I have heard In the Heights is amazing and suggest trying Broadwaybox.com as well to see what you can get. I also agree about Radio City Christmas Spectacular. I took the kids a few times and don't understand the hype, but that's me. I think you should see the tree in Rockefeller and then do Macy's, St. Pat's and walk along 5th for awhile then go downtown to eat. The food in Soho, the East and West Village is usually better priced, better atmosphere and delicious. I would also suggest going to Battery Park. For a first time visit, its nice to see the great views Manhattan offers. Also, if you're downtown, a walk across the Brooklyn Bridge is beautiful if you can handle the cold. And while I've never been to the River Cafe, I hear constantly from New Yorkers and visitors that it is a great dining experience. You could even try brunch there, but you'd have to look into that as I don't know too much about it. However you do it, there is so much to do and see that I think no matter what you do, you'll have a great time. And as always, I have to give a plug to Katz on Houston Street. I went in a few days ago and still say its the best pastrami on rye ever! Enjoy!

Definitely River Cafe for view, romance and $$$$. Worth the splurge and In the Heights is fun, lively, also Billy Elliot (sp?) is another great show....Enjoy. We leave in 15 days for our long weekend in the Big Apple.....

River Cafe is VERY good food - not the best in NY - but very good. I wouldn;t do brunch -since one of the main attractions is the view of Manhattan lit up across the river as well as the pretty sight. I believe the prix fixe dinner is now about $100 - definitely worth at least that for the whole experience.

We had wonderful meals at Cafe Boulud and Le Bernadin while in NYC. We had a nice lunch at The Boathouse in Central Park while walking around yesterday. Pretty views and the ambiance is elegant. We loved our row boat ride around the lake there after lunch. ***kim***

Many historic house museums have wonderful holiday events that transport you to "Old New York". During your planned dates, The Mount Vernon Hotel Museum & Garden has Candlelight Tours that are very magical. It's only a few blocks from Bloomingdales so you could combine it with a trip to see their windows. Also in this neighborhood are Le Cirque, another classic New York restaurant, and Patsy's Pizzeria for real NY style pizza.

Check out(places to eat)
Dell'Anima
The Little Owl
Momofuko Ssam

all have young & hip patrons as well as some old folks like myself

See my trip report on NYC for some other ideas.

I'd book @ The Carlye and catch a cabaret performance as well.

Ok beware you may just pack up and move here. We did three years ago and love it. People are really great and helpful. Be prepared for the cold (hats gloves, long johns) and good walking shoes. Be sure to get a subway pass which allows you to ride the subway and buses (feet get tired hop on the bus and see some areas you may not have seen). Some other things that were not mentioned. #1 Chelsea market #2 Mario Batali's new E-taly market (sp). #3 Also NYC is full of great bakeries (look online for a good cupcake place must have a cupcake) I found it crazy that there are stores that just make cupcakes!! Magnolia bakery famous!!I found that a plan of where your going helps. It can be overwhelming. We went to Gordon's The Maze and thought it was great. There are also lots of great chocolate shops around (hello sweet toothe). Unless you really desire to go into the statue of libery wich is nice to see (the boat ride in the winter can be chilly). There is a bar at the Marriott Marquis and they have a revolving bar "The View" for $30 you can eat at a nice sorta tapas buffet and have a drink. Great view. Definately go into the hotels and the bars mentioned. FOR BATHROOM USE THE HOTELS FOR SURE. Have a great time. Grand Central is a must. So awesome to see. Also you may want to check out The Tenant Mues. and be sure to go to a Jewish Deli.