Weddingbee boards

New York is great during the holidays, but it can get VERY VERY crowded. I would go to some of the more touristy spots during off times so you won't feel too claustrophobic.

Also NY is a walking city. You can walk anywhere, and you don't have tp stay in Times Square to feel like you are near anything. Honestly I understand the appeal, but as a lifelong NYer I stay away from Time Square because it's just so many people (ironic huh?).  It's still a fun cool place to visit for the first time. There is also the subway and taxis (although if you're looking to reduce costs don't take too many taxis). If you are not used to public transportation, especially rapid underground transportation, I honestly think the subway is a good experience. It's a very fast and economical way to get around town. Don't be intimidated by the map and the size of the subway.

As for activities especially holiday related I would try:

-Christmas Tree at Rockefeller Center Ofcourse (Go at an off time. It will get packed)

-The windows at Saks Fifth Avenue and Macy's

-Any of the following holiday shows: Radio City Christmas Spectacular, Cirque Du Soleil's Wintuk, NY Pops, anything at Lincoln Center (especially the Nutcracker ballet)

-Ice Skating at Wollman Rink (in Central Park with a gorgeous backdrop, where they filmed "Serendipity"), Bryant Park or Rockefeller (the last one I think is pretty expensive)

-open air markets selling lots of fun interesting stuff, check out the ones at Union Square (right outside the subway station) and Bryant Park

-I also think Grand Central terminal is pretty cool just to get a drink and people watch and there is a holiday market as well.

Get a Time Out Magazine. They have tons of listing for music, dance, nightclubs, etc. for the week and it's a great resource.

Feel free to PM if you have any other questions!