for bars, in Faniel Hall there are a ton to bar hop. The Black Rose, The Bell in Hand, The Place, The Tap. walk 2 feet and you'll run into another bar in Faniel Hall. if you head over to Boylston St. check out the Catus Club and get a Sand Bowl, check out the Poor House, Wiskey's, and if you have a craving for a cigar go to Cigar Masters. If you go to hang out in Fenway hit Lancedown St. right across from Fenway Park. there is a row of bars and clubs. Jillians is usually a lot of fun.
As for sight seeing, you have to take a Duck Tour of Boston. you can check out the MFA for art, Symphony Hall.