I highly recommend the tours at Monticello. On our recent visit the guide was fabulous – engaging and poignant and obviously a scholar and admirer of Thomas Jefferson. We were almost crying at the end of the tour. The tour guides do an excellent job of presenting the environment in which Jefferson and other southern landowners lived and the contradictions and nuances of the institution of slavery in the south.
The countryside around Monticello is lovely especially in this fall season and there are so many interesting stops in close proximity. After visiting Monticello, we continued on down the road a few miles on Route 53 to Jefferson Vineyards for a short picnic, then on a few miles more to Ash Lawn, President James Monroe’s home (he used to visit Jefferson by horseback), and then just a few miles further to Trump Winery to see what the new Trump owners have done to the beautiful former John Kluge Estate. The wine is not very good (our opinion only…) but the setting and the tasting area is lovely. We did not get a chance to visit Dave Matthews' (yes the singer) vineyard - Bleinheim Vineyard - right around the corner. Next time.
For dinner - Hamiltons' on the Mall in downtown Charlottesville is excellent. The menu changes often to take advantage of fresh and seasonal ingredients. My blue-plate vegetarian plate was perfect. (I feel that any restaurant that can do a tasty and elegant vegetarian entrée definitely has a leg up on competitors.) The crab cakes with pickled okra and crispy bell pepper polenta was memorable. And Charlottesville’s downtown pedestrian mall is quaint, charming, lively and fun with cute boutiques and shops.