I am from the Charlottesville area- the road that Monticello is on has lots of cool things to see, and the road is nice and windy (but a little slow). Stop at Carter's Mtn, the road up it is rough (but I have done it in lowered cars several times), and the view is AMAZING of Cville. Plus you can pick apples.
Stop at Michie Tavern- fun little shop with tons of random stuff, and the building itself is very old and cool. Lots of vineyards in the area for sure.
Go into downtown Charlottesville/UVA area- cool old buildings, lots of younger people, and great food. Charlottesville definitely has a huge selection of local food that I miss, a lot.
If you want to do a romantic Italian dinner, go to Vivace. My favorite place in the worldddd
Someone mentioned RTE.33- definitely go on it. Skyline drive is gorgeous, but is very heavily trafficked especially in the fall, so get on rte.33 as it's two lanes up and a really really fun drive.
If you have any more questions about things to do/see in Charlottesville let me know, I'm happy to help.