The Upper East Side has a reputation for snobbishness, but in reality it's home to a surprisingly varied population; from the mink-coat-wearing old ladies and German or Hungarian immigrants in the 80's, through the Black and Latino population in southern Harlem. The area contains more millionaires than almost anywhere else on earth, but you can also find a good meal for , and endless free entertainment.
Museum Mile along Fifth Avenue has some of the world's best museums. Don't miss the Metropolitan (worth three days on its own) or the Guggenheim, but there are also dozens of smaller, less famous, fascinating places. Check out the Museum of the City of New York (local history), the Gagosian Gallery (contemporary art), the New York Academy of Medicine Library, and the Museo del Barrio. When the weather’s nice, enjoy the quiet in Central Park’s Conservatory Garden, or peoplewatch at Carl Schurz Park on the river. And don’t forget to eat—you could go to a different restaurant every night for a year if you wanted to.
Quick Tips:
Wear comfortable shoes! You'll be walking a lot. New Yorkers are stylish, but they do wear sneakers.
It gets cold in the winter. From December through February, lows around 20ºF (-6ºC) aren't unusual, so wrap up. Summers are hot but indoor spaces will always be air-conditioned, sometimes to sub-arctic temperatures, so bring a sweater.
New York is a very expensive town, but there's always someplace to get a cheap bite, and there are a lot of free forms of entertainment. Many museums (including the Met) have suggested donations instead of set entry fees. In the summer, there are a lot of free performances (theater, dance, opera, concerts, films) in the city's parks.
Best Way To Get Around:
The subway is great. The 4-5-6 line runs along the Upper East Side. The 4 and 5 trains run express, making infrequent stops. The 6 train is local, stopping every eight or nine blocks.
Coming from the West Side, the best thing to do is catch the bus, either the 86th Street or the 96th Street crosstown.
Subways and trains cost for a ride, with free transfers between the two within two hours. A 1-day unlimited ride Metrocard costs .
Taxis are fun but expensive: .50 when you climb in, plus .40 per 1/5 of a mile and a .50 surcharge at night.
Really, though, the most fun is to walk. No matter where you're going, walking in Manhattan is always exciting.