Ground Zero.
Go there and grasp that it's real.
It's not about politics. I'm neither a Bush nor a Clinton fan. I'm an independent. Anyone who wants to make a political comment - take to a separate thread and we can talk politics, war whatever there.
About a half hour before sundown I used to advise people to go to the Top of the World (Twin Towers) now the Empire State Building (102nd floor if it's open) or the TopoftheRock (I've not been there). Any tall building with a view. Watch the sunset over NJ. Then watch the fireworks as Long Island turns on. Then Broadway erupts in lights! Then NJ lights up. Pardon the pun but it's electric.
Dinner depends upon your budget, hotel, and schedule, your age, and companions. There's a neat restaurant under the Brooklyn Bridge. The RiverView. It's on a barge with an unobstructed view of lower Manhattan (aside from the Brooklyn Bridge). It's also a great place to see the light turn on but not as dramatic as 1000 feet or more up in the sky. Dinner is fixed price. Will run you about $100 a head. With a wife or girl friend - a winner! A bunch of baskeball buddies - you're wasting "a moment" and your wallet.
In the theater distric there's a place called "Um De Twa" or whatever "one, two, three" is in French. I don't recall the spelling. They cater to the theater trade, "I need to be out of here for a show at 8:00!" They'll feed you before or after the show.
It's been awhile but the dinner and view was nice from The Top of The Sixes. (The building with the mark of the beast - 10 foot high numerals, 666. I think it was the dinner rejection site for the shot of the Empire State Building red heart in "Sleepless in Seattle".) The 21 Club, 21 West 52nd, was a Roaring 20's SpeakEasy. You can get a tour if you ask. Figure on reservations at any NYC place. Book them now if still available.
As you'll be there in Christmas Season, definitely Rockefeller Center. Besides the skating (say hello to Promethus), you can buy Christmas presents (small pocket sized stuff or big stuff) at the Museum of Modern Art Store in the complex. They will ship. Nice stuff for wife/girl friend/kids/folks. If you like architecture, go into the BIG building behind THE TREE. Check out the lobby art decco and the frescos. You can spend hours if you really like that stuff, if not 15 minutes. It's history and you won't see it in a Hilton or Holiday Inn. The Rainbow Room on the 65th floor.
When you're done go across the street to Tiffany's. They used to have some little things for $15 - $20. "Yes honey, I told you some day I'd get you something from Tiffany's. Won't that ornament look great on the our Christmas Tree! (You did think about her on a BB weekend!)
Down the street (if I recall correctly) St Patrick's. Easily walkable.
The other way (north) is Tavern on the Green (Central Park). It's nice at Christmas but crowded. Not a BB buddy thing. (Well depending upon upon how you define "buddy". This is the new millenium. If you still mourn John Lennon, The Dakota's not to far away, on the West Side.
Lots of art museum's. A little one on the East Side of Central Park is The Frick. An oasis in the Big City. Again not a BB buddy thing. But if your spouse wants to spend the day at MOMA, the Guggenheim, or such this can be a compromise. I don't know if The Plaza restaurant is still open. The hotel went condo. If the restaurant's still there you are with female companionship - it's a point scorer and just south of Central Park. Dinner or just "High Tea" (aka a marital harmony moment that you will never be asked to do again).
Haggle over a cheap fake rolex with an illegal street vendor. Buy a hot pretzel from a push cart.
Take a ride on the Staten Island Ferry at night. Dress warmly.
Statue of Liberty (the view from the top isn't as impressive IMO as the Empire State Building
Do NOT walk through alleys in the City - day or night.
Do NOT walk through Central Park at night even with a dozen guys.
Do NOT go in any park at night.
Do NOT all get drunk on a pub crawl and stagger back to the hotel room. You may wind up with hangovers and no luggage in your room. I knew a group of guys that made a similar trip. Their team one and they tied one on. Sang all the way back to the hotel and through the hotel lobby. Woke up the next day with nothing. Nobody thought to lock the door (they were all drunk and all wiped out - wallets, watches, etc).
If it looks questionable - avoid it. IF you don't know the neighborhood, spring for a cab.
Have you got a stockbroker?If you're a good enough customer (or Dad or grandad is make a call) a tour of the Wall Street market, a "free" lunch, dinner, or a show could be in the making, if you're interested.
ChinaTown, Little Italy, Tribeca, Soho Gallery's, McSorley's (I'm Irish) - hit the internet!