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. It’s also a key destination for visitors, because some of the most fantastic museums in the country are here.
There's a reason this stretch of Manhattan is called "Museum Mile": this is where you'll find the Metropolitan Museum of Art, the Solomon R. Guggenheim Museum, the Cooper Hewitt, Smithsonian Design Museum, as well as a number of art galleries. For a local taste of the luxe life, catwalk down Madison Avenue for its lavish boutiques; strolling the platinum-card corridor between 60th and 82nd Street is like stepping into the pages of a glossy magazine. Many fashion houses have their flagships here and showcase their lush threads in exquisite settings.
Venture east of Lexington Avenue and encounter a less wealthy—and more diverse—Upper East Side, inhabited by couples seeking some of the last (relatively) affordable places to raise a family south of 100th Street, as well as 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 catching a glimpse of the most striking residence there, Gracie Mansion.
If art galleries appeal, there are some elegant ones on the Upper East Side. In keeping with the tony surroundings, the emphasis here is on works by established masters.