New York is one of those places you can visit every year, and find something new and interesting to do every time you go. To me, it seems like I get more bang for my buck in New York than almost any other place, because the city is jam packed with fun.
Of course, if you’re headed to New York, you want to see the regular travel guide book stuff like the Empire State Building (preferably with your sweetie), Ellis Island, The Statue of Liberty, the Met, the Guggenheim, Ground Zero, and eat a New York Street Dog, but I think one of the best ways to experience New York is to let things in New York find you.
My favorite way to travel to New York is on a short vacation, and not to make any actual plans beforehand. I know that sounds kinda nutty, but there is so much to do in New York, each time you go, you will experience something new and interesting.
There are so many great restaurants in NYC (both hole-in-the-wall, and fancy), so just stumble in one whenever you get hungry. Check the local guides for what art exhibits are happening where, and check it out whatever sounds interesting. Also, check out what is happening in Soho, Chelsea and other fun districts. Walk down the streets of Chinatown, Little Italy, or Russian-themed Brighton beach, and get some culture. Show up at the TXTS booth and get tickets to whatever show is on sale. Pick out what kind of dancing sounds fun, and then find any club that matches your groove for the night. Really, you can’t go wrong.
The only thing I would say to plan on is a place to stay and transportation schedules. Hotels/hostels book up fast, and there are rats on the street at night, so sleeping on the streets is gonna bum you out if you don’t plan in advance. Also, figure out when the subway runs. The last thing you want to do is be stuck somewhere expecting to take the subway, only to find yourself gated out of the station. I’ve experienced that, and it’s not fun.