I love Boston. I can't help it. I LOVE Boston.
I was born and raised on Cape Cod, and I went to college at New York University and Boston University. I love both cities, actually. But Boston feels more like home to me.
I guess the question is - what are you looking for in a city? Where do you live now? How able are you to handle cold winters? Do you like sports? Do you like people who like sports? Are you able to drive like you're in a war where using your directional is seen as a sign of weakness?
Boston is a MAJOR college town. But not in the sense that other places are college "towns." It's not a bunch of jackass hipsters. It's a LOT of really smart, really diverse, really interesting people. Cambridge and Somerville are awesome too, just outside the city. There are great places to shop, great veg*n places to eat, great music, great art, great sports, great educational opportunities, great LOTS of things.
But heaven help you if you think there will be bountiful street signs. The roads are set up in an "If you don't already know where you're going, you can just get the hell out" kinda way. Part of it they can't help - it's an OLD city so a lot of the roads used to be, I dunno, cow paths. So they kind of wander and cross over each other.
(You get used to it, I promise.)