Guide to NYC
Some quick disclaimers: I clearly don't know everything about NYC. Most of what I do know is about the bottom half of Manhattan. If you just want a quick list of things to do in a couple of days, scroll towards the bottom. Thanks to Debbie Blair for co-writing.
Geography of Manhattan that is. As you can see in the map embedded below (more about that soon), Manhattan doesn't point north, but at an angle to the east. Handily though, on the island the compass is reinterpreted to line up with the island. So you have uptown / north, downtown / south, east towards the East river (and Queens / Brooklyn), west towards the Hudson river (and New Jersey).
An easy way to learn the geography is by the neighbourhoods. I have drawn them in crudely in this map below. Note: these are not strictly accurate (although no neighbourhood map really is), however they are reasonable approximations, and I will use them for food/drinks and things to do.
My advice: walk or get the subway. Taxis are expensive and can be slow - depending on the traffic, they can be ridiculously slow. Bikes are probably not a great bet as a tourist, but it's not impossible. Cycling can be fun in NYC, but perhaps not as a means of transport.
Most subway lines in Manhattan run generally North-South. Be careful, you sometimes need to enter a station from the correct side of the road. Luckily there's almost always a big sign saying UPTOWN or DOWNTOWN on the entrances.
If you have "data", i.e. internet on your phone, Google Maps has a fantastic transit planner. Else you can slightly pre-plan your subways, or just use the maps at each station. Connections are free. To pay, you buy a Metrocard and load it with credit. Generally you have some amount of time to make your transfer even if you need to swipe again (e.g. to change lines that don't have an underground walking connection, or to take the bus).
Eat / Drink
Head to the food page! Food in NYC
Things To Do
There are a billion things to do in this ridiculous city. I cannot offer anything resembling a complete list.
Often, some of the most interesting things to do are temporary. The best way to find out is to keep an eye on websites dedicated to such things, such as:
Other places include Timeout, which can lean towards the generic, but isn't bad, and http://www.reddit.com/r/nyc/, i.e. the NYC subreddit on reddit.com (can be an awkward website to navigate initially); they have a solid FAQ section. Really I suppose there are huge numbers of resources online for such things, but we are all operating on finite time...
Times Square [wiki, map] [plaza, theatre central, "center of the Universe", not a square] much loved and much despised. If you go to NYC, you have to check out Times Square at least once (and some would say at most once). One of most interesting people-watching locations in the world. Nearly all Broadway theatres are nearby, and there's a TKTS booth on the main plaza selling discount (although not much of a discount) tickets. To save money, check out rush tickets, explained in the shows / theatre section.
Bryant Park [website, map] [park, lots of events] a beautiful spot right in Midtown. The flagship library of the New York Public Libraries is here. It's fun to be in a gorgeous park with skyscrapers all around you - I think this park fits that description more than any other. Tons of events on here during the summer, including movies shown on their large screen, and free performances of songs from both Broadway and off-Broadway shows. Oh and food events! Keep an eye on the website (and the other general event websites linked near the top of the page).
Empire State Building [website, map] [building with observation deck] probably a little too famous... The views from here are excellent (although second to the Rock in my opinion), although not cheap, and you'll have to queue. Great at night: both to look out from, and to look at. They often light the building up in cool patterns etc. Can also be used for navigational purposes!
Rockefeller Center [website, map] [building with observation deck, plaza] the main thing here is definitely going up 30 Rock for the view. It's probably the best view you can get in NYC, since you can see the Empire State building, and Central park! Try go up just before sunset - the queues are usually not too bad, so you shouldn't have to go too far in advance. The rest of the plaza is nice but not too exciting. There's a Magnolia Bakery nearby if you're interested.
Grand Central Terminal [wiki, map] [train station] a gorgeous train station. It's the largest station in the world by number of platforms. There are some great tours (go with the Justin Ferate tours! explained further in the tours section) that go through here, and the building has a few surprises (e.g. echo walls!).
Museum of Modern Art | MoMA [website, map] [modern art museum] probably the best modern art museum there is. Free (pay what you want...) entry on Fridays, from 16:00 till 20:00, but you'll have to queue (and deal with larger crowds inside). Even people who don't like modern art usually find something of interest here! The MoMA design store is also great.
Museum of Arts and Design | MAD [website, map] [museum of objects / contemporary makers] a celebration of the art and design of objects and other "made" stuff. I think it has two free (pay what you wish) days: Thursdays and Fridays from 18:00 till 21:00. A fun, small-to-medium size museum with an always-changing collection.
