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Colombian fashion designer Silvia Tcherassi took the design world by storm when she transformed a 250-year-old mansion in the center of Old Town Cartagena into a contemporary refuge that honors both past and present. Mansion Tcherassi’s seven rooms blend fashion-forward decor (think sparkly gold throw blankets) and original features such as restored stone walls and private balconies, but the vibe is much more understated, with ethereal fabrics, soft colors, and natural wood, in the 42 neutral-hued rooms at sister property Tcherassi Hotel & Spa. You can order fresh-caught seafood and icy raspaos (traditional drinks made with fruit and condensed milk) at the restaurant, while carpaccios, pizzas, and ceviches are on the menu on the rooftop lounge; the Italian restaurant at the mansion extends to a cozy patio facing a plunge pool and vertical garden made with thousands of local plants. After a day spent exploring Old Town’s historic buildings, relax with a Chinese medicine–inspired treatment in the spa, or take a dip in one of the property’s four pools.

Cesare al Casaletto is far off the well-beaten tourist track, but it is easy to get to: just take the 8 tram from Piazza Venezia or Largo Argentina and get off at the very last stop. Fifty yards from the tram tracks sits Rome‘s best trattoria, where spectacular fried appetizers (get them all, or at least the gnocchi fritti and polpette di bollito) give way to classic pasta dishes like carbonara and gricia. The second courses are excellent and fall-off-the-tailbone braised oxtail is a favorite. Pair it all with fairly priced natural wines from all over Italy and be sure to leave room for dessert, preferably the panna cotta.

Design junkies will find plenty to love at The Cape on Monuments Beach. Designed by Mexican architect Javier Sánchez, the hotel eschews resort staples like wicker and rattan for a sleeker look that marries mid-century standards with locally sourced furnishings and art. In the 161 spacious guest rooms, leather headboards and copper-leafed tubs complement private tiled balconies with ocean views. The style extends to the public spaces, which include Manta (acclaimed Mexican chef Enrique Olvera’s globally inspired seafood restaurant), a saltwater pool, and a spa that’s cleverly tucked into a natural rock formation.

About a two-and-a-half hour drive from Santiago (or 30 minutes by helicopter), Puma Lodge is located in the Andean foothills near the Argentine border. The lodge is part of the Chilean-owned Noi hotel group, which also has properties in Patagonia, Atacama, Santiago, and more. Opened in 2011, Puma Lodge has a ski chalet feel, with wooden interiors and a large fireplace in the middle of the bar and lounge area. The 24 rooms are all the same category, and the design is simple and comfortable with touches such as colorful throws and local artwork.

Many guests choose Puma Lodge for the heli-skiing, but there’s plenty on offer year-round and for the less intrepid traveler. Activities include hiking, horseback riding, or heading out for a picnic lunch by the river. There’s also an on-site spa, yoga studio, and wine cave. Outdoor hot tubs are great after skiing, and a swimming pool is a draw in the summer months.

Founded in the 9th century, Santa Maria della Scala was one of Europe’s first hospitals. It was also one of the first hospitals anywhere to disinfect its equipment and only stopped taking in patients in the 1980s. (The writer Italo Calvino died here in 1961.) The early history of the hospital is illustrated in the 15th-century frescoes decorating the walls of the Pilgrim’s Hall, and there is a fascinating archaeological museum housed in the labyrinthine basement rooms.

Beneath the path of planes taking off from LAX is an oceanfront runway for beginner hang gliders to get some air of their own. Sign up for a full (seven flights for $140) or half lesson (four flights for $85) with Windsports, which has been operating with A-class instructors since 1974. The experienced Greg DeWolf, whose longest flight clocked in at 6.5 hours, is a recommended guide. His passion, thoroughness, and humor are just what a novice needs to feel comfortable and confident piloting this new flying contraption. Relaxing is key, and once you do, the flights are a calming enjoyable ride. Just make sure to look up so you remember the experience!

In recent years, one restaurant has set the bar for cool in Cabo San Lucas. Bar Esquina, the Bahia Hotel & Beach House’s on-site bar and grill, features a chic casbah-like design aesthetic, a menu built on Mexican and Mediterranean flavors, and a commitment to organic, locally and responsibly sourced ingredients you taste in every bite. The menu is ever-evolving, but there are standouts you can always expect to find. The tuna tartare is a tiered, artistic creation, featuring tempura and an avocado-yuzu mousse. The Caesar is the signature Bar Esquina salad, here wrapped in a long, flat crouton and served with poached egg and prosciutto. Entrée selections include a generous filet mignon with potatoes au gratin and the short-rib pizza with blue cheese and arugula.

