Well, I've lived and worked in three of the most popular big-city destinations in the US (LA, SF, NY) so I definitely have an idea of what that is like; and I've seen my share of college towns as well. I really like Charlottesville a lot, but you really need to prepare yourelf in advance for what to expect. As a college town, Charlottesville really has everything...except for elite programs in sports that matter. For someone like me that really enjoys college sports, that's actually a pretty big factor, but at least they have Division I college football and basketball (and besides, I already have my team loyalties).
Charlottesville has a number of really good restaurants. I wasn't expecting much, thinking it would all be Applebee's and Hardee's, but I was actually pleasantly surprised. Now, you aren't going to find anything with Michelin stars there, so don't expect to dine out like you would in NY or SF, but I think the options are probably better than most cities below the Mason-Dixon line (to co-opt your geography), regardless of size, except for DC, New Orleans, maybe Atlanta. UVA being what it is, Charlottesville has quite a few truly relevant cultural attractions (as opposed to a lot of small towns that have stuff that nobody gives a cr@p about). Lot's of college towns have art gallaries and playhouses, but I think you'll find that those in Charlottesville are a cut above - and you have all the historically significant stuff as well (led by Monticello and the Univeristy itself).
A third big plus is the setting. It's a relaxed, country-club-like atmosphere around Darden and the University, and there are a whole bunch of golf courses within just a few miles ranging from moderate quality to pretty darn good. There are a lot of hiking trails and things like that as well; sure all colleges have things like these, but most can't match the overall setting that Charlottesville offers.
The night-life is where you'll really start to miss the big city (if you like that sort of thing). There are plenty of bars around, but most cater to the college crowd (obviously). You aren't gonig to find any warehouse sized clubs around Charlottesville. There's a wine growing region around Charlottesville, but if you're from SF and expect wines like those that you enjoy in Napa Valley, you're going to be disappointed. Obviously, Charlottesville isn't all that close to the beach, so folks used to the west side of LA will have to adjust. On the plus side, the co-ed population seems to be quite above average...I'm talking about academics of course
So, I'm actually very happy with Charlottesville. As a college town, it's pretty near perfect. You aren't going to find the hard-drinking that you will around some schools (we aren't in college anyways), and I've got to give a demerit for the crappiness of the football and basketball teams, but it's got quality in pretty much all the elements. If bonding with your fellow students and taking full advantage of what business school has to offer is a top priority for you, you will be ecstatic. Personally, I made the decision that hanging out with my friends from past lives wasn't the best use of my business school time and experience. If you want to be in a place where your friends will come visit you in school, NY, SF or LA are better choices. If you want to immerse yourself in the business school experience, you'll love Charlottesville.