One of the best times in NYC was a school trip I took with my son's theater class in 2010. The trip on a whole sucked but there were a few bright spots. Mainly getting to spend quality time with my son before he left for college in the fall. First off, high school kids are obnoxious. Especially 6 of the kids in this group of 8. My son excepted. The teacher did a crap job of planning the trip and it was extremely low budget due to her bad planning and miscalculations. However, it is possible to have a good time in NYC with very little money.
You can get the best pizza for cheap in NYC on just about any corner. I know places where you can get a bacon, egg and cheese on a roll for a couple of bucks. Dirty water dogs will do in a pinch but why when there's Papaya Dog. Big soft pretzels from the street cart are the best. Gotta have a Pepsi to go with. And of course there is Mr. Softee ice cream. I can make a meal out of Pommes Frites any day. My fave sauces are smoked eggplant and Mango chutney. I've heard the Poutine is to die for but... literally. It's all cheese and gravy and fat on top of french fries which is probably why it tastes so good. But I just haven't been brave enough yet. Chinatown has many terrific and authentic eateries. I like 27 Sunshine. It would have been fun to take the kids to someplace like the Stage Deli or Katz's where they filmed a scene from "When Harry Met Sally." But the teacher made arrangements for Dallas BBQ. Because being from North Carolina, it makes sense to take theater kids who have never been to NYC before to go get Texas BBQ while in NYC. It would have been nice to have one special dinner at someplace famously cool like Balthazar but the teacher made reservations at Alice's Tea Cup instead. It is a nice place in and of itself. No disrespect. But my NYC born and raised 12 year old niece said it was a great place to go "when she was a little girl." The 3 high school guys in the group weren't so impressed either.
I did my best to salvage the trip and provide cool, cheap, New York-y things to do. The High Line is a great place to go and chill out. A respite in the middle of the city. Central Park is great too. From Turtle Pond to Belvedere Castle to the many bridges, statues and landmarks all over Central Park. It is much bigger than you'd think it is. Most museums have a free day once a week. Sometimes they'll accept a "donation" if you show up with 9 kids and plead poverty. There are free, impromptu shows going on all over the place. Union Square, South Street Seaport.... We took a ride on the Staten Island Ferry. 2 of the other 6 kids joined us and they said it was awesome. The weather was great. We got to sail around and see the Statue of Liberty. The other kids and the teacher stayed back and waited for us in Battery Park. We had a great time. Their loss.
On one of the last nights of the trip we had a little money left and the teacher gave us a choice to spend it or save it. On one last ditch effort to get the kids to one special touristy NY thing, I tried to convince the kids that the $20 to go to the top of the Empire State building would be worth it. The other 8 kids and the teacher decided to go to a free program. My son and I decided to go to the top of the Empire State building. It was an hour before sunset so we got up to the top and it was still light. It was so hot that day but at the top of the Empire State building there was a welcome breeze. It was crowded but my son and I managed to find a spot where we could see all the way to Long Island to where we used to live. Then the sun started going down. As an added bonus we got to watch the sun set from the top of the Empire State Building. We watched as the wave of darkness rolled from one neighborhood to another. Replacing bright, twinkling lights in its wake until the entire City was lit up for the night. It was one of the coolest things that I have ever seen. I highly recommend it. The best $40 I ever spent.
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