If you will be hitting the city, the North End has about 50 or so italian restaurants to choose from. Yes, 50! There are other respectable establishments near Quincy Market. My favorite in that area would be The Union Oyester House. It looks like crap but it is over 200 years old. Pretty good seafood there.
For bars, if you're looking for something that could turn into porn, you may want to try Aqua which is off of Broad Street behind Quincy Market heading toward the financial district. There is also The Rack, a combo pool joint/pick up joint right next to Quincy Market. Otherwise there are so many places to choose from in that area it is difficult to pick one out.
The North End is within walking distance of all of the other places I mentioned.
For a quick sight-seeing, the U.S.S. Constitution in Charlestown is a nice visit. It is the oldest commission warship in the U.S. Fleet. Has a nice museum and a few WWII ships anchored there also for touring. Have fun.
Mr. I.