Issue 7: New York

Remember to visit Manhattan classics in addition to trendy hotspots. Keens Steakhouse, founded in 1885, fits the bill, delivering Old New York in spades—gloriously juicy steaks, fat mutton chops and oodles of atmosphere. Ask for a table where you can see the huge painting of the tiger, or have a fabulous lunch at the bar while “Miss Keen,” a painted nude, gazes down at you languorously from her perch above the fine Scotches. And don’t forget to look up! The ceilings here are lined with the smoking pipes of former patrons, including Babe Ruth and Albert Einstein, whose pipes are proudly displayed in the foyer.

Elegant and luxurious without being too old-fashioned, The Surrey is a smartly located hotel steps from Museum Mile, Central Park and all the glittery shops of 5th and Madison Avenues. With a rooftop garden that boasts one of the best views in town, modern design, attentive staffers and great food—Daniel Boulud’s Café Boulud is downstairs, and does room service—this is a fine choice for a splurge. Bonus: It’s dog-friendly.

Consummate New Yorker Robert De Niro owns this charming Tribeca gem. Neither showy nor noisy—hard to come by in a hotel here—it has tons of well-appointed rooms, some of which include big bathtubs for soaking in after a day roaming the city, or views of the sparkling Hudson River. The best part of the Greenwich is its in-house restaurant, Andrew Carmellini’s Locanda Verde, where you can expect incredible housemade pastas and the sweetest service. If you can’t secure a table at the popular spot, order Locanda room service or dine on the secret, leafy hotel patio.

Take advantage of New Yorkers’ good taste: Shop where they shop. The Brooklyn Flea is a roving market whose location changes by the day and the season (check its website), including an old, gorgeous bank building in downtown Brooklyn. The goods are almost always fantastic: Bentwood chairs; handmade prints by a local artist; stunning New York–made cutting boards for your kitchen. And don’t forget to try the food; from one of the city’s best lobster rolls to a famed porchetta sandwich, it’s tough to go wrong.

It’s a New York rule: You must eat pizza while you’re here. Locals will argue about the best in town—Di Fara in deep Brooklyn is great; Zero Otto Nove in the Bronx is solid; Grimaldi’s is a throwback. In Soho, conveniently enough, is Rubirosa, a fantastic pizzeria that is not only romantico, it also takes reservations in advance. Order thin-crust pies with spicy soppressata or sausage, a bottle of red wine, and a table tucked into a corner.

Sexy and fun, the Meatpacking District’s Gansevoort boasts a rooftop pool and bar, proximity to great shopping and restaurants, and breathtaking views. (Look for the Freedom Tower and the Empire State Building!) This is not the sort of place you’d put up your parents; rooms have bold color schemes like purple and white. Pro tip: Spring for a room with a sweet little Juliet balcony, all the better to enjoy the sights and sounds of NYC.

Ideal for those visiting to see shows on Broadway or do business, the Sanctuary manages to be modern and stylish without being overly trendy. The rooftop bar and restaurant, Haven, is tented and heated, so if you’re here in winter, you can still enjoy the vistas while sipping a hot toddy. Its location off Times Square means buzzy street-level noise, so request a room at a higher level; the solicitous staff tends to be very helpful on that front.

Hotel on Rivington represented a major shift in the Lower East Side when it opened in 2005. Its glass façade, ultramodern design aesthetic and chic bars and restaurants draw the young, chic set. Shopping in the neighborhood, whether at a little designer boutique or a vintage shop, is trendy and fabulous. Make time to visit Viktor and Spoils, the in-house Mexican restaurant and tequila bar. In addition to its interesting mescal and tequilas list, the churros—fried dough served with three types of dips including chocolate—are delicious.

A well-kept Chinatown secret, The Fat Radish is one of the best date spots around. It’s dimly lit, with an urban barnyard aesthetic including white-washed brick walls, lots of light and a chill vibe; Bob Dylan was playing the night we visited. Every meal starts with gratis pickled radishes, but the entrées are plenty substantial: celery root pot pie with Gruyere has a flaky crust, and a kale Caesar salad is strewn with bacon, anchovies and slices of soft-cooked egg