How many hill towns can we see in 5 days??

As with many things in Italy, it depends. Have you ed a town to base yourselves in? Are you focusing on Tuscany or Umbria or ???? I would recommend one town as a base, giving you 4 full days to see other locations (discounting arrival and departure days). You can perhaps the town where you will sleep based on what towns you want to see and what you want to do. Hiking? Art and history? Wine? What do you want to do when you get out of the car? Also, what is your tolerance for car time? Two or three per day, to me, means hop out, walk around for 30 minutes or an hour, then back in the car. Not really time to "do" anything. The towns may look close, but driving times are sometimes slow because of twisty, scenic roads. All that said, if you plot the towns you wnat to see on a map, a more-or-less central location should emerge and that may be a good base for you. The Slow Travel webiste has some excellent ideas for driving tours on this page if you look at the nav bar on the right you'll find many ideas for drivign tours.

I agree with Laurel about getting a central location to stay in. You can drive out to many, many towns and have a relaxing vacation. 2 towns a day is a decent pace. We did this in March, 2012, and had a wonderful time. Our favorite hill towns were Volterra and Orvieto.

Ditto....it depends. Some hill towns could be a full day to really enjoy it. Urbino is pretty big and worth the full day. Vinci is very tiny and worth a half day at most. As Laurel said, the driving times are probably gonna be more than what you expect and add in that in June you're sure to run into groups of bikes on those small twisty mountain roads. I'd say plan on two at the most and then squeeze in another if possible.

I agree with the others. Three towns a day is definitely too much. I would plan for 2 max but even then, I regret splitting 2 of our days in Tuscany between 2 towns each day. We visited Volterra and San Gimignano in one day and regretted not spending more time in Volterra. We also visited Montepulciano & Pienza in the same day and to be honest, I would have preferred a slower pace. While Tuscany seems very compact, it does take time to drive from town to town and what took a while was finding parking, figuring out how to pay for the parking (in some towns) and then walking into the town, etc. In several towns, we drove around for a while trying to find public parking. We used a GPS, but the GPS didn't steer us to the parking lots. This took more time than I had anticipated. Because we saw 2 towns in one day, I felt like I didn't get to really saturate each town, walk around & take it the ambience because we were rushed to get to the next town and then to get back to our agriturismo before dinner. If you visit Orvieto, Siena and/or Volterra, I would definitely devote a full day to each. Enjoy Tuscany!

Brendon, if you are determined to visit two or three towns in one day, you can combine a larger one (like Arezzo) with one or even two smaller ones (like Sansepolcro). Another combination would be Assisi and Spello (only about 7km apart). I was traveling with friends last year and we sometimes managed three towns in one day, but we always made the third choice an "optional" one in case we didn't get to it. We based in Siena (at Hotel Minerva, has an onsite parking garage and is just outside the city gates, so no ZTL issues) for Tuscany, and since we had 10 days, used Assisi as a second base (for Umbria).