Boston is like my adopted second home. A great place to visit even in the winter time. If you are there during New Years, definitely attend First Night activities, but don't forget your mittens.
I was in Boston last week for business. First time I've been there, and I really enjoyed it. I'd like to go back some time on a personal vacation. My Dad used to live in Chicago, and I visited him a few times. I can't imagine ever going back there unless I had to.
I just picked up my tickets for the game in Chicago on December 4th. Found pretty sweet seats on Craiglist from a season ticket holder...right next to the visitor (Rockets) bench and tunnel...should be good. Look out for the two loons wearing red and gold Maxwell and Olajuwon jerseys. :grin:
It is already cold here in Chicago (I walked to work on Friday morning and it was 31 degrees) and its only late Oct/early November... and yes, i had to throw away my umbrella that lasted me 10 years in Houston last week because the wind destroyed it. December/January/Feb are gonna be brutal.