This is what a friend told me before I went. He used to live in NYC.
"Restaurants:
Plenty of great places for brunch:
Extra Virgin in the West Village - can't book but if you get there just before 11am (weekend, or 12 during the week and with less queue) and hang around they let people in on a first come first served basis - excellent little place, great food and we sat next to Giselle for brunch one day. Not expensive.
Pastis - In the meat packing district (13th St and 9th Ave) - hotel can book for you - very popular and a cool atmosphere.
The Park - 10th ave and 18th street - big conservatory style space on the west side, close to the Highline elevated park and walkway - good to go and see, also close to Chelsea Market - worth a stroll through
Shake Shack - in Madison Square Park - simply the best burgers in town, but you have to eat them in the park - get there early to avoid massive queues,
Grimaldi's - cheap, crowded and truely old school Pizza house - a must for all pizza fans, but take cash and be prepared to wait in line and be underwhelmed by the decor, overwhelmed by the food. In Brooklyn just over the bridge.
Deli's - try these for lunch - less than 10 bucks will have you well fed all day for a sit-in place - famous ones include Carnegies on Broadway near Times Square (will be in most guidebooks) - however, stick your head in most places as you walk past, you'll be amazed at the selection of fresh hot and cold salad bars, sandwiches and salads etc - and they are excellent (don't be put off by any dodgy looking signage outside!).
Evening meals:
Rosa Mexicana - funky Mexican - there a few of them but the one nearest us was on 19th in between 5th and 6th I think.
Dos Caminos - another good mexican - a couple around town that the hotel will know.
Steakhouses - Expensive but well worth it - Porterhouse in the Time Warner building (nr central park) is a modern style one, but for true old school NYC steakhouses, try NYC Strip House on 12th between 6th and 7th ave (I think), Homestead (bit more relaxed) at 9th and 15th st, and of course Peter Luger in Brooklyn - where you can only pay cash, the waiters are rude and the place looks like a canteen, but the steaks are amazing.
Fig and Olive - in the meat packing or also uptown somewhere, nice little Mediterranean style food - funky bar at the weekend
Rare - burger place on Park and another in the Village / Soho on Bleecker Street.
Clearly - there are load more - if you're after something with a view - the River Cafe is just on the other side of Brooklyn bridge and offer amazing view of the Manhattan skyline at night - but book very early to avoid disappointment.
Activities:
Free Grand Central tours meeting at the clock in the middle of the hall at 12 on wednesdays
Statten Island Ferry - free, takes 30 mins to SI and goes right past the statue of liberty - cheaper than the special boat to Liberty and Roosevelt Islands
Highline (see above) - worth a walk up and down the west side of lower manhattan - its the old elevated railway line that's now been converted into a very long park.
Open top bus tours - the sales reps will stop you in times square - you'll see them.
Walk across brooklyn bridge (can do this and then get to Grimaldi's which is nearby, or RIver Cafe restaurant with great view of Manhattan skyline, then take subway back)
Stroll around Central Park (if you follow the internal ring road all the way round, its 10km, so best to meander through the inner paths of the park unless they fancy this hike accompanied by the runners and cyclers of NYC! Or a trip on a horse and carriage can be arranged from the south west corner of the park at columbus circle around 59th and 7th)
Shopping:
Bleecker street - a long row of local shops / boutiques
Historic Cast Iron district (in Soho) - anywhere between spring and grand streets, broadway, mercer, greene and wooster streets. Usual brands and nice area - back street have larger designer boutiques converted from old buildings. Nice to walk around.
South Street Seaport
Macy's (33rd and 7th ave)
Bloomingdales (63rd and 3rd)
Saks (5th ave and 49th)
Lord and Taylor - 39th and 5th
5th Avenue from central park (59th st) down to bryant park at 40th street, where the library is.
Century 21 - jumble sale style discount designer store - think "Next" sale at Xmas... (its near ground zero if you want to see that too, with the best view being from the upstairs section of the burger king on the corner - also go to St Pauls church nearby for a potted history of events)
FYI - for macy's, lord and taylor and bloomies, if you show your passport at the cust service desk they'll give you a 10% off card cos you're a foreigner and can avoid sales tax.
Drinks:
Too many great places to go to for us to list them all, but some good areas are:
Meat Packing District (look for Pastis again, Revel just down the road, One in the middle of the square, "Five 9th" in a dilapidated old building nearby and many more in this area - a picturesque cobbled road area which is very busy on fri and sat night (perhaps too busy), but well worth a visit and better on a weds/thurs if you can make it.
Lower East Side - Alphabet City - basically a bit more studenty but lots of fun bars, restaurants etc
Individual little places in the West Village on each corner - look up "the other room" for a feel of local west-village style casual drinking nights.
Soho
230 5th (the address and the name), it around 26th street on 5th ave, go in the bottom of an office building, bar is on the very top over two floors, with great rooftop views of the Empire State Building
Bryant Park bar - but the outdoor bit will be closed by November.
Treats:
Billy's Bakery cupcakes - 20th and 9th
Magnolia (the one from "sex and the city") - Bleecker St
cinnamon and sugar warm preztel from the sellers in Grand Central station basement
Lattes - from anywhere - but if you're near the library at Bryant Park go into a Deli called Zeytinz on 40th btwn 5th and 6th - its where I had lunch a lot - great sandwiches, great lattes, great kebabs (it run by Turks), great salad bar. Alternatively, Charlie's is over the other side of 5th, 40th btwn 5th and Madison."
This is also a great place to have a drink with a view. They even provide a sleeping bag coats for you if its too cold outside.
http://www.230-fifth.com/
If you only go up 1 skyscraper (Empire state or Rockerfeller), I would go to Rockerfeller so you can see the Empire State which is more iconic.
