I think this is a tough one because NY can be so different for each person. I've been there several times and each time has been so different. I think when you go the first time it's good to be a tourist, see the things you really want to see. I would suggest staying on Manhattan island and maybe spending less on tourist traps. For instance, you can go to time square and just walk around. You can do the same in Central Park and visit some of the famous department stores that border the south end. You can head down to the southern end and check out World Trade Center area, financial district, Battery Park (you can see the statue of liberty from there, it's a ways out, but you can see it) all with in a few blocks of each other. Chelsea Market is another good free thing to check out. From there you can head southeast and walk through meat packing district, Greewich Village (cool homes), SoHo (for the shops), Little Italy, China Town and wherever you want to go from there. That's a nice little walk. If you are active, I suggest just walking in certain areas. My wife and I would just walk around and get lost in Manhattan. It's safe just about everywhere so you really don't have to worry, even at night. So like I said, I'd rather be in the mix and pay a little extra just so that I can get out and walk. Besides paying for food, you could spend a ton of time there with out having to spend a penny for entertainment! I'm not expert, but if you have any questions let me know. My brother lives in the Lower East Side, so I can always ask him anything too!