I was born and reared in NY. Here's my suggestions:
Someone earlier mentioned condition Orange. Good tip. Always be that way. Same for not looking up (too much.)
If your wife/girlfreind/S/O is going with you, tell her to only take purses with longer straps, and to wear them crosswise on herself (e.g. Purse on right side, strap over head on left shoulder.) Can't be snatched that way.
Avoid the subways later in the evening, especialy uptown (above 80th street.)
If a bum comes asking for money, a firm "no!" usually does the trick.
Safety in numbers. If you feel antsy, get to a group of people, or duck into a restaurant.
Finally, use common sense.
Now that that's out of the way, get a street vendor hotdog. Get pizza, there's none better.
FAO Schwartz. FAO Schwartz. FAO Schwartz. Everyone should see a toy store that sells actual full-size flying saucers for kids with waaaay too much money.
Empire State Building has the Twin Toweres whacked to the wide. There's a character about that building that the Trade Center can't touch.
Staten Island Ferry. Best public transportation ride in the world, and it's free. Just avoid the pretzels at the snack bar.
Guggenheim, MOMA, Museum of Natural History, Hayden Planetarium (I *think* they still do Laserium on the weekends.)
Mama Leone's. Great food, and the most amazing restaurant decor you'll ever see.
Bloomingdales. Everybody needs to buy just 1 thing from that place.
Tiffany's. Where else do you see 250,000 engagement rings like they're CZ fakes?
West Village. You can shop there till 5 in the morning. BUT: avoid the EAST Village at all costs.
Wall Street. Amazing how much money goes through that place every day.
Rockefeller Center. Go ice skating.
Probably the biggest disappointment will be Times Square. It's alot smaller than people think, and there's really nothing there.
Finally: A good gun shop, and just over the bridge in Jersey City is Jersey City Armory. Greg Monte always has great prices and a fabulous selection, and he's good people too. You can take the PATH (Port Authority Trans Hudson) trains over too.
PS: Find a Jewish Deli (Trust me: you'll know it when you see it) and have an Egg Cream. Trust me on this. It'll make your trip!
[This message has been edited by joegerardi (edited March 07, 2000).]