IMO,

Best food in the city is at Alinea. Probably best food in the country (ranked the highest at least). Good luck getting a table.

2nd best food is at Girl and the Goat. It was just awesome. I was able to buy a house faster than I was able to get a table at G&G but I heard its possible to walk in if you are willing to wait some. Price was about 20% of Alinea.

Definitely go to the terrace at Trump. Its an awesome place to get drinks and is the perfect anniversary spot. Views are fantastic.

What weekend are you staying. Your prices sound outrageous. For $500 you should be able to get Park Hyatt, Peninsula, or Trump. I hear Elysian is the new place to beat.