International Center of Photography [website, map] [photography museum] small but solid photography museum. Also has free Friday evenings, from 17:00 till 20:00. It's not even that crowded during the free evening, so it's a good idea to wait. You might need some prior interest in photography for this museum.
Grand Army Plaza [wiki, map] [plaza] a bunch of fun things nearby. FAO Schwarz toy store is the US's oldest, and it also has an overpriced but excellent sweets/candy section. There's an Apple store here with a sweet glass cube entrance. You're also right at the corner of Central Park, one of the larger entrances. If you came to NYC to shop, this is close to a huge number of stores.
United Nations plaza [website, map] ["center of world politics"] official headquarters of the UN. To go on a weekday, you have to book in for a tour on the website. On the weekend, you can stroll in (I think). If you have the time for it during your stay, it's not bad. Interestingly, it's not US soil - it's international soil!
Madison Square Garden [website, map] [stadium, not square] stadium of the New York Knicks basketball team and the New York Rangers ice-hockey team. Often hosts gigs and so on. Games in NYC are expensive!
Downtown / Financial District
Brooklyn Bridge [wiki, map] [bridge with pedestrian section] the iconic bridge of NYC! A beautiful old bridge, definitely worth a walk across. You get great views of Manhattan from the bridge, and even better views in Brooklyn near where you get off on the far side. There's also a decent bunch of things to do on the far side. Quick note: the entrance to the bridge on the Manhattan side is close to City Hall, not actually right at the East river.
Staten Island Ferry Terminal [website, map] [ferry terminal] this is the ferry terminal for the FREE ferry to Staten Island. Get to the right hand side on the way over for views of the Statue of Liberty - or stay at the back for views of Manhattan. Then reverse these directions for the way back. Not sure if Staten Island has much to offer over Manhattan sadly: we just took the ferry over and right back. Check the site for the schedule.
9 / 11 Memorial [website, map] [memorial at Ground zero] worth a visit. You have to queue to get in here, as you pass through airport-style security (no body scanners though). You can either get your tickets beforehand from the museum (or elsewhere) or just join the slightly longer queue if you don't have a ticket. Pretty powerful memorial.
Wall Street [wiki, map] [street, NYSE] while now slightly outmatched by Midtown in terms of dollar volume of business, it's still an important financial center, anchored by the New York Stock Exchange. Most of the street is pedestrianised, European style! Well, the whole of downtown Manhattan is ungriddy...
Charging Bull [wiki, map] [sculpture] (note that Google maps is slightly wrong: it's at the top of Bowling Green) the bull! Always crowded with tourists. A pretty sweet sculpture though, worth a look.
New York Classic Theatre [website] [moving theatre - in both meanings] this great little theatre group puts on a couple of different plays every summer, set somewhere in NYC. You'll have to check to see where and what! The best part is that they move around their location during the play. After every scene, the whole play moves, and the audience gets up and moves with them. Great fun. And FREE! Although they do recommend a donation.
Shakespeare in the Park [website, map] [FREE theatre: all Shakespeare] this is where the free Shakespeare in the Park happens. It's excellent! You sadly have to do some severe queueing to get the tickets though, but it's not too bad. One person can get two! Or you can pay $200 a ticket. Check around for details on when this happens (basically in the summer) and when / where to queue etc.
Walk - this one is pretty obvious. The park is a little more active down lower, but it has neat parts everywhere.
Cycle - there are much better bike rental spots than the guys situated at the entrace to Central Park. If you're shorter on time, they can be a good idea, but try to shop around a little if possible, they're not all a complete rip-off. We in fact trekked down to Waterfront Bicycle Shop [web, map]. It's not very close to Central Park, but you can... cycle there!
Upper East Side (UES)
The Metropolitan Museum of Art [website, map] [art museum] a massive excellent art museum. Its' FREE! Well, it's pay-what-you-wish. All the time. They don't really make it obvious, and you have to pay at the desk - the computer machines don't let you pay less than the "suggested" fee - but it's always pay-what-you-want. We went with $1... Don't feel bad, they don't pay rent! Actually that's why it's free.
Whitney Museum of American Art [website, map] [art museum - avant garde American] American art, mostly of the last 100 years. This museum is moving at some point in the near future, check before you go! The current space is great though.
Roosevelt Island Tramway [wiki, map] [cable car!] if you have time, this is a fun trip across to that weird island between Manhattan and Queens. The trip is probably better than the island... Offers pretty solid views of Manhattan as you go across!
