Sorry, I was on my way out and couldn't post legibly.
If you've never been to NYC, there are a few things that you really ought to do. You really should go up in the Empire State Building. Try to do that on a weekday morning if you can and you ought to beat some of the crowds. The ferry runs to the Statue of Liberty and I think it's free, but it's probably not worth it to spend 3+ hours waiting to walk up the stairs inside the statue. Just walk around, take some pictures and go back. The view of the skyline is spectacular.
To see a view that you can't get from the Empire State Building you can go to the observation deck on the Top of the Rock, at 30 Rockefeller Plaza. I think it's $15-$20 and you should buy your ticket in advance if you can plan for it.
Walk around in Central Park. The Strawberry Fields area by the Dakota is nice.
There are a lot of discussions about who has the best pizza, and those places are spread all across the city. Grimaldi's is in Brooklyn near the bridge, and if you go there you will have at least a 30 minute wait outside but it is absolutely worth it. If you go there, be sure to get the antipasto plate before your pizza, the peppers and cheese are terrific. Brooklyn Lager is a fine beer too. There is supposed to be a 99 cent slice place in Grand Central Terminal but we didn't go there; it's supposed to be pretty decent.
Gray's Papaya is a nice cheap eat - 2 hot dogs with kraut, onions, whatever and a juice drink for $3.50. There are vendor carts all over the city at just about every other corner with fruit, hot dogs, falafel, gyros, etc. There are a few delis in the Village that offer sandwiches for $11 or so with fries or chips, which sounds expensive until you find out that one sandwich will feed two people. Portions are large at most delis so sharing is not a bad idea.
We skipped the museums this time but the Museum of Modern Art and the Museum of Natural History are two of my favorites. You can easily spend an entire day in one of these museums and not see everything. There are smaller ones - the Jewish Museum had a great Warhol and Pollock exhibit a few weeks ago, it may still be there.
As far as architecture and design - you can see the Chrysler Building fairly closely from either the Empire State or Top of the Rock. The Flatiron Building on the way downtown to the Village is cool but kind of out-of-the-way. I don't know enough about architecture to point you around, but NYC is full of historical architectural styles.
As you get to the financial district is Fraunces Tavern, which is a museum that has a restaurant attached to it. It has been there since the 1700s and was an inn and tavern and meetinghouse for the leaders of the Revolutionary War. It was restored in the early 1900s and you can go into the room where Washington dismissed his generals after the British evacuated the City. Very cool.
The oldest bar in NYC is McSorley's, close to the Village, it has been in operation since 1854. They serve two kinds of beer, McSorley's light and McSorley's dark. We were there during the afternoon and I guess it was happy hour because it was 2 for 1. Both beers were very good and the bar is amazing, like a living museum.
The bar that stood out for me in the Village was d.b.a. I think they're supposed to have something like 400 beers and 80 whiskeys. Absolutely fantastic place with reasonable prices too. You'll probably want a cab out of there instead of the train.
I thought that going to Ground Zero was a must. After seeing it, I'm not so sure. It looks like a construction site. Fences all around, crowds of people looking at something that isn't there. On the southwest side of it is an enclosed walkway with a good view of the site but it's very depressing to see that so little has been done. It has been cleaned up, but there is no new construction and not much to mark what that area represents. It can be somewhat painful.
Take the subway trains. If you'll be there more than three days buy a seven day pass at the station and it'll save you money, time and trouble. Use cabs only when you're pressed for time or too drunk to navigate the stations.
I hope some of this helps. Check out the New Yorker online (
www.newyorker.com), get a New York magazine and a Village Voice and see who's playing where in town, sometime there are interesting literary readings at one of the universities. Good comics work at Caroline's if you're into that. Times Square is ridiculously crowded at all times but you need to stand there and see all the buildings, preferably at night for the full effect of all the lights and scrolling tickers, etc.
There definitely wasn't the feeling of imminent danger that I've gotten there before. When walking across the Brooklyn Bridge we did see on the traffic level below us a very large black man beating the living crap out of a very nerdy looking white guy. There was some sort of traffic altercation and the white guy might have rammed the black guy's car, but what we saw was the black guy halfway inside the white guy's window, landing hard left hook after hard left hook after hard left hook. Then a little walking around and yelling, then back for more pounding on the little guy who finally was able to drive off and was pursued by the black guy. No telling what happened later.
You'll definitely have some sort of "New York moment" if you're there more than a day.