I think it might also be nice to hit some "classic NY" hotel bars (i.e. the King Cole Bar in the St. Regis; the Algonquin down on 46th) and if you want a classic NY bar & restaurant, I love PJ Clarke's (it was my grandfather's local pub back in the day!) A lovely Champagne bar is Flute on 52nd (I think) between 7th & Bway. W hotels have some good bars too. Have fun!

Some more ideas: how about some of the historic literary bars of the West Village? The White Horse tavern (where Dylan Thomas had his "record number" of whiskeys & died the next day...), Chumley's (famous old speakeasy--no name on the door, gotta look for the number 86!), Minetta Tavern, Kettle of Fish....going over to the east side...you can't hit old NY bars without hitting the oldest: MCSORLEY'S! Go during the day, make friends, drink beer, order the crackers, onion, and cheese and have a blast!