Upper East Side

Although a glance up and down the manicured grass meridian of Park Avenue may conjure scenes from Bonfire of the Vanities or Gossip Girl, there are more than palatial apartments, elite private schools, and highfalutin clubs up here—starting with fantastic museums. The Metropolitan Museum of Art, the Solomon R. Guggenheim Museum, the Whitney Museum, and many others lie on and around "Museum Mile," as do a number of worthy art galleries. For a local taste of the luxe life, hit up the platinum-card corridor that is Madison Avenue for its lavish boutiques—between East 60th and East 82nd Street is like stepping into the pages of a glossy magazine and many fashion houses have their flagships here and showcase their lush threads in equally exquisite settings. Compared with the megastores of Midtown, Madison Avenue feels quieter; it's significantly less crowded and more conducive to leisurely shopping (window or otherwise). Beyond clothing, the boutiques here carry baubles to satisfy anyone's champagne wishes, whether it's a box of truffles at La Maison du Chocolat or an intriguing read at Crawford Doyle Booksellers.

Venture east of Lexington Avenue and you encounter a less wealthy—and more diverse—Upper East Side, one inhabited by couples seeking some of the last (relatively) affordable places to raise a family south of 100th Street, and recent college grads getting a foothold in the city (on weekend nights 2nd Avenue resembles a miles-long fraternity and sorority reunion). One neighborhood particularly worth exploring is northeast-lying Yorkville, especially between 78th and 86th streets east of 2nd Avenue. Once a remote hamlet with a large German population, its several remaining ethnic food shops, 19th-century row houses, and, one of the city's best-kept secrets, Carl Schurz Park, make for a good half-day's exploration, as does touring the most striking residence there, Gracie Mansion.

If art galleries are your thing, there are some classy places to visit on the Upper East Side. In keeping with the tony surroundings, the emphasis here is on works by established masters rather than up-and-coming (or even still-living) artists. Their locations are eminent as well: large town houses and upper stories in and around Madison and 5th avenues. Note that galleries often have limited hours, so make sure to check times in advance.