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Dating to 1521, the Cathedral of San Juan Bautista isn’t just one of the oldest buildings in San Juan—it’s the second-oldest cathedral in all of the Americas. Go inside to see the tomb of Spanish explorer Ponce de León, who founded the first settlement on Puerto Rico and in 1509 was named the island’s first governor. The remains of St. Pio, a Roman martyr, can also be seen in the cathedral—the saint’s mummy has been displayed here in a glass box since 1862.

Pamela Echeverría founded her original Avenida Ámsterdam space in 2010, after experiences at Galería OMR and the Museo de Arte Carrillo Gil. Since then, the gallery has made a name for itself by providing a forum for contemporary-art proposals based on impassioned research; its catalog has included artists such as Teresa Margolles (2009 Venice Bienniale and the 2012 Prince Claus Award), Erick Beltrán, Santiago Sierra (2003 Venice Bienniale, representing Spain), and Héctor Zamora, as well as Jill Magid, Pablo Vargas Lugo, Terence Gower, and Antonio Vega Macotela. Labor’s current headquarters were originally functionalist architect Enrique del Moral’s 1948 residence and lie just across the street from 1980 Pritzker Prize winner Luis Barragán’s house, which was declared a UNESCO World Heritage site in 2004.

The famed German naturalist and explorer Alexander von Humboldt was the first to document the ocean current that explains why the adorable, nattily plumed penguins favor this part of the Chilean and Peruvian coasts—the water brings oodles of anchovies, sardines, and crustaceans along with it. (Both the current and the penguins were eventually named for Humboldt.) The reserve includes three islands—Damas, Choros, and Chañaral. From the boats bound for Punta de Choros, visitors can catch glimpses of dolphins, whales (including humpbacks and blue whales, especially in January and February), and frolicking sea lions.

As wine booms in Chile, Barrica 94 is the newest addition to the city’s wine bars. Located in the tourist-friendly Patio Bellavista in Bohemiam Bellavista, Barrica 94 is all about La Vid. Interior murals were designed by local painter and designer Tomás Ives and are contrasted by plush leather benches, and a wine list that will make grape lovers sing with delight. What to do here? Taste, taste, taste. The knowledgeable staff can help you and while wine is the star of the show, you can order some nibbles to complement them.

Just 14 kilometers (less than nine miles) from La Serena, the white-sand La Herradura Beach is ideal for swimming and relaxing, as the water is warm and nearly as placid as an outdoor pool. On-site lockers mean you don’t have to worry about keeping an eye on your stuff when you want to take a dip.

In 1989, Chilean winemakers Augustin and Valeria Huneeus happened upon a 280-acre parcel of land in the heart of Rutherford that had never been planted with vines. The couple jumped and bought it. The result is Quintessa, one of the most spectacular estates in the Napa Valley. Today there are three different ways to experience Quintessa—all visits are privately hosted and tailored specifically for each guest. The Estate Tasting includes a walk to a scenic viewpoint, followed by a seated sampling session in the main winery building. The “Quintessential Quintessa” includes a scenic drive to a private tasting pavilion atop Dragon’s Hill, which offers unrivaled vistas of the entire valley and revolves around narratives about the property, the terroir, and how winemaker Rebekah Wineburg plies her craft. Finally, the third—and most exclusive—option, dubbed the “Collectors Experience,” offers at least three wines from the Huneeus family cellar, poured alongside the most current release. Time the visit right and Augustin Huneeus himself might come out in his signature cowboy hat to say hello and regale your group with stories of his life in South America before he emigrated to the United States.

Opened by local restaurateur Lisa Wong in 1992, Rosario’s started as a neighborhood café, where San Antonio residents came to satisfy their Tex-Mex cravings. Today, it’s a city institution, known for its south-of-the-border specialties and house favorites. Don’t miss the tantalizing albondigas con arroz (Mexican meatballs braised in a spicy broth and served with rice and queso fresco), or the flavorful enchiladas Mexicanas (three queso-filled enchiladas smothered in a fragrant chile-infused sauce). And be sure to wash it all down with a perfectly crafted margarita.

The largely French-inspired menu at Republique has more than a few surprises on it, like the generous selection of oysters and kanpachi crudo in Thai green curry and peanuts. The high ceilings, walls of windows, and loads of natural light make the atmosphere ideal, as the omnipresent line outside suggests. The grilled octopus salad—made with cabbage, Santa Barbara pistachios, chile, citrus, and lime—is a must. Brunch, however, is the real draw. The brioche French toast is doused in Vermont maple syrup; pupusas come with Oaxacan cheese, avocado, a fried egg, and roasted poblano; and the kimchi fried rice is dished up with beef short ribs and eggs.

