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In 1911, American star jockey Tod Sloan took a bar in Manhattan, dismantled it, and shipped it to Paris. At the time, American tourists and members of the artistic and literary communities were beginning to visit the City of Light in ever-increasing numbers, and Sloan wanted to capitalize on his fame and make the place a spot where expats would feel at home. Over the years, Harry’s New York Bar has been frequented by a number of famous Americans and international celebrities, including Sinclair Lewis, Ernest Hemingway, Coco Chanel, Jack Dempsey, Rita Hayworth, Humphrey Bogart and the Duke of Windsor. Whether or not you have star status, you can still settle in on a stool with a drink and soak in the history.

Visitors seeking an immersive-history experience can get a chance to travel back in time and check out the homes, stories, and daily routines of early Philadelphians, from everyday citizens to the city’s better-known inhabitants from the past. Buildings along Elfreth’s Alley, the country’s oldest continually occupied residential street, reveal the lives of the city’s earliest residents. Most of the houses on the block are private homes, but houses numbered 124 and 126 have been preserved as a public museum. Guided tours begin in the Museum Shop (Number 124). Private tours of the Alley and Museum House are available all year round.

Any hotel in San Francisco that has been operating for more than a century certainly has some stories to tell, and the Westin St. Francis is no exception. From socialites to celebrities to politicians, it seems every bold-faced name has slept (or attended late-night soirees) in its Bliss and Faville–designed towers. Today, guests to this distinctive 1,195-room property still enjoy top-notch service with some thoroughly modern touches: The 1904 landmark building recently underwent a $45 million renovation by Dallas-based interior design firm Forest Perkins, inspired by San Francisco’s moniker as “The Paris of the West.” Guest rooms are painted in Parisian blue, goldenrod yellow, and peony pink, and feature original crystal chandeliers. Downstairs, travelers can marvel at the lobby’s master clock—the first example in the western United States—and study a collection of photographs by Ansel Adams depicting the hotel’s long-lost Patent Leather Bar. Pro tip: Let the hotel’s resident historian bend your ear during a historical tour.

Nestled among the boutiques and restaurants that line the city’s main shopping street, the historic Hotel Goldener Hirsch has all the hallmarks of a Tyrolean hunting lodge right in the heart of medieval Old Town, from vaulted ceilings and mounted antlers to staff dressed in lederhosen and dirndls. Vintage guest-room keys are embellished with stag silhouettes, and even the tableware and linens in the two restaurants (one a former blacksmith, the other a goldsmith) feature the signature leaping-deer motif. Both serve hearty local fare—stop in for schnitzels, beef goulash, and bratwurst with sauerkraut, then call it a night in one of 70 cozy guest rooms, which balance cheerful country textiles and antique furnishings with modern amenities like flat-screen TVs, minibars, and free Wi-Fi.

Philippe Starck’s design firm, Yoo, transformed an 1872 dowager hotel into the 63-room Hotel Sans Souci Wien. Expect oversize Starck and Arne Jacobsen furnishings, four-poster beds, parquet floors, pillows made with Fornasetti fabrics, and pieces from the owner’s art collection (Picassos among them) that contrast with a soft color scheme. Downstairs in the spa, you’ll find a true Viennese rarity: a 65-foot indoor pool.

I stumbled along this place on a recent trip completely by accident. We’d been driving aimlessly for a while west of Kardemena looking for the perfect quiet beach to take in the late afternoon when I spied a few umbrellas through the trees between the road and the shore. I was pretty much equidistant between town and some of the huge resorts further to the west, so I figured I’d found my spot! I pulled off the road, unpacked all my stuff, marched through the trees to the beach and was met with a decent little beach, a small bar, those umbrellas I’d spied from the road and a small collection of older couples... Completely nude older couples. I wasn’t expecting this, but hey, I had no interest in spinning on my heal and re-packing up the car, so I assumed the proper attire (none), spread a towel out on a beach chair and settled in. I’m a go-with-the-flow kind of guy, after all. The beach itself is a mix of sand, pebbles and some larger rocks. The water is immaculately clear. And, as it turns out, the whole spot is watched over by one person Mandy — perhaps the nicest British lady on Kos who greets beach goers with an inviting smile and incredibly pleasant accent. I may not have been looking to take it all off, but knocking back a few Mythos beers with Mandy made for a pleasant end to the day.

