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Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)

Pisa’s famous leaning tower (the campanile of the adjacent Duomo) is part of the Piazza del Duomo, a UNESCO World Heritage Site that also includes the Duomo, baptistery and cemetery. Begun in 1173, the tower began to lean almost immediately thanks to soil subsidence. To try to halt the tilt, cables and counterweights have been inserted. A spiral staircase with nearly 300 steps leads to the top of this unique, iconic building.

San Juan Cemetery lies on the coast adjacent to El Morro (San Juan’s beloved fort) and nestled in the district La Perla, a rougher part of town. Its statues and tombs make it as beautiful as a New Orleans cemetery. Exiting El Morro, head down the grassy field to your left to catch this flustering overhead view. On this day, a powerful storm was rolling in, casting everything in gray.

The summit of Monte Solarno, the highest point in Capri is almost 2,000 feet high! You can choose to climb it or opt for the considerably easier chairlift. Along the ride and at the top, you will enjoy an incredible 360-degree view over the island and sea. There is a small café for a cold drink. Make the short hike down to the sweet, tiny 15th-century Hermitage of Cetrella, a chapel where local sailors used to visit and pray for protection before setting out to sea.

San Antonio’s west side is one of the city’s cultural hubs. Latin and Mexican-American influences are vibrantly displayed through public art and murals. The area around Guadalupe Street is an especially rich place to explore. You’ll find art around every corner, cultural centers, theaters, coffee shops, and bakeries. One of the best resources I came across was the San Antonio Neighborhood Tours sponsored by the City of San Antonio Office of Cultural Affairs. You can download free PDFs of the guides here: http://www.saculturaltours.com/. We did the West Side Murals Y Mas Tour. It was an awesome experience that included more than 50 unique sites.

Each Saturday from October to July (and once a month in August and September), the marina of Cabo San Lucas becomes a stage for local artists, musicians, and performers to peddle their wares and showcase their creative skills in the Circuito Cultural (Cultural Circuit), an event started by local entrepreneurs. Artists display their work from noon to 10 pm and live music and dance keep crowd entertained from 6 pm to 11 pm. The performances aren’t just Mexican in inspiration or origin; recent highlights even included Scottish country dancing.

Drink Kong is the neo-noir, Manga-meets-Blade Runner–inspired bar created by Rome’s Patrick Pistolesi. A labyrinth of dark-colored lounge spaces, with long bars, neon lights, and harlequin-patterned floors, Kong is both hang-out and experiment. Pistolesi, who has curated some of the city’s best bar menus and is one of the key players in Italy’s cocktail evolution, created an instinctive menu based only on flavors: bitter, sweet, dry. Either peruse the menu for a Kong signature cocktail like “Big Trouble in Oaxaca,” a spicy and slightly fruity tequila and mezcal drink or chat with Kong’s expert bartenders who can craft cocktails customized to your tastes. Or take a leap of faith in the Omakase Room, a Japanese-influenced wood-paneled room for private tastings in the omakase style—your drink will be whatever the bartender chooses for you.

The church of the mission of San Jose del Cabo is simple, both inside and out, but one of its charms is a special area where locals tie ribbons with petitions for divine intervention or expressions of thanks written on them. If you’d like to join in on the tradition and express your thanks, choose a white ribbon and write about what you’re grateful for on it. Then, tie it to the rack near St. Charbel Mahklouf, the somewhat obscure Lebanese saint who is believed to work miracles.

Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

Complete with an in-shop florist and white, honeycomb-tiled wall, this light-filled coffee shop is one of San Diego’s most Instagramworthy spaces. Luckily, it offers more than just good looks—the coffee comes from San Francisco’s Sightglass and the menu includes lavender-honey toast, chia pudding, and an assortment of croissants from Wayfarer Bread & Pastry. Owner Jen Byard is also the cofounder of San Diego’s popular Maker’s Arcade, a holiday market that takes place every December, so she has an eye for artisan items. Communal’s retail section is always stocked with tasteful finds like ceramic mugs and Mexican blankets.

In the mid-1800s, the Pioneer Mills family helped found San Antonio’s active flour milling industry. It’s fitting that their private residence, the Guenther House, is now home to a local history museum and a delicious restaurant that serves some of the best pancakes in San Antonio. The pioneer biscuits and waffles are also a favorite best enjoyed riverside. Come for the food, but linger for the history lesson.

At-home entertainers will enjoy the expansive digs at this Upper West Side property, where a number of studios and suites feature terraces and enough space to host upwards of 30 guests. Even its more modestly sized rooms evoke big-time comfort, though, thanks to luxury bedding, signature mattresses, and an array of everyday conveniences (think Keurig machines and free morning papers). There are plenty of perks to be found beyond the rooms as well, namely at the property’s three dining venues. Serafina restaurant excels at Northern Italian plates, while LOCL offers speakeasy-inspired cocktails alongside live piano sets and a library with an original fireplace. Guests will also want to check out RedFarm, where chef Joe Ng serves clever takes on Chinese fare and dim sum, such as oxtail dumplings and BBQ duck lettuce wraps.

Visiting Santiago Achaval and Manuel Ferrer’s boutique winery Achaval-Ferrer is a requisite visit while in Mendoza to sample Argentina’s most awarded wines. Their malbec wines and blends consistently earn high scores from Robert Parker, Wine Enthusiast and Wine Spectator. Started by a group of Argentine and Italian friends, Achaval-Ferrer’s Italian winemaker Roberto Cipressois specializes in small production wines that yield a high concentration of flavors, colors and aromas. Their beautiful 60-acre vineyard, Finca Bella Vista, offers free wine tours and tastings daily. You’ll sample three of their red wines, a sweet dessert wine and homemade olive oil. Chances are you won’t walk out empty handed. Calle Cobos 2601, Pedriel, Mendoza; +54 9 261 553 5565

The most famous café in town, this historic spot oozes period charm and maintains much of its original Belle Epoque decor. The main bar is for stand-up coffees and aperitivi, but there are several cozy salons for a sit-down treat. The terrace is a great place for people-watching.

Overlooking a postcard-perfect Venetian street (a former canal, now paved over) in the artistic Dorsoduro district, this 500-year-old merchant’s townhouse has been revamped as the boutique hotel Ca’Pisani. Behind the traditional exterior lies a modern den with clean lines and sharp, geometric forms that’s enhanced by original work from one of Italy’s most notable Futurist artists, Fortunato Depero. Architects Roberto Luigi Canovaro and Pierluigi Pescolderung balanced original design elements—exposed beam ceilings, brickwork—with 1930s touches, including one-of-a-kind inlay door designs and custom masonry and marble work.

Gaze out at the city’s rooftops from the hotel’s roof terrace, or mingle with locals over wine or an espresso at the street-level café. With the Peggy Guggenheim collection and the Gallerie dell’Accademia gallery just a stroll away, you’ll be able to journey from 16^th-century Venice to the 20^th century all in a few famous paintings.