Philly is nice and has its own charm, but for someone like myself from Canada, it was a hard adjustment. Over time I grew to really enjoy Philadelphia and the people at Penn.
Downtown philly is a short bus ride away (15 mins), or a $12 cab, lots of great bars, lots of students in Philly (second most students / capita only after boston), lots of great restaurants that were affordable! Penn's campus is next door to the dental school and there are lots of activities to go with that, and lots of get togethers with other grad schools and free booze/parties (boat parties, wine walks, dinner cruises, etc) all subsidized heavily from their 6 billion dollar endowment.
I learned a lot from some amazing faculty, but of course, there were bad faculty as well, that made me stressed and angry - that is dental school anywhere. Penn helped me specialize... that was high on my priority list. They inflate grades, and (sadly) grades are king when applying to residencies. You'll be around a lot of like-minded, well-driven individuals at Penn and that will make a big impact on your education. We got 2 months off the first 2 summers, and 1 month off for the last summer.. those were nice breaks.
It sounds like UCSF may be cheaper though... unless you get one of the Dean's scholarships at Penn. I don't know much more about UCSF. Both are great options in my opinion. I would love to have lived in California, you can't beat that.