Viñedos San Lucas is a new multi-use development fifteen minutes outside downtown. Its gracious, yet rustic hacienda vibe is attracting new neighbors plus locals and visitors to a complex that includes a quaint hotel and spa, two Mediterranean restaurants, one of the region’s finest wine cellars and even a polo ground. Vineyard excursions (don’t miss the lavender and olive groves) offer a glimpse of a Mexico few know; the mood is divinely bucolic. Time flies painlessly over wine and conversation, both outdoors and in.

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.

A city as ancient as Istanbul has many layers of history, and you’ll have to go below the surface to see the Basilica Cistern, the largest of the underground cisterns. Built in the sixth century for the Byzantine emperor Justinian, the atmospheric reservoir is supported by 336 columns, many of which have been repurposed from other ruins over the centuries. The Medusa-head column bases are a favorite to photograph, along with the carp that swim silently in the dimly lit waters. The cistern is located between the Blue Mosque and Hagia Sophia, and the best time to visit is simply whenever the line looks short, especially on a hot summer day—it’s always cooler underground.

The main church of Bologna, San Petronio Basilica dominates the main plaza. Construction on the church began in the 14th century and was dedicated to a 5th century Bolognese saint. One of the most fascinating parts of the church is the elaborate sundial found inside. The sundial is in the form of a meridian line and was added in the 17th century. The famous astronomer Giovanni Domenico Cassini designed the sundial and its measurements are amazingly precise.

Make your way to Market Street and head to the Hearst Building, where downstairs you’ll find Local Edition. This cocktail bar takes its inspiration from the thriving San Francisco newspaper business of the 50s and 60s, and it shows—you’ll sip on drinks while surrounded by vintage paper presses and archival newspaper clippings. Try their updated version of a San Francisco favorite, the Bloody Mary. Local Edition is open Mondays through Fridays from 5 p.m. to 2 a.m. and Saturdays from 7 p.m. to 2 a.m.

Soccer–or fútbol–has always been popular in Mexico, of course, but street soccer–games for homeless and at-risk players– is a slightly newer concept. With Mexico City having hosted the 2012 Homeless World Cup, however, street soccer gained both visibility and popularity in the Mexican capital. In season, you can see tourneys and other exhibition events in Mexico City. Consult the local street soccer website for the current calendar of games and their respective locations.

We become so small when entering a place of worship, this local woman especially as she made her way to the entrance of the Cathedral of San Gervasio in Valladolid. It wasn’t Sunday. I’m sure of it because Sundays in Mexican city centers are usually much busier with families wandering around the city and going to mass. On this particular day there were just a few folks going about their usual routine.

Cafe Sevilla is located in the downtown Gaslamp district in San Diego. It’s a great place to hear live music while sharing tapas and drinks with friends. The interior is huge with flags hanging from a 20ft ceiling, a bull on the wall behind the bar, and other Spanish-inspired decor. The owners are from Spain, and this restaurant has been here in San Diego for over 20 years. On weekends, it’s a good idea to make reservations for dinner since it does fill up quickly. There’s a little stage that is always occupied by flamenco, rumba and/or Spanish guitarists. If you want a little more quiet, ask for a table on the second floor—you can still hear the live flamenco, but it feels a little more private. Or, you can sit outside on the patio for people watching. 5th Ave in San Diego is a hopping little place, and Cafe Sevilla is a great start to your evening.

Concalma is the store of designer Matilsha Marxuach, a graduate of the Rhode Island School of Design who creates fair-trade products that are made and sourced locally. Her specialty is chic cloth bags and totes for men and women, and her trendy line offers a variety of sizes, styles and designs. Clothing, bags and jewelry by other designers, both quirky and cutting-edge, are sold here as well.