And so will you!
I second the tip about the weekly pass - the subway is really easy compared to the London tube, for eg. - it just goes north/south at busier streets, roughly every 2 blocks (and with stops roughly every 5 blocks north/south), with east/west connectors at 14th and 42nd Streets, be careful you don't get on an express by mistake. Streets go east/west, numbers increasing as you go north, starting in the Village (below that they have names), with address numbers radiating out from 5th Ave (ie at 5th they are in the 100 block east and west, numbers get bigger the further out from 5th ave you go), avenues go north/south - a north/south block is about one and a half times an east/west block so yeah, good walking shoes a must!
A fun thing someone who came to visit me once did was walk all the way from brooklyn (across the brooklyn bridge) north to central park - takes a full day but you see lots. Great shopping neighborhoods - SoHo (love those cast iron buildings, esp on Mercer and Greene), Broadway at the Village (go north from the arch on Greenwich park), lower Fifth Ave around 15th and 16th streets, midtown near Bloomingdales (Lex., Madison or Fifth around the 50s) and the Upper West Side, on Broadway, north of Columbus Circle up to Zabars, around the 70s and 80s. And, if you like street shopping, Canal St in Chinatown. If you want to go to FAO Schwartz, avoid the Park Ave entrance and go in the back, on Madison, where there is no line.
Food to try:
2nd Ave deli - on 2nd Ave, at 12th street - great matzo ball soup and corned beef on rye sandwiches
Yama sushi - various locations in the Village - on Houston at 6th and on Carmine Street
soup nazi - 55th st, between 8th and 9th Aves, I think
best pizza in the world - Grimaldis under the brooklyn bridge!
best bagels - H&H, on the Upper West Side
great brunch - Isabellas, also on the UWS, near Central Park, long wait on weekends
cool "fusion" place - Elephant, on 1st Street at 1st Avenue in the East Village; also Dok Suni (korean) on 2nd Ave.
expensive but awesome - Le Cirque 2000, Asia de Cuba, Daniel - a lot of these expensive restaurants do, however, have prix fixe lunches that match the year (ie this year, $20.02, plus tax and tip), eg Gotham Bar and Grill, Union Square Cafe, etc. - check with them.
Tipping - I usually double the amount of the tax - in NY state tax is 8.25% so the tip I leave starts at 16.5%, you can go up to 20% if service was incredible (but only if) - I tip cab drivers less, usually $1-2.
Interesting bar - Bar 89 in SoHo (use the restroom at least once - you'll know what I mean!). The revolving bar at the top of the Millenium Hyatt in Times Square is cheesy but fun!
Avoid
- buying/ eating anything in over-touristed Times Square
- Hells Kitchen at night (around 9th and 10th Aves in the 40s, near the Port Authority and north)
- park in Greenwich village at night (the druggies still hang out there I believe)
- standing too close to the edge on subway platforms
Be warned - it will be cold - dress appropriately! And don't be afraid to strike up conversations - New Yorkers are friendlier than people give them credit for!
Have a great trip and let me know if you have more specific questions!