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West Randolph Street in Chicago’s West Loop has become a new home to the city’s culinary talents. Stephanie Izard first drew crowds cooking dishes like roasted pig face at Girl & the Goat (the restaurant pictured above). She then opened Little Goat, a retro diner, across the street. Graham Elliot Bowles keeps it simple at his casual g.e.b, where each dish has no more than three ingredients. On a more elegant note, the prix-fixe menu at Grace, from chef Curtis Duffy, features dishes such as kampachi with coconut, lime, basil, golden trout roe, and pomelo presented in a cylinder of frozen ginger water.

Mama Shelter’s owners, who launched the Flèche d’Or indie rock club across the street, turned an outlying location in the 20^th arrondissement into an advantage. They enlisted Philippe Starck to design the restaurant, bar, pizzeria, and summer rooftop terrace—which now attract poets, artists, and counterculture types from across the city. The hotel’s street cred is still intact years after the 2008 opening, and the decor—black ceilings turned into graffiti chalkboards bearing literary quotations; Mexican wrestling and Halloween masks turned into lamp shades; tree trunks used as stools—remains relentlessly hipster without being overwhelming; guests could be young parents with sleeve tattoos toting baby carriers in the elevators.

A five-level emporium specializing in French luxury brands (Louis Vuitton, Dior, Chanel), Le Bon Marché traces its origins to a stall run by a hatmaker’s son and his wife in 1852. The beauty department is under an Art Deco glass ceiling; the third floor features an extensive children’s department with toys, books and clothing. La Grande Épicerie de Paris, Le Bon Marché’s expansive and extraordinary food hall, is across the street.

Pier 1’s greatest appeal is its setting: The open-air restaurant and nightclub occupies a pier that extends out into the Caribbean in Montego Bay. By day and into the early evening, the restaurant draws visitors and locals interested in a good meal with a stellar water view. At night, regular parties start late and run into the wee hours of the morning. Skip the noisy chain restaurant-bars down the street and try something more Jamaican, instead.

Tucked away in the Kalorama neighborhood is an urban oasis of steps and terraces connecting S Street and Decatur Place NW. Designed in the early 20th century during D.C.'s “City Beautiful” movement, the Spanish Steps vaguely resemble the original version in Rome, but the smaller scale and residential surroundings create an intimate, sheltered feeling. Like Rome, D.C.'s Spanish Steps are a neighborhood landmark and a natural gathering place with a romantic touch.

Close to Miami’s busy center, but set back from it, the Mandarin Oriental, Miami enjoys a quiet spot and the designation of the only hotel to sit on Brickell Key, a small island connected to Brickell Avenue by a bridge. This location gives the Mandarin Oriental a sense of both exclusivity and privacy; it also means that rooms offer some pretty incredible views of Biscayne Bay, the city, and one of Miami’s causeways. And what rooms they are; with 13 different types, expect a variety of choices with respect to layout and amenities. Standard in every room, though, are oversized tubs, large flat-screen televisions, Illy espresso machines, luxurious linens, and Carthusia toiletries. Turndown service is also included, as is the guest’s choice of newspapers, delivered to the room each morning. Mandarin Oriental, Miami does not have beachfront access, but it does have a pool. Finally, although the hotel doesn’t go out of its way to advertise the freebie, Wi-Fi is complimentary for guests who set up an account on the hotel website.

Museum cafes are often depressing affairs, white formica boxes where you grab a curling sandwich on your way to the next piece of tourism. But the main cafe’s trio of rooms are nothing like that. Designed, respectively, by William Morris, Henry Cole, and Edward Poynter in glorious Victorian excess, were the first museum cafe in the world, and they are today a rare example of a museum restaurant where you would be happy to spend time, revelling in the gorgeous details and stained glass windows. And the food’s pretty good too; you can get all sorts of hot and cold meals, and it’s a great stop for lunch or cakes, if you’re doing the museum trail at South Kensington.

