When I retired from teaching on 2005, my wife and I took our first trip to Italy. We had six weeks, in April and May of 2006, and we decided to concentrate on Tuscany with a little bit of Umbria. We started out with a few days in Florence, which is a fantastic city, beautiful, walkable, with great museums and churches (and food and wine). Then we got a rental car and hit the countryside, staying at a variety of Agro Turismos (farms that function as Bed and Breakfasts).
The Chianti region was one of my favorites. Also Assisi, the many walled hill towns, and the spectacular village of Castelluccio among the Sibillini mountains in Umbria.
We had intended to do a fair amount of hiking, and our principal guide book was called something like "Hiking and Eating in Tuscany and Umbria," but we ended up doing more eating than hiking.
I would love to go back, next time probably in the fall. I'd also like to get to Venice, Rome, and Sicily some year, too.
-Eric
P,S, Some of my photos from the trip are on my website,
here and
here and
here.