Hop on a lightweight bicycle and learn about the history of the Philippines on a guided bike tour around Manila’s old walled city of Intramuros. The bikes are handmade in the Philippines from bamboo, a natural vibration dampener, and fibers from the abaca plant (similar to a banana); Bambike Revolution Cycles won a Manila FAME Katha Award for Eco-Design in 2015. This is a unique alternative to a walking or bus tour, and takes you inside a walled city that is not normally accessible to bigger groups. Intramuros almost doesn’t feel like Manila: The Spanish influence is evident in the architecture, which includes some of the oldest baroque churches in the Philippines. Fort Santiago still houses underground dungeons as well as a tiny underground chapel, hidden at the end of a tunnel. At the Rizal Shrine you will learn about the life of José Rizal, the country’s national hero who played an instrumental role in the Philippine rebellion against Spanish colonial rule, and follow in the footsteps he made as he took his last walk in the fort from his cell to his execution.

Hidden Pond blends Maine cottage living with its own quirky, Instagram-worthy take on luxury. The enclave of 14 colorful one- and two-bedroom clapboard bungalows is spread over 60 acres of birch groves and balsam fir, just a 10-minute drive from downtown Kennebunkport. Each private house comes with a full kitchen that practically begs to be used, with first-rate cooking equipment and serving pieces and, for guests staying in the two-bedroom cottages, the option to send along a grocery list prior to arrival. However, dining at Hidden Pond’s farm-to-table Earth restaurant, with its awe-inspiring chandelier made from a preserved apple tree, shouldn’t be missed. For an even more memorable experience, guests can supper in one of two private garden sheds, which are outfitted with a sole table surrounded by hurricane lanterns, pitchforks, and potted plants, and situated steps from a chef’s garden that supplies ingredients for every meal. The Tree Spa is aptly named: Treatment rooms are nestled in the treetops eight feet above ground and are reached via wooden footbridges.

Lucerne is no stranger to mass tourism: The otherwise lovely medieval city swells each summer with list-checking visitors en route to central Switzerland’s famed Pilatus and Titlis mountains. Surprisingly, few of them make the 15-minute trek from the train station to this gorgeous 19th-century badi (open-air swimming area) on the Lucerne National Quay, overlooking the clear blue waters of what the locals call the Vierwaldstätter See (aka Lake Lucerne). The entire facility was meticulously restored in 2010 and remains a favorite of residents for its excellent views of brooding, multi-horned Mount Pilatus, Jean Nouvel’s lakeside KKL performance hall, and Santiago Calatrava’s Lucerne Station Hall—and all without the hassle of tourists.

At three times the size of the Big Island of Hawaii, this is South America’s largest island. Split almost equally between Argentina and Chile, Isla Grande de Tierra del Fuego is divided from the mainland by the legendary Strait of Magellan that saved sailors the long, treacherous route around Cape Horn. The Argentine town of Ushuaia, on the island’s southern coast, is a launching point for journeys that take travelers through the Strait of Magellan and past the glacier-covered 2,438-meter-high (7,999-foot-high) Mount Darwin off of the Beagle Channel.

Atop St. Paul’s Hill sit the ruins of St. Paul’s Church, built by the Portuguese and consecrated in 1521. Malaysia’s oldest church was first Roman Catholic, then Dutch Reformed and ultimately used by the British to store gunpowder. Missionary St. Francis Xavier was briefly interred here (after three weeks his remains were sent to Goa, in India, where they can be found to this day); an open grave marks the spot where he was buried. Adjacent to the church is the Porta de Santiago, all that’s left of the Portuguese fortress A Famosa; built in the early 16th century after the Portuguese took control of Malacca, the fortress was used by both the Dutch and the British.

If the city has you overwhelmed, whether by its chaos or its abundance of choices, and you want to take refuge in the familiarity of a hotel bar, you can’t do much better than St. Regis’s King Cole Bar. Sit inside at the bar or on one of its loungers and enjoy live music with your drink, or—better yet—head out to the terrace, where you can watch traffic zip by on the city’s main avenue, Paseo de la Reforma. You’ll also be looking out upon the Diana the Huntress fountain, a snapshot-worthy landmark in this city that has no shortage of them. In fact, you can also see the Angel of Independence statue and Chapultepec Castle from here. As for drinks, the must-try is the Sangrita Maria, a blend of mezcal, sangrita, and pasilla chile puree. Every St. Regis bar creates a signature cocktail, and this one is definitely representative of Mexico City. If you’re a smoker, ask to see the bar’s cigar selection.

English explorer and draftsman Frederick Catherwood and American adventurer John Lloyd Stephens were the first foreigners to rediscover Copán and numerous other Maya cities. Catherwood’s extraordinary lithographs, on view at the Catherwood House Museum, portray those monuments as they appeared when the pair first witnessed them; the institution’s Belle Époque setting transports visitors to Catherwood’s day and conjures the wonder he experienced as he wandered the Maya world of Mexico and Central America. A coffee enjoyed in the courtyard and a poke through the elegant gift shop are icing on the cake.