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Spectacular hilltop villages are a dime a dozen on the Greek islands, but Astypalea, a distant speck in the Dodecanese, has the quintessential sugar-cube capital cascading over a rocky outcrop to a sheltered harbor. The oldest houses are huddled along the cliffs circling the Venetian Querini Castle. Castro Bar is built right into the 15th-century castle walls (which look even more dramatic when illuminated by moonlight). A series of small terraces on different levels, painted in white, burgundy, and blue, all offer stupendous views across the island and what feels like the whole Aegean. The vibe is mellow, and the drinks are strong. Stay until the sun rises out of the sea, a trippy experience you won’t forget.

Dumplings are a northern Chinese staple—inexpensive, hearty, and with a variety of fillings—and the boiled dumplings (shuijiao) at Baoyuan don’t disappoint. What sets them apart from your corner dumpling shop is the colored dumpling skins, dyed with juice from spinach, tomatoes, carrots, and purple cabbage. Customize your order by choosing your skin and filling—say, a spinach dumpling filled with cucumber, cilantro, pork, and lotus root, or a cabbage-dyed purple wrapper with bean sprouts, crispy rice, pork, and cabbage inside. There’s no denying that these dumplings photograph well, and that, plus the quirky venue—two dining rooms reached by a stroll through a fake garden and over a bridge—makes this a worthy place for a cheap and cheerful lunch or dinner.

Witness the destruction wrought by Mt. Vesuvius nearly 2,000 year ago at the archaeological site of Pompeii. The ancient village was frozen in time beneath a blanket of hot ash during an eruption in 79 C.E. Among the ruins that have been uncovered are buildings that shed light on aspects of ancient life both grand and mundane, from the temples, the coliseum and homes with fine frescoes, to public baths, chariot-rutted streets and grain stores which now hold plaster casts of the people who perished that fateful day.

Guests often describe their stay at The Beresheet as “otherworldly,” most likely because of the property’s unique setting atop a cliff that slopes into the 120-million-year-old Ramon Crater. The 111-room hotel spreads out over two floors—guests in ground-level villas cool off in infinity plunge pools, while those on the second floor watch sunsets and shooting stars from their balconies. There are also indoor and outdoor pools overlooking the Ramon Crater as well as excursions to explore the crater by bike or Jeep. Indiana Jones wannabes can even arrange to rappel down into the crevasse.

Located in the middle of New York harbor, less than half a mile from Manhattan (and even closer to Brooklyn), 172-acre Governors Island feels like a world unto itself, far from the bustling city. It has played a key role in the defense of New York at various points and two fortifications here, Fort Jay and Castle Williams, reflect that history. From 1966 to 1996, the island was a Coast Guard station; since it closed, the city, state, and federal governments have discussed various plans for the island’s development. In the meantime, it is open to the public for six months each year, from May 1 to October 31, when it is possible to wander among the Coast Guard barracks, visit the commander’s house, and bike around the mostly car-free island. Ferries depart from both Manhattan and Brooklyn starting at 10 a.m. and running until 6:15 p.m. on weekdays and 7 p.m. on Saturday and Sunday. During many weekends in the summer, art fairs, food festivals, and other events help draw visitors to the island, but even if you go on a day without anything special scheduled, a journey here provides a refreshingly different perspective on New York.

Maputo’s heart is the Praça da Independência, or Independence Square, sitting amid a surprising blend of architectural styles and straddling the city’s uptown and its historic downtown area called Baixa. Renamed in 1975 after Mozambique won its independence from the Portuguese, the square is dominated by a large statue of the country’s first president, Samora Machel, who died in a mysterious plane crash. On the north side of the square, look for the neoclassical city hall. To its east, the Art Deco Cathedral of Our Lady of the Immaculate Conception, which resembles a wedding cake and was consecrated in 1944, is impossible to miss. Nearby, the French-Mozambican Cultural Center hosts everything from jazz performances to art exhibitions, and the Tunduru Botanical Gardens, a few blocks away, are worth visiting for some shade from the African sun.

The perfect place to shop for anything and everything from all the islands is the 155-year-old public market called Le Marché. Located two blocks from the waterfront in the heart of Papeete, the market covers two stories. The lower level is filled with hundreds of stands offering Tahitian-made crafts, oils, vanilla, fruits, and flowers. Upstairs is reserved for artisans selling pareos, carvings, Tifaifai wall hangings and quilts, embroidered cushion covers, and other handicrafts. You’ll also find a few good shops for purchasing unique black pearl jewelry at fair prices. An on-site cafeteria serves local dishes. Le Marché is not just a tourist attraction, however—it’s a proper market where locals come to shop for meat, fish, fresh flowers, and produce and to chat with friends over coffee at one of the patisseries.

The cobalt-blue-and-brick-red residence where now-legendary Mexican visual artist Frida Kahlo grew up—and at times lived with husband Diego Rivera—is one of the city’s most consistently packed attractions; buying tickets in advance is strongly recommended. That said, the visit is essentially (and justifiably) mandatory and offers fascinating glimpses into this extraordinary woman’s life and work. In addition to holding some of her paintings, the house also functions as a showcase for her library, astounding wardrobe, and collection of pre-Columbian artifacts; it additionally bears witness to her close association with left-wing politics. What’s more, the museum portrays the artist’s struggles with depression, marital infidelities, disability, and illness. The house’s garden—home to a modest café and mostly bashful felines—makes for a great breather before more strolling in the Coyoacán neighborhood.

Near the wharf along upper Bay Street, a distinctive, street-level arcade connects several historic stone buildings, which once functioned as arrowroot warehouses. For centuries, these rows of Georgian stone arches and second-floor overhangs have sheltered Kingstown’s workers, walkers, and vendors from the hot sun and occasional shower—hence Kingstown’s nickname, the “City of Arches.”

A mile-long strip of soft white sand frames Friendship Bay on Bequia’s southern coast. The water here is consistently calm, making it perfect for swimming and snorkeling. You’ll likely have much of the beach to yourself—except for, perhaps, the area in front of the Bequia Beach Hotel, which welcomes non-guests to its lively beach bar.

You’ll likely do your sunbathing and swimming on the white-sand beaches of the Grenadines, but St. Vincent’s black-sand beaches are also quite stunning. In Biabou, for example, along the windward coast south of Georgetown, you can stare for hours at frothy ocean waves crashing onto the volcanic black sand. With luck, you’ll also catch a rainbow.

Find everything from candles and straw hats to t-shirts and fine resort wear at Basil’s Bazaar, a tiny boutique adjacent to the famous bar itself. Most of the goods are branded with “Basil’s Mustique” in one way or another, so everyone is sure to know where you’ve been—but that’s the point, right?

Within shouting distance of Port Elizabeth on Bequia, Princess Margaret Beach features a broad strip of white sand framed by palm trees and seagrape plants. Get here by water taxi, car, or a fairly rough cliffside nature trail, then head to Jack’s Beach Bar for lunch, happy hour, or both.

One of the five small, uninhabited Tobago Cays in the southern Grenadines, Baradel is home to brilliant white-sand beaches that double as nesting grounds for green sea turtles. On the southeastern shore of the island, there’s even a turtle reserve area, where you can swim alongside the graceful giants in a crystal-clear lagoon.

Explore underwater arches, tunnels, and grottos at this north island dive site—one of Dominica’s most popular descents. Here, blackbar soldierfish and glasseye sweepers patrol a sweep of exceptionally healthy hard and soft corals. Make sure to look down, where a fumarole releases bubbles on the ocean floor. Suitable for all levels, Toucari Caves has a max depth of 38 feet.