Visit the Cloisters
The Cloisters are run by the MET and therefore are by donation only. Our friend who lives in NYC says the MET has enough money, so we paid $5 per couple :) There are beautiful gardens, free tours every half hour, and lots of gorgeous art! Almost the entire thing has been pieced together by the Rockefeller family from monasteries or castles in Europe. It has such interesting history and is a great reprieve from the city if you feel like you need to "escape". More info here.
Be Part of a Live Studio Audience
There are SO many opportunities to be a part of a studio audience in NYC -- we were able to be on the Daily Show with Trevor Noah which was so fun! Many of these are based on a raffle, so you don't have a ton of choice in your date, but it could be a fun thing to plan your New York trip around.
Check Out the Local Events
The NYC Parks website has SO much great information on free/cheap events going on in the city. I'd check it out. I found so many different things to do when we were in New York in July, although it would be quite different in the winter. I did Broadway in the Park, attended workout classes, movies on rooftops, and live music all over the city! The city does a great job of hosting these events, you just have to see what's happening.
Roosevelt Island Tram
The Roosevelt Island Tram is so fun! Roosevelt Island is in between Manhattan & Queens that just has some housing and parks. It's really cute and feels removed from the city somehow. You can take a subway train there (only one line stops there) OR you could take this fun tram! It's like a gondola you'd take up to go snowboarding. It gives you a great view of the river and 3 boros. You pay with your MTA ticket, so it costs no more than a subway ride (or is free if you have a week/month pass).
There are so many gorgeous rooftop bars. We loved finding rooftop spots at sunset to catch views like this one! Find a list of rooftop bars here. The photo below was taken at Roof at Park South in Kip's Bay/Gramercy Park.
Pizza by the Slice
As if you needed an excuse? Pick up some pizza by the slice for a cheap dinner on the go. It was something we liked to do if we wanted to eat in the park or on the water. Joe's Pizza is one of the best and is easily located in the East Village at 14th St E & 3rd Avenue, or Greenwich Village on Carmine St. & 6th Avenue. PS - I absolutely love the East Village AND Greenwich/West Village. Two of my favorite areas in Manhattan!
If you want to visit Governor's Island I hope you've been saving up.... it's $2 round trip and you have to pay up front :) The ferry ride is short and leave every 30 minutes. It provides great views of the city and is a great place to spend the day outside! You can take long walks, enjoy the fun slides and hammocks, or rent bikes. There's also some fun art and cute food trucks. We brought a picnic and some wine and made an afternoon of it. I loved it and would highly suggest it if you're visiting with good weather.
Talk about cheap thrills - Coney Island is #1 on this list! You can take the subway out there, and then you don't have to spend any money if you don't want to. Matt wanted to try a Nathan's Hot Dog (this is where they do the hot dog eating contest every year) so we spent a few bucks. :) It's got an old carnival feel but is a lot of fun.
There are several ways to see broadway shows on the cheap or even for free. You can sign up each day to win a number of raffles (almost every show does it, but each show has different rules, so check with them directly) and I've had a lot of friends win these free tickets! The thing is they are for that day only, so make sure you're free. Or you can often find severely discounted tickets day of but in limited quantity. Another great way to get tickets around $25-50 is downloading the TODAY TIX app. We saw Curious Incident of the Dog in the Nighttime AND Les Miserables for $29pp. Yes, we sat in the back row but it was awesome and saved us a TON! Sign up using my link and take $10 off your first show!
Brooklyn Brewery Tour
They only offer tours on the weekends as far as I know, but it's a lot of fun and it's free. I'd suggest going early as they fill up quickly! They also have a tasting room with pretty cheap beers and some of these brews are harder to find so it can be a bit of a treat!
What are your favorite freebies in NYC?