Chelsea / Meatpacking
High Line Park [website, map] [park build on elevated train line] a fantastic example of repurposing: what was an old unused elevated train line is now a gorgeous unique park. An NYC must-visit. They run some free tours and such here, check the website for dates / times.
Chelsea Piers [wiki, map] [piers, park, walk] the real story is actually the area just above the piers (from about 22nd street and up), with some lovely park areas that have events on during the summer (keep an eye on those links!).
Flatiron District / Madison Square Park
Madison Square Park [website, map] [park, almost a square] the location of the original Shake Shack! And much more: another fantastic park. Nearby is the iconic Flatiron building, worth a look. A lovely park to while away a few hours (for example with travel scrabble).
Union Square Park [wiki, map] [park, plaza] both a park and a general plaza. Usually there's loads of stuff going on here: food trucks and markets during the day (not every day), people bouncing around at night. Not necessarily the most beautiful spot in the city, but a bustling area nonetheless.
Upright Citizens Brigade Theatre East [website, map] [comedy] the East Village location of this comedy group: very cheap excellent comedy venue - something like Chicago's Second City venue. Lots of improv and stand up etc.
Tompkins Square Park [wiki, map] [park, is square-shaped] an eclectic park, can be a bit rough, but a nice varied park, with some basketball courts and so on too. Hosts decent events during the summer, keep an eye on the links!
St. Mark's Place [wiki, map] [street] essentially this is 8th street. A huge selection of food and shops here. It's another love/hate spot for many locals - lots of night life and people watching here too.
West Village / Greenwich Village
Washington Square Park [wiki, map] [park, NYU] gorgeous park near NYU (very near... You're surrounded by NYU buildings!). Like a lot of NYC parks, many summer events take place here! Keep an eye on either their websites or else the usual ones given up near the top of this page to see what's on. Lots of great food around here, and lovely areas to walk (West / Greenwich Village in general!).
SoHo / Tribeca
SoHo galleries [website, map] [art stores / galleries] there's a whole heap of stores / galleries in SoHo. There's a map provided there, but it's probably more fun just to wander around and pop into any that suit your fancy.
Shopping [map] in my opinion, this is the best shopping area of NYC. This depends on what types of stores you want to go to, but there are so many excellent little shops around here. There are flagship stores for brands, and also stores like Opening Ceremony selling all sorts of dope stuff. I guess your best bet is to browse online fashion forums etc to find the best shops to suit your interests.
Upper West Side (UWS)
Lincoln Center for the Performing Arts [website, map] [multiple performing arts institutions] lots of big name performing arts institutions here, such as Juilliard, Met Opera, NYC Ballet and NY Philharmonic. Free events are sometimes held here during the summer. On that website link you'll find the regular event schedule.
Columbia University [website, map] [university] (this isn't actually in UWS, it's in Morningside Heights (just above UWS), but there was no need to further complicate the issue) one of the US's best universities. Very pretty grounds, worth a wander if you have a chance to get up here. There's a campus tour you can do, but really it's only useful if you want to see the library, the rest you can just walk around for. I hear you can go up the church nearby and get great views, and see their sweet carillon, which I believe is the world's largest. Not much else going on in this part of town.
The Cloisters [wiki, map] [museum - rebuilt monastery] part of the Met museum: your ticket can get you into both. Or again, it's pay what you want. It's basically a bunch of European monasteries that were shipped over and rebuilt. Curious thing. Maybe not especially exciting if you're European... But still. It's also an actual museum inside, with medieval art. It's pretty far north in Manhattan, but the subway takes you close.
Fort Tryon Park [wiki, map] [park] this is the part that contains the Cloisters (above). A nice walk if you're on your way to the Cloisters. Nice views of the Hudson from here, and you can almost imagine what the area was like before anyone moved here.
Lower East Side (LES)
New Museum [website, map] [very contemporary art] if you're a huge fan of either contemporary art, or of whatever artists they're currently exhibiting, this might be worth a visit, otherwise the reviews aren't superb. Interesting building to look at from the outside, but not worth a trip by itself.
New York Bay
Ellis Island / Immigrant Museum
Statue of Liberty
Museum of the Moving Image [website, map] [museum of media: film, television, digital] a great little museum, full of fun things about film and film history, as well as some great interactive exhibits. It's a bit like the EMP museum in Seattle, but with a film focus. I'd say it's definitely worth a visit - with the only caveat being that it's slightly further away than a lot of museums (I guess this is all relative).