Just a few blocks from the bustle of Old Town and Duval Street, this Caribbean-style resort is a serene retreat with a swath of white-sand beach, a pool concierge, and a private pier for fishing or gazing out over clear turquoise waters. All of the contemporary rooms and suites are generously sized and have private balconies with views of the pool, courtyard, or ocean, but the real draw remains right outside your door. Guests can snorkel off the shore, face off on the giant chess board, or simply sway between two palms in one of the beachside hammocks. They also have privileges at sister resort Casa Marina, just up the beach, including at the oceanfront Spa al Mare. Have kids in tow? The hotel offers a full roster of activities, plus babysitting services for parents who want to hit the town.

The outdoor cantina upstairs at the famed Coyote Cafe makes a perfect spot to perch and enjoy a bird’s-eye view of the bustle of the Santa Fe streets. Try the Lava Lamp cocktail, a more-delicious-than-it-sounds blend of draft beer and a frozen margarita. Other concoctions like the prickly pear margarita make excellent companions to the warm, thickly cut tortilla chips and fire-roasted salsa.

In 2001, hotelier Ian Schrager tapped French designer Philippe Starck to reconceptualize The Clift Royal Sonesta Hotel’s wildly modern interiors. A complete contrast to the building’s historic facade, the lobby is dark, edgy and filled with a quirky smattering of cool furniture—among them chairs by Ray and Charles Eames, a coffee table by Salvador Dali, and a surreal stool by Renee Marguerite. Upstairs, splashes of lavender brighten more neutral rooms, which feature wheelbarrow-shaped chairs and sleigh beds designed by Starck. Merino wool blankets are primed to battle foggy nights, while MALIN+GOETZ bath products soothe well-traveled skin with natural ingredients and science. Downstairs in the Redwood Room, a see-and-be-seen crowd nurses drinks. The swanky lounge sports sleek backlit shelves, its original redwood paneling, and a bar supposedly crafted from a single redwood tree. Though The Clift sits just up the street from Union Square, it feels far away from the tourists.

La Casa de La Abuela is a Oaxaca mainstay, on the corner between the Zocalo and the Alameda, Oaxaca’s two central squares. Find the entrance on Hidalgo street, and climb the steps up to the second floor. As soon as you enter you’ll see a big clay comal and a woman making fresh tortillas, the sign that this is the real deal: authentic Oaxacan food. They serve local specialties including four kinds of mole (almendrado, coloradito, amarillo and mole negro). Choose a spot by the window to enjoy your meal while you watch the action in the square below.

The winding streets of ancient Genoa all lead in one direction—straight up. Lace up your tennis shoes and keep climbing. Eventually you will reach a small park at the edge of the city, the entrance to one of the many fortresses that speckled its 17th-century walls. From here you’ll be treated to one of the best views of both old and new Genoa. Come at dusk for a stunning sunset over the urban edge of the Ligurian Sea. (And if you are too tired to walk back down, catch the funicular for less than two euros!)

Port Royal, once known as the wickedest city on earth and the Sodom of the New World, revels in its pirate past. The once-great city, now a fishing port, was at its height in the 1600s, when numerous brothels and drinking establishments thrived on pirates’ plundered gold. In 1692, the effects of an earthquake submerged part of the port, a tragedy that has actually preserved the town from being torn down or built over. Entire buildings and streets are clearly visible just beneath the water. The town that remains on dry land offers visitors fascinating archaeological sites to explore, including fortified walls, cannons, and crumbling buildings.

Apparently, you don’t need a rockin’ house or an haute hotel to throw a massive pool party. The only thing missing from the poolside shindigs at these downtown Scottsdale bars are the floaties. First, there’s Spanish Fly Mexican Beach Club with its private cabanas and day beds. Then just down the street is Maya Day and Nightclub, which not only has private plunge pools but also a taco bar, LED video screen and floating stage that hosts DJs and live music. Rounding out the trio is El Santo, a cantina and patio bar with a 15,000-square-foot Mexican resort-style pool.

Located one street back from the tram line in Sultanahmet, Tribal Art Home’s owner Nihat and his assistant Yekta will help you browse their extensive range of hand-crafted ceramics, mosaic lanterns, candle holders, waterpipes (nargile), and textiles—wall hangings, cushion covers, and handbags. The bargaining is minimal as the prices quoted are already reasonable. The guys here can pack and wrap your purchases for safe transportation home. If you’re concerned about the weight of your suitcase, door to door delivery via international post can be organized. Do know that parcel post from Turkey can be expensive, so check the prices by weight before committing.