Hey... 20 year NYC "local" here- you're going to have a blast no matter what you do; some general advice:
Basic Rules:
- Avoid looking like a tourist, ie: blocking the sidewalk while you look fearfully at your map. The fear and overt touristy things are like infrared bullseyes for pickpockets and panhandlers.
- As you would while driving, try to stay to the right while walking- people are in a hurry here.
- Don't be afraid to ask for help on the street- people hate tourists, but love to help... it's that neurotic NYer thing.
- The subways are safe and a great way to get around (you can get an unlimited one week Metrocard for some savings if you intend to use the subway more than twice a day). Just avoid rule#1- substitute the doors for the sidewalk- and be sure to grab onto something to hold to avoid falling into the surly 300 pound Russian immigrant's lap.
- If you take a taxi, don't try and wave down every single one... the ones that are available have a light on in the middle of a screen at their top (2 lights on either side of the middle means it's off-duty). No light on means it's taken.
- Walk. Pick a neighborhood and walk all around- try linking it with other neighborhoods. This is the best way to see the city.
- Imagine that there will be a vacuum hose attached to your wallet, essentially sucking money from you all day. Every bodega has an ATM, so you can always reload.
Now that you know the rules.... some sights...
Manhattan Neighborhoods (from North to South):
-Inwood... North tip of manhattan, residential, but has the Cloisters- an old monastary(?) shipped over from Europe. Kinda cool if you've got enough time. Can combine with a trip to Yankee Stadium in the Bronx and/or a trip to Harlem.
-Harlem... resurgent lately, with some good restaurants and places to see music. I never go up there, so others will have to tell you specifics.
-MorningSide Heights... Columbia University (cool to see an Ivy league campus in the middle of NYC) which is right next to the Cathedral of St John the Divine- largest Gothic cathedral outside of France (maybe anywhere). Pretty amazing if you like that kind of thing... can combine with a trip to the Boat Basin and/or Upper Central Park.
-Upper West Side... nothing much to see except for the Boat Basin, on the Hudson River at 79th St. Intended as a bustling ferry terminal by Robrt Moses, now a houseboat marina that has a place where you can sit out in Riverside park with some drinks and some burgers and watch the sunset. Popular young couple/single scene.
- Central Park... Lots to see- highlights include Belevdere Castle on the East side and Strawberry Fields/ The Dakota Building (Where John Lennon lived/died) on the West.
- Upper East Side... The museums on upper 5th Ave: Guggenheim, Met, Frick, Whitney (see below)... and lot's of shopping on Madison ave (ie: expensive designer stores... Tiffany's, Bendels, Armani etc wife might enjoy a day of it. Can combine with a trip to the Met/ Central Park
- Midtown... Times square, The UN (all the way East), MOMA, Broadway theaters, Shopping.
- Hell's Kitchen... Used to be one of the roughest places on the planet, now cheaper rents making it gentrified. in the 30s and 40s west side- lots of bars/restaurants. Very up and coming area. Visit my friend's bar called "Pergatory".
- Chelsea... the main Gay area in NYC. Bars, restaurants (you don't have to be gay), and a alot of the bigger clubs (stopped going to clubs a long time ago, so somebody else will help you there). This is also the main Art scene in NYC- if you're around on a thursday, head over and check out all the gallery openings- free wine and snacks, and lots of pompous "art" scene people. Maybe even some good art too (not likely).
- Murray Hill/ Grammercy Park... Grammercy Park is kind of cool to see- private, gated park surrounded by old NY buildings. Feels like you're in a period movie.
- Union Square... Bustling area with lots of shopping, bars, restaurants, movies, theaters. Kind of like the Times Square for locals.
- Meat Packing District... Until very recently where meat was packed and shipped.. a couple of random bars/clubs here and there. Now- the only meat you'll see is what's stuffed into expensive clothes, cars and clubs. Lots of the trendiest bars, restaurants and clubs within a few blocks. You want trendy- this is the place to go (I won't go near it, but I'm not trendy).
- West Village... Used to be the gay area, now the yuppie area. Manhattan goes off the street grid here, so it gets confusing, but it feels more quiet and "quaint" as a result. Old brownstown townhouses and trees line the streets, some of them still cobble-stone. Nice shops, restaurants and bars.
- Greenwich Village... See Washington Sq park, the home of NYU and lots of skateboarding, juggling, drug-dealing kids. Bleeker street has lots of bar/live music joints for visiting teen-agers.
- East Village... More bars and restaurnats than you can shake a stick at... 2 new ones will open and close during your stay. If it's drinking and relatively cheap eats you want- this is your place. Ogle at Tompkin's Sqaure Park, previous home to a shanty village and anarchists, now to carriage strolling yuppies. Don't miss CBGBs where punk music was created- and closing it's doors (maybe moving to Vegas!?) in Oct.
- Lower East Side... My turf. This is where most immigrants lived in the early 20th cent in squalor... now it's where you have to line up got get the best pancakes in the city. Great bars, live music, Tapas restaurants, shopping.
- Chinatown... If you've never seen a Chinatown elsewhere, see one here. As you might imagine, everybody's Chinese, as are all the stores/restaurants, thus the name.
