That's where my whole family is from....you are gonna have an amazing time! The best accents in the world IMO!! I will find out from my cousin what's hot and get back ta ya! He works at some pub near the Ma'kit! Have a great time....I can't wait to have my family reunion there in June!
Its not much fun in terms of night life but is a great place to chill, relax and wander around- there's lots of beautiful places to visit and the restaurants are phenomenal (if a little pricy).
Quincy Market is worth checking out (makes St. Lawrence look like crap) as is MIT, and the aquarium. If you're into cheesy pop culture there's always Cheers. In terms of clubs and stuff, you're probably better off finding some bar and drinking until you're kicked out at 2 am.
i ditto everything else that's been said. boston is a beautiful city with so much history ...i absolutely love it. the nightlife is kind of ass but there are some things there, you have to look really hard for it.
p.s if you're going to be doing any recreational substances, be prepared to buy more than you would usually buy. last time i was there, i noticed i had to take 2x what i would normally take.