i'm a bit biased b/c i've spent my whole life (minus 4 yrs of college) in south florida and it gets old very quickly... driving everywhere, traffic, rude people, feeling like you're in another country, fast-paced, no seasons, etc etc. it becomes stressful.
i've been to boston a number of times and it is by far my favorite large city in the entire country. very historical, tons of college kids, beautiful (17th century buildings), possible to live car-free, SEASONS, close to the mountains (i love to board), and i could go on & on....
with that said, i've never spent any considerable amount of time battling a brutle winter so take what ive said with caution.
jb!🙂