Update from article originally published 24 February 2010.
There is no right way to see New York. Want to see the Statue of Liberty, Empire State Building, a Broadway play? Fine, so do many locals. But other things more easily separate visitors from New Yorkers.
Spend at least 20 seconds at South Street Seaport. This commercialized strip of shops and that confounded 'Bodies' exhibit has never seen a single New Yorker come without the company of out-of-town guests. Not one.
Walk around Times Square, a lot. Even hardened locals pause a second to admire the lights of Times Square on occasion. But few ever spend more than 10 minutes there, and zero would consider going more than once in a month, much less on a three-day weekend.
Be scared of East Village's St Marks Avenue. (errr...we meant 'Place'. Thanks to the sharp commenters!) And its punks, tattoo parlors, 'New York F***ing City' t-shirts, plus the Chipotle Mexican-food chain in the building where Andy Warhol once staged his wild 'Exploding Plastic Inevitable' events. It's not remotely dangerous. Just go, be a bit trepid, then brag about it afterwards.
Skip Brooklyn. This '90s throwback will separate you from being any local, who knows you get more space, less stress and pressure -- and frequently better-value meals -- at Brooklyn restaurants in Boerum Hill, Park Slope, Prospect Heights, Fort Greene, Ditmas Park or Williamsburg.
Take a double-decker bus tour. If you want to see New York by one, go ahead. But don't expect any street-cred points looking down from the open top. New Yorkers prefer buying an all-day subway/bus pass, getting a free bus map, and crisscrossing Manhattan on their own. It's much much cheaper ($8.25 vs $39) and you don't have to listen to the guide the whole way.
Order a 'piece of cheese pizza.' Locals call it a slice here. You can just say, 'gimme a slice, guy.' And you'll get that piece of cheese, nice and toasty.
Go to Wall Street or Midtown on weekends. It's deserted. Though busy, the areas are alive Monday to Friday.
Eat in Little Italy. And debate in whispers whether the waiter and people at next table are in the 'goodfellas.' (The diners are from Houston, though we're not so sure about the waiter...) As dining goes, Little Italy is wayyy past its prime. Go to Roberto's in the Belmont of The Bronx for the real(er) thing.
Point at the rats. They say there's always a rat within five feet of you at any time in New York. You're most likely to see them around garbage after dark or on the subway tracks any hours. Locals take it easy, and don't point or squeal. Unless the rat's on the subway platform. Then it's prison rules for all. (By the way, the exact same rule applies for celebrities.)
Exhibit any US geographical knowledge. Other than New York, New Jersey, Florida and California. Every other state should be confused for North Dakota. (Little known fact: New Yorkers have the world's worst sense of geography.)