Umbria

Gubbio was one of my favorite spots on a recent driving trip.

In addition to Gubbio, Assisi, Montefalco, Trevi, Spello. What time of year are you planning to go? Transportation means?

On the border of Tuscany and Umbria, and close to Assisi, I love Cortona. Don't pass up this quaint hilltown if you're in the area. A wonderful Etruscan museum, the Diocesan Museum of Cortona that contains a collection of works by Signorelli, beautiful Duomos (although some are quite a hike uphill), and a flat, easy to walk main street with wonderful piazzas were all a delight for me to discover. Enjoy!

I'd suggestion having a look at a guidebook to determine which places interest you the most. After that you can work out how to get to each of them.

Orvieto is one of the best places to visit (IMO), and has some interesting sights. Assisi is also worth a stop.

We spent some time in Perugia. It has excellent transportation connections and we visited Spoleto, Assisi, and Gubbio on 3 day trips. The TI in Perugia was very helpful, suggesting sights to visit as well as the best transportation--bus or train--to each town. The minimetro is a great way to get back and forth from town to train/bus station. We liked our stay at the modest San Ercolano Hotel...friendly, comfy, nice people and nice little breakfast. And very close to the minimetro we used daily. Safe travels.