If you had two days and three nights to fill in New York City, what would you do?

I’m a museum fan, so I would find a bunch of odd little museums here and there, but you can do a whole day in the Metropolitan and/or the American Museum of Natural History if that’s more your thing. I would take in a play at a small theater or two, I would wander into Chinatown for lunch, I’d hang out in the Public Library for a bit.
The site Hopstop.com gives lots of good info for getting around, whether by foot, cab, or public transit.
Go to Grand Central Terminal and gawp at the ceiling.
Have fun!

I would see a show. Great vocal artists play clubs in NYC all the time.

I would order Indian or Chinese or Thai food to be delivered in the middle of the night just because I could.

I would take in museums like MOMA, the Met, the Natural History Museum, or the Guggenheim.

I would eat a bagel. In NY, they taste different and better than anywhere else.

I would order a slice of pizza (cheese only to be a purist!) to eat while I walked through Times Square.

I would visit the New York Public Library, which is peerless.

I would shop (probably mostly looking) on Fifth Avenue.

Walk around Central Park one afternoon and ask where the ducks go in the winter.

Go to afternoon tea at one of the fancy hotels; the Lowell on the upper East Side was my most recent favorite.

If it’s mild out take a half-day tour on one of the open-top tour busses that go from the West Side.

Walk down Fifth Avenue from 59th to the New York Public Library at 42nd.

Go ice skating in Bryant Park or the Wollman Rink.

Get tickets to a play at the TKTS booth. I recommend “The Curious Incident of the Dog in the Nightime” or “A Gentlemen’s Guide to Murder.”

If it’s mild, take the Circle Line around Manhattan.

Have dim sum in Chinatown and dessert in Little Italy.

Play chess in Tompkins Park or Washington Square.

Walk around Macy’s – particularly the food floor.

Broadway, Broadway, Broadway

—Another vote for TKTS.
—Oyster Bar downstairs at Grand Central Terminal
—Use the subway, it’s the fastest and cheapest way to get around. Get a Metro Card at the first station from the vending machine. I’d put $10 on it to start (rides are $2.75 each)
—Take a round trip on the Staten Island Ferry (it’s free!). I timed to it watch the sunset and the nighttime skyline on the way back
—Take the subway to Brooklyn and walk back over the Brooklyn Bridge. In the morning the sun is at your back, shining on the skyline.
—If you see Gray’s Papaya or Papaya King GO IN THERE for a hot dog & juice
—As mentioned above, the main library at 5th Ave & 42nd St is beautiful, but if your are walking all day, ANY library is a great place to sit and rest for free

I enjoyed wandering around Greenwich Village. I liked going through Central Park. Loved going to see a Broadway show. We enjoyed taking the Staten Island ferry to watch the sunset too. Make sure you’re on the correct side of the ferry to take some photos of Manhatten with the sun going down. Be close to the front of the queue to get a good spot and sit outside. Have enough time to just walk around and soak up the atmosphere. There are a million things to do.

If the weather was above 50 and sunny I’d go to Liberty and Ellis island.

If you like art, the Metropolitan Museum of Art is a classic and you can pay less than the suggested price. Then walk around Central Park if the weather is good.

If you like to shop there is so much of it. You could go down to soho and see the smaller shops, or go to Bloomingdale’s or Macy’s. Macy’s famous Christmas windows usually are unveiled the beginning of November, you can find the exact date easily online.

What do you like? Food? Shopping? History? Theatre? Broadway is of course a NYC thing to do, but if you get Broadway tours in your town you might not want to pay the expense of Broadway. You might check out what is playing at Lincoln Center. An opera, symphony, or ballet if you like that sort of thing.

Have a pastrami on rye at Stage or Carnegie deli with a Dr. Brown’s cream soda. So many fabulous restaurants you might not want to eat deli.

Walk through Grand Central Terminal, which is featured in so many movies. The huge main room with the high ceiling and hustle bustle of people coming and going. The lower floor has a huge eatery if you want to grab fast food type lunch. Also, at Grand Central there is an annex to the Subway museum. Get a quick history of the subway and buy a souvenir.

Definitely go on tripadvisor. I always look at tripadvisor for ideas.

Since I’ve never been I’d firstly probably get lost lol, but I think I would like to go to the Broadway before I do anything else and then just explore.

