I went to college 50 minutes west of Boston and have been there more times than I can remember (maybe the parties at my friends' in Back Bay didn't help).
Anyway, the one touristy thing I do recommend is the
Duck Tours. It's a great way to see the city and have fun. It can be a little hokie with the whole "quack quack" thing but you're there to have fun.
A couple of my favorite places for food and drink is sitting at the oyster bar at Union Oyster House (and getting oysters and clams shucked right in front of you....don't bother with the dining room). I also love The Daily Catch on Hanover St. in the North End for calamari or steamed mussels. That place is the size of my cubicle. Lastly, I can't forget Boston Beer Works across from Fenway on Brookline Ave. or on Canal St. near North Station. Love thier sour cream and chive fries.