Upper East Side

To many New Yorkers, the Upper East Side connotes old money and high society. Alongside Central Park, between 5th and Lexington avenues, up to East 96th Street, the trappings of wealth are everywhere apparent: posh buildings, Madison Avenue's flagship boutiques, and doormen in braided livery.

While a glance up and down the manicured grass meridian of Park Avenue may conjure scenes from Bonfire of the Vanities or the TV series Gossip Girl, there are more than palatial apartments, elite private schools, and highfalutin clubs up here—starting with world-class museums. The Metropolitan Museum of Art, the Guggenheim, 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, marble-counter cafés, and the epitome of class, the Carlyle Hotel.

Venture east of Lexington Avenue and you encounter a more affordable—and more diverse—Upper East Side, one inhabited by couples seeking some of the last 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 remaining ethnic food shops, 19th-century row houses, and, one of our best-kept secrets, Carl Schurz Park, make for a good half-day's exploration.