Thanks for the recs everyone, we had a great trip in Virginia. We stopped by Barboursville on the way to Charlottesville (from Shenandoah), it is a very beautiful place. We had the wine tasting and they do have some quality wines. We liked the most of them but we could only take one home because of the new TSA carry on rules. Overall it was a nice experience, the vibe was very different than the vibe we feel in the central coast of CA.
I agree with the White Hall recommendation. I also agree that part of the Virginia wine experience is being at the vineyard and the beautiful surrounding countryside. And fall is the best time for that visit.
Jefferson Vineyards is also a nice visit and very close to Monticello and Ashlawn Highland (James Madison's home)if you have an inclination to visit a couple of historic homes while you're here. King Family Vineyards in Crozet is in a beautiful setting as well and frequently has polo occurring on the grounds.
Charlottesville is pretty casual dining wise, so you should be fine with jeans and nice shirts. A few recommendations are:
Duners (American; west of town in Ivy, convenient if you go to White Hall or King Family);
Starr Hill (local brewery if you want to keep the tasting theme) or Continental Divide (southwestern) on West Main Street
Mas (tapas) in Belmont
Blue Light Grill (seafood) or Zocalo (southwestern influence) on the Downtown Mall. If you go to the Downtown Mall, try Splendora's for some gelato after dinner.
Barboursville wines are nice and the vineyard is lovely. Whitehall also has some good offerings and Veritas's viogner is pleasant. In my experience, Virginia wine tastes best in Virginia. I.e. whenever I've tried to give it as a gift, the recipient is usually a little ho-hum about it. What's good about the wine, I guess, is in part the experience of buying it. If you go to White Hall you can also visit Our Lady of the Angels Monstery where you can buy the gouda they make on premises (can't view the cheese making, though-- health dept. regulations). It's delicious. The place is hard to find (it's technically in Crozet) but their number is listed online. I hope you haven't already gone to Cville-- if not, let me know if you'll be in town for lunch or dinner and I can give recs...