Tuscany

I am going to suggest something a little different than most will suggest here: Gubbio. Gubbio is a hill town in Umbria, and well worth the treck if you have a car. It is quite Medieval; it does not look much different than it did 700 years ago. You can eat at the Taverna Del Lupo, one of the best restaurants in Italy, and explore the pottery, cheese, and wine shops in the area. Look for the "Doors of the Dead"--in the Middle Ages, it is rumored that when a member of the household died, they would place their bodies on the steps in front of this door for the townspeople to pay their last respects. It's quaint and untouched by tourists with a fascinating history. At the top of the mountain where the town sits, visit the church of St. Ubaldo, and see the perfectly preserved saint (dead for a 1,000 years) in a glass casket on the altar. Happy travels!

richard,
See http://www.slowtrav.com/italy/tuscany/hs_planning.htm

Perugia is sadly neglected and a great place to spend several days with a few expeditions to the smaller towns.