Hill Towns

With a car, I'd make it Perugia since it has merit on its own. You could scurry about to the usual suspects in the oft-debated popular hill towns in one day, get that out of your system, then poke around Umbria which is largely neglected.

There is Siena, San Gimignano, Volterra, Cortona, Montepulciano, also.

Not much to see in Pisa I'm afraid.

Jo,
This may help http://www.slowtrav.com/italy/tuscany/hs_planning.htm

I almost always agree with Ed but we tried using Perugia as a base and it didn't work so well for us. It was a challenge to easily get in and out of the city (lots of traffic), we had some disappointing dining experiences, and just weren't that thrilled with the town in general. We enjoyed Montepulciano as a base for visiting hill towns in Tuscany.

Hi Jo - My friends Berta and her husband Andrea have a Beautiful B&B just outside of San Gimignano and very close to Siena, Volterra, and even Florence. Please check out their website.
http://www.casolarelibbiano.it/

Ciao, Greg

We stayed in Perugia, up in the hill part of town (there's a lot at the base) and parked the car on streets approaching the top of the hill. Did the same in Cortona. We've also stayed in Spello and parked the car in the hilltown at the hotel (you'll want a SMALL car to do that!). I thought Perugia was fine, especially the large center piazza and restaurants around it.

Here's what I suggest. If you're looking to visit specific hilltowns such as Assisi then pick a place to stay near it (Perugia is the next town over), otherwise pretty much any will do. Spoleto, Spello, Cortona, Perugia, etc. You don't even really need specific plans for where to go on your day trips; we'd look at a map, say "lets go here today" and off we'd be. Once there we'd go in the afternoon to another one in the vicinity. One thing we liked about Perugia is there is a car rental place affiliated with Auto Europe right at the train station, so we took the train from Rome and picked the car up easily. If you're getting a car then I would strongly suggest bringing a portable GPS.

If you want to explore Tuscan hill towns, somewhere near Siena would be a good home base. Also good for exploring the Chianti region. If you want to explore hill towns in Umbria and Le Marche, somewhere near Perugia would be good. I found Assisi to be a good home base for that area. Orvieto is a great town, but a bit south for a good home base.

Enjoyed 3 nights in Cortona with no fixed agenda. The pension we were at was outstanding and each day after an amazing breakfast, we would point the car toward a new location or simply enjoy Cortona itself. Montepulciano was a great little trip with lots of wine sampling.