore) and the wine list is, too; but you’ll remember the food most of all. The mushroom-and-rosemary risotto is delicious, and so is the homemade walnut-and-ricotta tortelli with spinach velouté sauce. Savor the crispy suckling pig lacquered with honey, or the Hokkaido scallops carpaccio. Whatever your main dishes, dessert is a must. And not just the tiramisu and crème brûlée; the warm chocolate cake with Haitian vanilla ice cream and the mango-and-passion-fruit millefoglie with peach coulis are divine.

Bloody Mary’s, entertaining tourists since it opened in 1979, is one of those Bora Bora experiences that simply must be done. The ambience is beach-bar hip, with sand floors, colored lights, and coconut stools in a dining room under a thatched roof and surrounded by tropical foliage. Even if you don’t eat here, at least come for a cocktail to experience the vibe and mingle with the crowd of local pension, or guesthouse, owners, visiting celebrities, and other travelers. The food’s quite good, too: Fresh fish, seafood, and meats are grilled, American-barbecue style, with tasty results.

Zum Schwarzen Kameel’s unusual moniker, which means At the Black Camel, grabs your attention. It’s a play on the name of founder Johan Baptist Cameel, who opened the establishment back in 1618. Appointed a spice purveyor to the Hapsburg court in 1825, Zum Schwarzen Kameel is today a restaurant, with a separate delicatessen that makes good sandwiches and a gourmet shop selling fine cheeses and wines. The Kameel interior is justly famous as well, with a wood-paneled art nouveau dining room that (of course) postdates the era when Beethoven frequented the restaurant. The area around its Bognergasse location is now a stone-paved pedestrian zone with luxury shops, which makes the Kameel’s front terrace a delightful place to stop for a drink or meal.

When you’re looking for a fun night out, why not opt for one right on the Danube? The chic Motto am Fluss restaurant is located within the terminal for the Danube Canal ferries, but it’s like no dock you’ve ever seen before. The futuristic and super-bright space looks like a sleek cruise ship itself. On the lower level, the restaurant, with its black-and-white-checkered floor and silver orb lamps, reflects Venetian influences. Here, you can linger over breakfast in the café until 4 p.m. In warmer months when the weather is good, the terrace is the place for cocktails or biodynamic Austrian wines. On weekends, DJs add to the already-high cool factor in the trendy riverside spot.

Tapas and paella are the big draws at Zuzu, a tiny Spanish-inspired restaurant in downtown Napa. Small-plate portions range in price from $6 to about $15, and feature a variety of local produce—some from Zuzu’s own garden. Fan-favorite tapas include pan-fried Manchego cheese with roasted poblano peppers, Monterey squid and morcilla sausage a la plancha, and bacalao, dried salt cod drizzled with white truffle oil. Paellas are larger, more expensive, and more involved; most take at least 20 minutes to prepare. Choose between the paella of the day with chorizo, shellfish, and sofrito, and the black paella with clams, shrimp, mussels, and calamari. Zuzu also offers an interesting wine and beer list, with a number of imports from Spain. The restaurant doesn’t take reservations, so be sure to go early.

If you visit in the autumn, watch out for the falling apples on the outdoor terrace of this old fondue chalet in the center of the medieval village of Gruyères. Salads are fresh heaps of greens, bouillon is served with or without egg, and platters of AOP-protected (Appellation d’Origine Protégée, or Protected Designation of Origin) dried meats arrive on cutting boards. But since Gruyères is home to Switzerland’s first luxury product, Gruyère cheese, opt for heavy stuff like croûte au fromage (an open-faced grilled-cheese sandwich), gooey raclette served with boiled potatoes, Alpine macaroni and cheese, quiche gruyèrien, and moitié-moitié fondue, made with pungent vacherin and Gruyère cheeses and best washed down with Swiss wines like chasselas. In the winter, don’t miss the fondue vacherin, served melted in its original tree-bark packaging, or the chestnut vermicelles atop a bed of meringue and Gruyère double crème.

After a period of tribal skirmishes, the Fijians suddenly looked up and found they’d been colonized by the British. The Grand Pacific Hotel, built in 1914, shows just what fun it was to be British back then. Built along the same design as a ship—with promenades and prominent views—the Grand Pacific provides an interesting contrast to Waikiki’s old hotels, which all face inland. You can’t tour the Grand Pacific, but it’s worth a walk by or a drink at the bar.