The Guggenheim, tour Radio City Music Hall, see a Broadway musical and drama, Staten Island ferry, hang out in a pub, Empire State Building. Walk, walk, walk. Park Avenue, Broadway, Wall Street, Fifth Avenue.
I have been there twice and I nearly walked a pair of shoes off both times. There’s just so much to experience first hand. Avoid anything that requires long lines…life’s too short and there is too much to see in NYC!

Someone suggested the 911 memorial.

@rojo I’ve been to the 9/11 memorial and unless it has very special meaning to you, I wouldn’t spend the time it would take to go there. There’s so much life in NYC to explore!

^ I totally agree with @janbb. Only if it’s something you feel you need to see. I’d also suggest if you’re going to do that, that you go on a tour. You get through security quicker. Make sure you have somewhere to leave pen knives or anything else you can’t take in.

There’s so much to see and do in New York and your time is short. Do wear really comfy shoes and walk, walk, walk.

I live not far from NYC and I go there several times a year. I feel the best times on vacation are often the relaxing times, not the time running around.

Three nights – one night I would do a Broadway play, one night just strolling around Chinatown/Little Italy/Soho and one night probably relaxing at a nice restaurant and then strolling around some nice neighborhood (maybe the Village).

Two days – One day I’d pick a museum or two. There is a great one in the 90’s called The Cooper Hewitt. It’s a Smithsonian museum, small, intimate with great exhibits. I think one should be the Metropolitan Museum of Art. You could spend 5 days in the Met but you could also hustle and do it in one. It’s not far from the Cooper Hewitt.

Downtown there’s also the Forbes Museum. Last time I went there, about 10 years ago, I believe it was free. It’s a small museum but it’s great.

The second of the two days, I feel depends on what you’re into. Are you into history? You could do the NY Historical Society. Are you into shopping? One great store in NYC is ABC Carpet and Home. It is somewhat like a museum and you can hang out there and not buy anything, just walk on all the floors and look at furniture and all kinds of nice, beautiful stuff. If you’re into seeing some TV studios or TV shows, you should look in advance at seeing the taping of a show. That might be fun if you’re into it. If you’re into NYC stuff, there is, of course a ton of it. I agree with @Earthbound_Misfit that a tour would be a great way to see a lot of stuff in an efficient manner.

If you go to Chinatown for souvenirs or anything else for that matter, do not pay the price they are asking for their stuff. They expect that you might be bargaining with them. If they something is $25, offer them $15 and then settle on $20.

If you are feeling adventurous, take the subway to Brooklyn and go to the Brooklyn Museum of Art and/or the Brooklyn Botanical Garden. The Brooklyn Museum of Art is great and not your typical art museum.

@jca My sister and I used to like going to the ABC carpet store. That’s funny, I didn’t know it was a thing. We also used to like Poggenpohl to see all the pretty kitchens and fixtures.

Depending where the OP lives they already might live next to one of those stores, although with both some locations are much larger and grander. ABC carpet in NYC is much more of an experience than the Delray Beach location for instance.

I think Macy’s is more of a must see, just because of the history and size. Although, it is so chaotic in that store; so busy.

I third the tour suggestion, if it’s your first visit.
Although if you take some virtual tours online, you can probably pinpoint 10 times more stuff you want to see than you have time.

I took myself to Chicago once and came armed with nearly an inch of page printouts of things to see (this was nearly 15 years ago). I would map a course in the early morning and take off on foot with the appropriate sheets. Today I’d probably rent a mobile device two weeks prior to the trip so I could familiarize myself.

Your room is for sleep when you can go no longer. Watching TV while visiting NY is like reading a romance novel on the rim of the Grand Canyon. Sorry to say I missed most of the culinary delights because I wasn’t willing to slow down long enough for a real meal. Still, the street food is a wonder.

You know what? You just need to take me along, as a guide!

The free tour by Sandeman New Europe. They cover the most important sights and present history as a series of stories – amusing, shocking, or uplifting ones, but all of them interesting. Takes about three hours, and at the end, you tip the guide a sum you find appropriate.

I learned so much, it completely changed my opinion of city tours. Don’t miss it. I’ve been on about seven of their tours, and none of them were disappointing. Because it’s a walking tour, it’s a great way to start your visit, getting to know your way around.

Be careful to find the guys in red, with “Sandeman” written somewhere. There’s lots of copy-cats around.

Thanks to all who have answered. I am sure my wife and I will be using some of these suggestions come November!