@prncss47: I’ve lived in both NYC and Boston, so I have some tips if you want to avoid the traditionally touristy places:
Mustang Grill – I believe Derek Jeter is part-owner of this place. It’s a great bar on the UES. Yummy margaritas and fun decor.
Banc Cafe – This is in Kip’s Bay/Murray Hill. Beautiful new American bar/restaurant. One of my favorites.
Peacefood Cafe – This is a vegan restaurant on the UWS. I am NOT a vegan by any means, but my vegan friend took me here once, and each time we hang out, I beg her to take me here b/c it’s SO good. The not-chicken bucket tastes like actual good chicken… and ::mind blown:: it’s not chicken.
Josie’s – This is an organic food restaurant on the UWS. Everything is not only super healthy, but it’s YUMMY. I love their bloody Marys. I had a birthday dinner here.
Amber – This is on the UES, I believe. It’s a nice sushi restaurant – very good drinks and yummy sushi. A little pricey, but worth going to once.
Perfect Pint – If you are looking for a pub-type bar, this one is great. I am only speaking for Midtown East though (there is another one Midtown West). Very standard albeit yummy pub fare and lots of beer on tap.
Cheers – This is a classic favorite. However, the one at Faneuil Hall is a replica. The original one is on Beacon Street.
Border Cafe – Really fun Mexican restaurant at Harvard Square. Colorful decor and HUGE margaritas.
TASCA Tapas Bar – A little out of the city, but you can take the B line directly there or walk using the C line. This is a great Tapas bar that I actually used to live next door to. It was always a popular spot, but sadly, I waited until the week I was moving to actually go there.
I don’t have that many for Boston b/c I moved out of there in 2007 so I bet many of the places I used to go to are closed or chains now.