Libations & Such
Speaking as a native:
If you want to see how we natives quaff overpriced martinis, try Olives at the W Hotel in Union Square. Virtually no tourists even though it's a hotel lounge. Definite celebrity spotting (high level, not soap actresses). It's luxe, chic and loads of fun. Dress for success. Best drink, espresso martini. Link for location:
http://www.starwoodhotels.com/whotels/search/hotel_detail.html?propertyID=1299
Never, and I mean never-ever, take a taxi. Walk, take the subway and take busses. NYC public transit runs 24/7/365, is fast, cheap and safe (no kidding). Its also filthy enough to have some character. Buy the one-day unlimited MetroCard. Works on subways and busses. NYC's the best walking city in the world. Don't be afraid to wear out some shoe leather.
Don't believe a single word the tour guides tell you on the Circle Line or various bus tours. They're making all that rubbish up. Great way to see the city, however.
Macy's during holiday spending fever is TFR'd. There's nothing there you can't get cheaper and easier at WalMart. In any event, it looks run down and cheesy. Want to gawk? Sak's Fifth Avenue and Bergdorf Goodman.
Real Shopping Bargains? Euro-imports at bargain prices? CENTURY 21! Right near the WTC site. Great place for you guys to pick up the totally unexpected gift for your girl at dimes on the dollar (they have extensive menswear departments as well). I buy most of my clothes here.
FAO Schwartz is simply BRILLIANT; you'll feel six yers old again - see the world through eyes filled with wonder.
Anyone's who's tired of the usual tourist ripoff scene in NYC (Times Square, etc), should feel free to IM me for something a bit different from the usual guidebook fodder. I haven't been to Times Square in..., I forget how long.
EDIT: What time do bars close? Way past your bedtime. Try Pravda on Lafayette Street (near Prince Street) in SoHo. No sign, little red light by the stairs leading underground to a Moscow subway station. Tasty snacks. Lafayette runs north and south; the bar is on the east side of the street.