Things to do: Monticello is a should do, as is a walk around UVA's campus, er grounds, downtown mall is fine but shops are expensive for what they are (shopping is not good around here). The Culbreth Theater at UVA and the Live Arts theater downtown offer good theater, so if you're looking to take in a play after dinner, check out both of them. There is occasional live music at a few venues. And there are movie theaters on the west end of the mall. The 1 vineyard I'd visit is Barboursville. They have a decent tour, and they're 1 of the very few VA vineyards with decent reds. And it's located on the ruins of former Gov Barbour's grounds, where they have outdoor plays in the summer.
Food: There are many upscale restaurants, most of which I consider to be overpriced. If you're staying down in Nelson Co, there are 3 nice breweries down there. In town, the 2 "nice" places I recommend are Fellini's and C&O (entrees in high teens to low $20s). They're on opposite ends just off the mall - C&O is kinda creative continental, and Fellini's is the only Italian place in town that I like (C&O has a quiet and romantic atmosphere, whereas Fellini's has music most nights). I ate at Peter Chang's last week for the 1st time, and the food was great - authentic Chinese cuisine. A friend who is Chinese and who is a foodie says it can be very good some nights and so-so on other nights depending on who is in the kitchen. I would do a cheap lunch on the downtown mall 1 day. I love Christian's Pizza and the dumpling place that is 2 doors down. Bodo's has good bagels for breakfast.
Some good tags here.
