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A short drive north of the South Island town of Oamaru, Riverstone Kitchen is often lauded as one of New Zealand’s best regional restaurants. The stylish dining room is anchored by a robust fireplace crafted from local river stones, and much of the seasonal menu is crafted from the restaurant’s own organic orchards and gardens. A more relaxed café ambience for daily breakfast and lunches segues to a more formal mood at dinner from Thursdays to Saturdays, and the savvy drink list includes wines from the nearby Waitaki Valley as well as small-batch beers from around New Zealand. Ask if any of the excellent Belgian-style farmhouse ales from Oamaru’s Craftwork Brewery are available.

Southwest of Anguilla is one of the island’s top three beach areas: the two-mile-long brilliantly white stretch at Rendezvous Bay. Its long shore, steady breeze, and calm Caribbean waters provide a break from the crowds at Shoal Bay and Sandy Ground. The western end does offer some fun daytime beach-bar action, which grows rowdier at night and on the weekends, when the famous Bankie Banx’s Dune Preserve venue attracts residents and visitors for live music. You can view St. Martin, across the channel, from shore.

The colonial town of St. Pierre, on Martinique’s west coast, has a colorful past. Rich from the earnings of the sugar and rum trades, it was once considered the Paris of the Caribbean—until 1902, when it was destroyed by the violent eruption of the island’s largest volcano, Mount Pelée. A volcano museum in St. Pierre displays items plucked from the rubble and historic photos of the town before and immediately after the eruption. Today, the fine church with historic displays bears testament to the town’s comeback.

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.

Sailing is Anguilla’s national sport, but it’s also the best way to explore the island’s dreamy Caribbean shores—and the best way to explore its marine life while in transit. Spend the day with Tradition Sailing Charters, gliding across iridescent blue waters on a 1978 50-foot sloop, drifting from one cay to another. You’re welcome to watch and learn how to sail if you’re a newbie, or to participate if you have experience. After a lunch stop at the only restaurant in Prickly Pear Cays, get underwater to check out this reef-protected bay where sea turtles, blue tang, and numerous other tropical critters thrive. There’s also a brown booby colony on land here.

Perched high above the sea on the east coast of St. Kitts is Brimstone Hill, a massive stone fortress built by African slaves for the British during the 17th and 18th centuries. Now a UNESCO World Heritage Site, the military stronghold, which took 100 years to complete, is considered one of the best-preserved fortifications in the region. From the top, you can see six neighboring islands on a clear day.

You’ve likely seen the main attraction of Tulum in a travel ad, a postcard, or a friend’s Instagram feed, but there’s still nothing like witnessing first hand the only Maya site that overlooks the Caribbean Sea. Standing before the 13th-century structures will leave you feeling awed by the Maya’s archaeological achievement and its resilience—still standing after being hundreds of years of being buffeted by salty water and wind. True, it’s the main attraction here, but it’s not the only one. With a quirky backstory and a lot of international press, more and more foodies are making their way to Hartwood, a restaurant that lacks electricity. The chef prepares all dishes—made with local ingredients—on an open fire.

A Carioca version of the São Paulo classic, the Rio Astor has two straightaway advantages: It sits on a magical city corner, at the start of Ipanema, just across from the beach, and it has a wide, airy terrace. From there, visitors delight in its drink menu (one of the city’s most complete) as waiters scurry hither and yon at cocktail hour, serving draft beers, which are called chopps and which somehow taste creamier here. The Astor also features a wide-ranging menu that updates Brazilian classics with unusual ingredients and more ambitious presentations of standards like arroz com feijão. The entire mix translates to one of Rio’s winningest combo of bar-rail and white tablecloth venue.

Begin your perfect beach day with a stop at this snackbar on Positano’s Spiaggia Grande for a sweet brioche and a cold cappuccino freddo. In the afternoon, come back for a scoop of gelato or a chocolate-dipped ice cream–bar snack. At the end of the day as the sun drops behind the mountain and the day-trippers leave, perch on one of the high stools at the cocktail bar and sip a cold gin and tonic or draft beer. The bar is attached to a formal restaurant that overlooks the beach.

Fusion, one of Playa del Carmen’s oldest and best-loved beach bars, has an indoor restaurant area, but it’s most famous for its outdoor lounge, right on the sand, under palm trees, and hard by the Caribbean. Fusion’s central location in the busiest part of the downtown area makes it ideal for enjoying a day under a palapa’s shade, or a night out on the town with live music and fire shows. The menu offers a variety of international cuisine, so you can find almost anything you’re craving, whether it’s tacos, Argentine empanadas, or classic pub grub à la burgers and wings.

In a city teeming with markets, this is one of the capital’s only true farmers’ markets. Everything is grown and produced within 100 yards of the city limits. It takes place at the corner of a park in the Roma neighborhood, and wooden benches are set up so that visitors can enjoy mushroom tamales, hippie-style tacos filled with cactus and wheat berry salad, and refreshing ices in flavors like cardamom or cucumber lime. Don’t miss the booth that sells one of my favorite mezcals. It’s made in the state of Guerrero, and at the market, vendors funnel the liquor from huge vats into beer bottles decorated with colored straw and papier mâché animals.

One of Caye Caulker’s best beach bars is also its friendliest. Set right on the Split—a narrow channel dividing the island’s north and south portions—Caye Caulker’s most social corner invites tourists and locals to gather for a swim off an extended dock, or to enjoy a cocktail and music. Lazy Lizard’s recently upgraded look includes a variety of umbrella-covered wooden picnic tables, seating under palapas, and a new beach extension with steps leading into the shallow sea areas for easy entry. On the menu, you’ll find typical bar bites: burgers, fish tacos, and full meals like a lobster plate. The bar holds occasional full-moon parties, live music, family-fun days, and beach volleyball tournaments.

The Harvest Table opened Harvest Inn in 2015, and it quickly became one of the go-to spots in St. Helena. One of the main reasons: unpretentious food at reasonable prices. The 110-seat restaurant has a large horseshoe-shaped bar that serves upscale pub food, California style. Burgers are thick and juicy, and the fish and chips are crispy and light. The rest of the dinner menu is filled with hearty fare such as braised short ribs and grilled pork chops. Since its debut, the restaurant has launched its own beer program and now bottles microbrews, too. If you go, be sure to scan the crowd around you. Harvest Table has become the backdrop for many a business deal, and you never know which winery owner might be sitting nearby.

On the corner of a rather scrofulous downtown block and across the street from the Ace Hotel’s event space, Wildfang is a self-described “home for badass women.” Whether it’s street style with a feminist message—even in Portland, it’s not every day that one finds a “Slay the Patriarchy” baseball cap—or high-fashion clothing that works on all sorts of body types, Wildfang packs it all in. For hangers-on who aren’t as interested in shopping or fashion, the bar inside the store provides liquid relief, including beers designed in collaboration with 10 Barrel that were created by women brewmasters.

Mary Ellen’s is known for its delicious grilled cheese sandwiches, which are made in nine gooey varieties and are accompanied to the table by a wide selection of dipping sauces. The menu makes a half-hearted (a little joke there) effort to promote healthy options like kale salad and avocado toast, but really it’s all about the bar food at this friendly neighborhood joint in Old Town. The game’s always on the television, and there’s a regular schedule of trivia contests, open-mic comedy nights, and beer-fueled spelling bees, all of which go well with grilled cheese.