My favorite place to go (by far) was Central Park. There's always a ton of people there and it really is a nice break-away from reality. [http://www.centralparknyc.org/visit/things-to-see/index.jsp?page=1 | Conservatory Water, Alice, Balto, Bethesda Fountain/Terrace, Cedar Hill, Great Lawn, East Meadow]
Being a boater, my 2nd favorite thing to do in NYC was ride the Staten Island Ferry - it's actually a free ride too (or at least it was when I was there -- I looked it up for you, and yes, it is still free). I literally would ride the Ferry back & forth just simply to get on the water and feel the cool breeze (it also didn't hurt that you get pretty close to the Statue of Liberty, so you get to check that out when most of those "Tours" to do the same thing are ungodly overpriced and horrendous long hour waits.
Another "free" thing to do is to go to NYC Metropolitan Museum of Art. Perhaps the best kept secret is that the Met is actually "free." Yes, free. They advertise ridiculous admission prices, but if you look closely, they are entirely recommended prices. Because the Met is funded by the state, you can technically pay whatever you want to get in. So... technically you can "donate" $5 and receive admission as opposed to spending the recommended $25 admission fee.
It's not "free," but I do recommend going to the top of the Empire State Building. Why? Because you really do get a great view (especially on a clear day) of the entire NYC skyline. Don't fall for those guys advertising that you can "skip the long line" and "take a helicopter ride." You don't want to do that. Bide your time and you will be up to the top in no time. Besides... once you get up there, you want to take your time and take in all the sights. You do not want to be rushed or scooted out of there because it's time for the helicopter to grab a new set of tours, right? (NOTE: At the time I was in NYC, the World Trade Center Memorial was in it's infancy. There was really nothing to see. The fences 15 ft high and you really couldn't see anything (at least worth-while). By now, things have likely changed, so it might be worth-while to swing by over there and check out what the Memorial has to offer.)
I know this one is going to sound stupid / cheesy, but... seriously... ride the NYC subway. It smells and it's dirty, and you'll see some interesting characters, but really... it builds character. I promise you will come away with a deep appreciation for just how spectacular the NYC subway system truly is, and how impressive the whole "underground" (under the city and all it's buildings) truly is. (It's also a great way -- perhaps even the best, in terms of cheapest -- way to get around the city. Sure cabs are faster, but you will end up paying MUCH more if you rely on cabs, as opposed to learning & getting around the subways.
If you have even the SLIGHTEST sweet tooth, you MUST go to Magnolia Bakery. I PROMISE you they will have the best tasting cupcakes you have ever had in the world (or at least that I've had). They are a little pricey (I wanna say $4 per cupcake or so; but that's because they are THAT good and it is a famous bakery), but the frosting is simply to die for. You might ride a sugar buzz the rest of the day, but I promise you it will be worth every penny for those 5 minutes of indulging in it.
One of my favorite restaurants that we went to (granted it has sentimental value) was La Caverna. It's a little pricey, but it has a really great ambiance and some pretty tasty good food.
A nice "snack" and something that is definitely cheap & affordable, yet EXTREMELY delicious is Pommes Frites' fries & sauces. I kid you not, you are going to think, "What can be so special about fries?" but trust me... go there and you will see. They literally have EVERY kind of sauce you can imagine and it's a nice "break" / snack to stop and eat some delicious fries with amazing sauces. It's right in the middle of Hippy Town/Village, so it would be a great excuse to see some of the culture NYC has to provide. DEFINITELY recommend this place.
I know it's going to sound cheesy, but seriously... take one night and go see Times Square. It kinda is impressive and just a fun / touristy thing to do. Again... it won't cost you any money other than the transportation to get there. I would recommend doing this at night so you can see all of the bright lights. It truly is breathtaking (at least for me it was).
Finally, I never saw a Broadway show (and like I said, I spent an entire summer living in NYC), but I really wish I would have. This is definitely one thing I truly regret. I wish I would have just forked out the money and gone-and-seen one. Not quite sure what's playing out there now, but I definitely wish I would have caught the Lion King (or even Phantom of the Opera, again) out there.
Other "cool" things to check out...
- Grand Central Terminal (touristy / people)
- Madison & Fifth Avenue (shopping)
- Museum of Sex (vogue / interesting)
- Brooklyn Bridge (touristy)
- SHARK Speedboat Thrill Ride (tour)
- Chinatown (NYC) (funny / edgy)
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