- NoLita/ Little Italy- Not much left of little italy, and what is is geared for tourists. Don't waste your time eating there. NoLita (North of Little Italy), is more worth seeing- SoHo has pushed East due to rents, so you get a lot of smaller shops, bars and restaurants there.
- SoHo... Used to be where the artists all lived in their great big lofts in their original cast-iron buildings. Now its the mall. But it's worth seeing. Shopping, shopping, shopping. Visit my friend's place MercBar (I met some serious supermodely/rock'n'roll/actor types there when it first opened long ago). Don't forget to look up at the great old buildings (in fact- that's true of most of NYC).
- Tribeca... kind of like Soho, but without the shops. Some bars and restaurants.
- Downtown... Don't miss seeing Ground Zero, where disgustingly very little has happened. Across the street is best bargain Dept store in the world at Century 21. Your wife will thank you, and if you need some clothes of any kind, you'll thank yourself. Walk across West St to the Winter Garden and then walk down the Hudson River to the Battery- nice views of Jersey and the Statue of Liberty. If you have time, take a round-trip on the Staten Island Ferry without getting off in SI- goes right past the Statue of Liberty and gives great views of the Lower Manhattan skyline on the cheap.
Museums:
- The Met... If you're interested just a little in art, go to the Met which is huge and has a little bit of everything from ancient relics to modern art, including the "temple of Dundur" which was brought over from Egypt (must see, if you go there). You could spend an entire day in there or just cruise through, heading towards the things you're most interested in. A great overview of art. You can combine a trip here with a trip to Central Park (as you can with the Frick and the Guggenheim)
- MOMA... If you're into modern art, MOMA is a must see, it's got most of the modern "classics" from around the world that you've only seen in books, and many others that will become your new favorites.
- Other museums that are cool:
-The Guggenheim... Can see this from the street and lobby without having to pay for tickets. Not a good spot to see art (as it's mostly displayed along the ramped walkways), but a must-see building.
-The Whitney... If you already love modern art, and are tired of the classics, or just loved what you saw at MOMA, go to the Whitney which is more current, and more out there. I love the building.
-The Frick... if you care who Vermeer is, you must go here. In an old Mansion right on 5th Ave (near the Met and the Guggenheim).
-PS1... if you're feeling adventurous, and somewhat into very current art, take the subway out to Queens where PS1 has continuous exhibits of some really wacky stuff. Artists in one year residence provide a lot. If you go on a Saturday afternoon, there are DJs and a very cool scene out there- well worth the trip.
-The Noguchi Museum... Long Island City, Queens- if you like Noguchi- this is where he worked, now a museum.
-Tenement Museum... See how people used to live in NYC. Very cool. Located on Orchard St in the Lower East Side. Go in the afternoon and combine with going for dinner/drinks out in the most up and coming neighborhood in NYC.
Restaurants:
- Pizza... Gotta say, there are so many it's tough to really differentiate. I like John's on Bleecker for takeaway, but it's much the same as Ben's in SoHo. Little Frankie's, in the East Village, has good sit-down thin-crust.
- Burger... (in best highlander accent) There can beee only one- and it's The Corner Bistro in the West Village. Dive bar with cheap and unreasonably good burgers.
- Sushi... So many places... Tomoe in the Village (Sullivan st?) is out-and-out the best stuff for the money. They have their own fishing boats, so always get the freshest fish. Plus it's incredibly cheap. Unfortunately, every NYer and Tourist in the world knows this, so there's always a line out the door (hour plus wait). I haven't eaten there in years as a result. Wife and I go to Cube 63 on Clinton St (L.E.S) for consistent and amazing sushi. (Clinton St is home to a billion BYOB tapas type places).
- Deli Sandwich... Alidoro (Sullivan St- SoHO) is the current home of the previous Sandwich nazi Melampo's. Stay to the left and stick the menu... or risk expulsion. Parisi Bakery (Mott st- NoLita) is an old-style bakery that puts out incredible sandwiches (italian style).
- Deli... Avoid the Carnegie and the Stage and the newer tourist joints mid-town (Artie's)- go to the real deal in the L.E.S and give me a wave fromKatz's. Get a ticket, proceed to the counter and don't ask for whole-wheat. Pastrami to die for (literally).
- Bar... I mentioned two that my friends own MercBar, Pergatory. There are an infinite amount of bars, so pick a neighborhood and find one that works for you. Oh yeah!... Try Angel's Share on E9th St and 3rd Ave. You have to go upstairs into a Shabu-shabu restaurant and through an unmarked door to get there... it's Japanese elegant with lots of crazy rules, but worth it, and fantastic mixed drinks.
There are a ton of restaurants and bars... if you're looking for something specific, let us know (ie: Indian restaurant row on E6th st).
If you have the time, check out Brooklyn or Astoria Queens. You can walk across the Brooklyn Bridge, take the subway back- see some spots. I'll let locals from those hoods share with you, as we don't have our travel-visa in place for such trips.
{{Edit to add}}
- Best Pancakes... Clinton St Bakery (Clinton St & E Houston) was our local spot, until the entire world found out about it. I've never had pancakes so good- but like Tomoe Sushi, over an hour wait to get in (on weekends)- I get furious everytime we want to eat there but can't. Try it on a weekday.
Also- Summer time brings all kinds of free concerts all over the city in the parks... check about them before you come, you might be suprised to see some of your favorites for free.