It was love at first sight. Everything about Orvieto is charming, with the exception of the Duomo (Cathedral) which more appropriately would be described as elegant and grand, especially the facade. Originally a thriving center of Etruscan civilization, Orvieto is a little less then half way between Rome and Florence. We had a lovely meal on one of the cute cobble stone lanes before heading up the clock tower and gazing over the perfectly preserved city. You could easily spend a day or two wandering through the town, enjoying its history and culture, both past and present. We were treated with the utmost hospitality at every turn. There weren’t many visitors during our visit, which I found to be unusual, given its popularity on the tourist circuit. This will be a place to revisit, and immerse ourselves into the everyday life of this gorgeous gem.

For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

The Hermosa Inn, first opened in 1936, has the kind of history that a cowboy keeps under his hat. With 43 rooms and casitas spread across six acres of Arizona desert in the upscale Phoenix suburb of Paradise Valley, the inn was originally the home and studio of cowboy artist Lon Megargee. A $5.5 million renovation completed in March 2017 updated the hotel for the modern era. It still retains a historic feel, but without the possibility of escape it had when Megargee, a welcoming host clearly uninterested in background checks, built a tunnel from the main building to the stable in case a visit by the sheriff made it necessary for less law-abiding guests to execute a quick getaway. But then, with Camelback Mountain as a backdrop, few guests nowadays are in a hurry to leave.

Mexico City’s fabulous Sundays-only flea market—in a down-at-the-heels neighborhood near the Centro Histórico that looks worse than it is—is a must-do for anyone who loves the nostalgic or the campy. No fewer than six block-long aisles host dozens of stalls featuring all manner of trash and treasure, including antique furniture and light fixtures; frilly housewares that get you back in touch with your inner grandmother; books and vinyl LPs (record players, too); artworks that might be worth a fortune; toys; dolls and action figures; and fantastic vintage beer and soft-drink trays that make great, practical CDMX souvenirs.

Few cuisines marry as well as Japanese and Mexican, a fusion that’s masterfully explored at Nick-San in Cabo San Lucas and San José del Cabo. Founding chefs Ángel Carabajal and Masayuri Niikura blend centuries-old Japanese recipes (including but not limited to sushi) with locally sourced ingredients to create exceptional bursts of flavor and a menu that has inspired additional locations around Mexico. The black and white tuna sashimi and tuna tostada are two of the most popular dishes, especially when paired with Nick-San’s own label of wines and sake. The original location is in downtown Cabo San Lucas, near the marina. A second Nick-San, in the Shoppes at Palmilla at the southern border of San José del Cabo, is a slightly more elegant space (gilding the lily, you might say) and includes a champagne bar.

Before Luis Barragán designed Mexico’s first master-planned community in the suburbs of Mexico City, he dreamed up an urban park neighborhood in his native Guadalajara. He commissioned German artist Matias Goeritz to create an entrance sculpture called El Pájaro Amarillo (The Yellow Bird) and drew plans for an onsite chapel named Templo el Calvario (Temple of Calgary). Unfortunately, the neighborhood today doesn’t look much like Barragán intended—he’d planned for a different kind of tree to be planted on each street so that the area would bloom in a rainbow pattern, and for wider streets lined with shopping malls. However, you can still visit Jardines del Bosque to see the majestic Goeritz sculpture and chapel and, if you squint your eyes, imagine Barragán’s vision come to life.

One of the joys of Rio’s southern districts—this in a city of mountains and hills—is their flat topography and network of bike paths, plus shared bicycles at stations all over the map. It’s as easy as downloading the Bike Rio app, grabbing one of the two-wheelers they call laranjinhas, and heading out to Lagoa Rodrigo de Freitas. Less than a half-mile from Ipanema beach, the lagoon is an idyllic postcard featuring the Tijuca jungles plus Corcovado in the background. All told, it’s five miles around, with views that change at every curve—and don’t forget the city’s spectacular sunsets.

We live in the age of artisanal everything, from chocolate and coffee, to, you guessed it, water. At Mexico City‘s Casa del Agua, staff produce and bottle “local water” on-site. The bottles—designed artisanally, of course—are charming souvenirs that you can use over and over again (with your own, less expensive water) once you’re home. Be sure to go to the second level of the shop to see the filtration process, and to the terrace level to see where the water is captured.