Boston sucks. It is fun to visit occasionally, but after 24 hours I have had more than enough. Boston has the European feel in that it is always under construction and you can't understand what anyone is saying.
I would pick San Diego hands down, even if it is in the Союз Калифорнийский Социалистических Республик (Union of Californian Socialist Republics). At least they have nice weather.
-J.