I absolutely love the City, the energy, the bustle, the tall buildings. IMHO it is an "experiential" city, kind of like Shanghai, where there are key tourist attractions, but the best way to enjoy it is to be like the locals and live, eat, explore, for a few days.
Eat and Drink
I can't pretend to know the best of NYC food and drink anymore. However, I still know it's one of the best food and drink cities in the world (if not the best) and definitely take advantage of every meal you have!!
Chowhound, Zagat and Yelp will be great resources - just keep in mind grain of salt for the "user" generated feedback.
If you are not American, it's time to become acquainted with OpenTable (http://www.opentable.com/). Many high end restaurants in major US cities use this reservation platform to some extent, and it will let you make reservations 24 hours/day way in advance of your trip at the places where you definitely want to eat.
For the two cents that it's worth, here are my NYC Yelp reviews and eat blog posts. Don't have too many, and I definitely think there are better lists.
Grand Central
42nd and Park Ave (Metro North and subways 4-5-6-S)
I think this is the coolest train station ever. I might have a soft place for Grand Central because this was my gateway into Manhattan when I was growing up in Connecticut, and also my way home when I was going to see my parents when I lived in NY. The station has this amazing dome with constellations and light shows during the holidays. I still stop in my tracks and stare up every time I walk in.
I might also love this place because of The Oyster Bar. It's located down the ramps, halfway to the dining area on the bottom floor of GC. When you go in, turn right and sit at the bar, and order a clam chowder, some cherry stone clams, oysters, and glass of chardonnay. The cherry stones are amazing - enormous, meaty and filling (if you don't like the clam genre, this is not for you). Great selection of oysters and you have to try a real New England clam chowder once.
After the Oyster Bar, stop at Campbell Apartment. This is another hidden place within Grand Central. I believe this will be towards the east side of the station - you can get there from the side entrance by Lexington Ave, or winding through the corridors in the station. Big happy hour crowd, but I think it's a great uniquely NY bar.
Other "old school" NY
In the same genre as GC are a few places that I remember feeling super NYer-y and grown up at back in my local days...
- Bemelman's Bar - located in the Carlyle Hotel on 76th and Madison, Bemelman's has fantastic ambiance with a jazz pianist and murals on the wall by the illustrator of the "Madeleine" books. Also where Carrie took Louise in SATC movie :)
- Keen's Steakhouse - I won't even try to get into "best steak in NYC" discussion, but this is my favorite steakhouse as much for the atmosphere as the steak and mutton (which is a must-have). Start with a drink at their classic bar and get at least one order of the mutton with your steaks. 36th between 5th & 6th.
- Yankees Stadium - Ok so I am a little biased, being a Yankee's fan . And the experience is a little less "classic" in the new stadium. But I don't know what can be more New York than a Yankees game, if you are there from April to October. Pick up cheap tickets online and have a beer and hot dog at the game. Take the 4, B, or D subway lines to 161st St/Yankees Stadium.
You should definitely spend some time to enjoy Central Park. In the summer, look out for the free concerts, the Philharmonic, and Shakespeare in the Park. Go for a run around the Reservoir (E86-96th) or see the various gardens. Get a deli picnic (and perhaps a bottle of wine) and camp out on the Great Lawn. You'll see the iconic horse drawn buggies at the south end at 59th Street (though you might smell them first)
Also, though not Central Park, Bryant Park at 45th and 6th has a fantastic free film series in the summer and ice skating and other activities through the rest of the year.
The Arts
New York might be the best in the world if you like the arts. I am not super artsy but I love being able to go to a symphony or ballet or jazz or an exhibit any day and with so many options.
Check out Lincoln Center for what's playing there, or Carnegie Hall. Jazz at Lincoln Center is fabulous. They have some great spaces and programs in the Columbus Circle Time Warner Building. The Allen Room space is phenomenal, with the Central Park and NY skyline in the background as the sun sets during the jazz show. Dizzy's is another great space, and you can make reservations on OpenTable (see below).
Obviously the Metropolitan Museum of Art (the Met) and the Modern Museum of Art (MoMA) are two of the world's best, with a great permanent collection as well as special exhibits. So many smaller but fantastic museums and galleries. Definitely check out listings when you get in (see NY mag below).
Don't think it's considered the "arts", but I also love exploring the Natural History Museum on the upper west side. One super cheesy but educational and fun was to enjoy this museum (as well as a bunch of others now) is Watson Adventures' scavenger hunts, two hour whirlwind group competitions to answer clues based on what you can find at each site.
Touristy New York
If you have to do the touristy things in NYC, here's my mom's NYC one-day tour she takes Japanese visitors on.
Start at Battery Park, take photos of Statue of Liberty. Ground Zero site is blocks away, then walk around Wall Street. Head north to Chinatown for dim sum lunch, then up to midtown to see the UN on the east side (42nd-46th and 1st Ave), Empire State Building (34th and 5th Ave), and walk on Fifth Ave. On your way out of the city, relax at the Cloisters.
Etc.
*Buy a New York Magazine first thing when you arrive in the city. Magazine has the week's schedules for shows and exhibits in town, as well as great restaurant lists. The website's Restaurant section might be helpful.
*Use the subway. Super convenient, runs all hours, pretty clean and safe (usual precautions), and as cheap as NYC gets.
*If you are coming from elsewhere on the Eastern seaboard, consider taking Amtrak into Penn Station. LGA and JFK are both outside of Manhattan and can be lengthy cab rides depending on time of day, and the trains don't have the hassle of air travel with similar or cheaper fares.
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