- Upper West Side — North of 59th Street, bordered by the Hudson on the west and Central Park on the east. Mostly residential, with some museums and a good portion of the city's top high-end restaurants.
- Upper East Side - North of 59th Street, bordered by Central Park on the west and the East River. Ultra high-end residential, high-end boutiques, The Metropolitan Museum of Art, and some decent restaurants.
- Midtown — Essentially the area between 59th Street and 34th Street. Tons of things to do, places to eat, and most of the tourist traps are also here. Solid place to stay because you can get to/from anywhere from here.
- Hells Kitchen - Basically "East Midtown", the area east of 8th Avenue. Mostly residential, though there are some decent restaurants and bars in this area.
- Chelsea — East of the Avenue of the Americas between 34th St and 14th St. Really swanky area, lots of outstanding restaurants, bars, nighlife, and residential.
- West Village / Greenwich Village — Greenwich Village is a small subset of the West Village which is south of Chelsea. This is the eclectic Bohemian part of New York. There is essentially anything and everything here.
- East Village — Directly east of the West Village (go figure), this is mostly Bohemian / very unique residential. Some great restaurants, a ton of amazing bars, and unique nightlife. It's an experience for sure, in many ways it's the cultural melting pot that forms the heartbeat of NYC — it's lost a bit of the "rapey, muggy, heroin-y" vibe, and replaced it with a lot of varying culture.
- SOHO — Stands for "South of Houston Street" (pronounced "Howston"), lots of shopping, unique boutiques, some decent restaurants. All around fun place to go shopping and walk around. South of this is Little Italy and Chinatown, so usually you can make a combo trip to visit all of these areas.
- Financial District — It's what it sounds like. This is the southern tip of Manhattan, where you get access to the Brooklyn Bridge, the World Trade Center, Battery Park, etc. Mostly business and business types, but increasingly some great bars and unique restaurants.
- Subway — true New Yorkers use the Subway. It's the best mass-transit system in the world, and if you can get comfortable with it, you can get anywhere in the city cheaply and quickly. I recommend buying a multi-day unlimited pass because otherwise you have to pay by the ride. There are two directions in New York: Uptown (north) and Downtown (south). Inside Subway stations, you'll see signs designating these two options—make sure you know which direction you need to go so you get on the right train. Subway lines are color-coded (orange, blue, red, green, yellow, purple), and trains are lettered or numbered (F, R, C, 1, 2, 3). There are two types of trains: local, and express. Local trains stop at every station while express trains only stop at major stations. You typically don't have to worry about which train is which, other than making sure both stop at your destination. If express trains blow through your destination, you'll want to make sure you grab a local. There are several Subway iOS/Android apps, but honestly Google Maps (turn on Transit in settings) does just fine — just keep in mind sometimes it won't work inside a station or train (service has gotten a lot better), so best to know where you're going before hand or check the map inside each subway car. The Subway is a little intimidating at first, but stick with it—once you get the hang of it, you'll be amazed at how easily you can move around the city.
- Cabs & Uber/Lyft — cabs are great, but more expensive, more apt to get caught in traffic, and difficult if you have large groups. It's rare to spend less than $8 on a cab ride unless you literally are only going a couple blocks, and that can easily escalate to over $20. Uber/Lyft is a bit cheaper (and a helluva lot nicer), though still more expensive than the subway. Now that Uber/Lyft exist, I rarely take cabs anymore. I will usually cab/uber/lyft it when we're going to/from an event, when we're tired, when my wife is wearing heels ;-), it's late, or we're late. If I have to go significantly east/west in the city, sometimes it's best to cab/uber/lyft it — typically Subway lines run uptown/downtown, so if you need to get from say 2nd Ave to 8th Ave, it might be easier to just hop in a cab, rather than have to train-hop in the Subway.
- Walking — NYC is the perfect walking city. The city is laid out on a grid, avenues run north/south (alternating one-way except for Park Avenue), streets run east/west (alternating one-way). Avenues are numbered from east to west (1st Ave is the farthest east, 12th Ave is the farthest west), Streets are numbered from south to north (streets numbers go higher as you move uptown). Typically addresses are given by cross streets ("48th and 5th" translates to 48th St. and 5th Avenue), and this is how you'll give your destination to a cabbie. Once you get that picture in your head (of the grid), it's super easy to walk around. Blocks are smaller as you move uptown/downtown, and larger as you move east/west (because there are more streets than avenues in the city). So just keep that in mind to avoid getting over tired as you walk around.
- I have recommendations below, but there is SO MUCH good food in NYC that I hardly ever eat at the same restaurant (unless I indicate it). It's fun to just discover new places, and NYC is the best place to do that. Set a value threshold, and just experiment. Sometimes you'll find a dud (I usually hit one every trip) but the majority is outstanding.
- See my Google List
- See my Google List
- See my Google List
- See my Jauntful list
- See my Jauntful list
On the whole, NYC hotel rooms are smaller (usually 400 sq ft is the max on basic rooms) than what we're used to say in Orlando or other cities, so keep that in mind. You're usually safe with most of the name brand hotels (Hilton, Marriott, etc), especially in Midtown. But then again, they're kinda boring as well. But really, you're just crashing in these rooms for the night...
- The Ace Hotel — 20 W 29TH Street — one of the coolest hotels in the City, great bar inside the hotel as well.
- Yotel — 570 Tenth Avenue — contemporary, cheap, European style in a great area
- DoubleTree Suites Times Square — Times Square — I've stayed here a few times, what's great is you can double/triple up on rooms to save money.
- Marriott Courtyard Herald Square — 71 W 35th St — I really like this hotel, it's quiet, in a great location (right across from Herald Square), and pretty reasonable. Rooms are small, but for what you get it's solid.
- Greenwich Hotel — 377 GREENWICH STREET NEW YORK, NY 10013 — A super high-end hotel with a super high-end price point. Owned by Robert DeNiro, this hotel has won several recent awards and every room is designed and decorated differently. It's like an Anthropologie store married Architectural Digest.
- Bryant Park Hotel — 40 WEST 40TH STREET — Mid-price hotel in a great location. You get the level of service and luxury of a hotel like Greenwich at about half the price.
- I prefer to stay in Midtown-ish as this gives you the most options for getting around the city. I like to stay closer to 34th St / Herald Square, or Bryant Park / 42nd Street east, but you can do the Times Square thing if you like as well. It's just a lot louder and more raucous, and you'll pay a higher premium...but it can also be fun.
- There are also some very nice hotels in the northern area of Midtown, closer to the Park.
- You can find some nice spots in SOHO, or on the northern outskirts of the Financial District, or increasingly in Chelsea, and TriBeCa.
- If you're AirBNB-ing it, I'd recommend finding an apartment in Greenwich Village, Chelsea, or Midtown.
- But what about Brooklyn you ask? Brooklyn is awesome, and admittedly I'm not as knowledgeable of Brooklyn as I am of Manhattan. If you're planning on spending most of your time in Manhattan, I probably wouldn't stay in Brooklyn because it's a lengthy Subway ride to get anywhere...if, on the other hand, you want to spend a decent amount of time in Brooklyn, there are lots of great AirBNB's to be had there.