Cortona

sure, you can see it in a few hours. It's not a very big town (but it has a lot of climbing). If you're driving you'll park on the road just before the actual town entrance.

Thank you Mike! Would you say that it's worth the visit? I'm just reading posts on a few other sites and some say that it's become very crowded and commercialized over the years. What's your opinion?

Becky we just got back from Italy and visited a lot of hills towns exploring shopping and eating. The two that I would recommend are Cortona and Volterra. Volterra is a short drive from Siena. I assume you are driving. So you may want to consider that as an option if you are mostly wanting a hill town experience. Assisi is a hill town itself. They experience an earth quake there in about 1998 and fixing the place as a result. Part of the fixing is cleaning and the color of the stones in the buildings really comes out as a result. If you have the time Cortona is great and you could certainly do Assisi and Cortona in a day.

We were in Cortona in October 2006. What a lovely City. Walked about 25 miles around the town..back and forth. You can actually see the house from Under The Tuscan Sun and see where they made the film. Don't miss this town.

We were there while they were shooting the film "Under the Tuscan Sun"....it was really amazing how they sprayed fake snow on the buildings and in the square to simulate the winter scenes in the movie (it was actually shot in October 2002). We stayed only one night in Cortona but really enjoyed it...we stayed in the Hotel San Michele, (great large room in old building) right off the square and ate dinner at the Osteria del Teatro...

I spent a week in Cortona last September. It is cute, low-key, & small, with a couple of interesting museums, good restaurants, and Santa Marguerita is worth visiting also. Lovely views from the hillside. It does get pretty much tourist trade because of the book/movie. It is somewhat commercialized because of this, but still very nice. I enjoyed hanging there for a week, probably more than I would just stopping by for a couple of hours -- but even doing that I would say it's worth it. Be sure to stop at the gelato store on the main street!

Google Eurobimbo (I can't remember the rest of the name of the website). Tania and her husband Keith moved to Cortona to live. Her blog covers Cortona and a lot of other things as well. We met them in 2005 and they had us over to eat when we were there in 2007. We too, were there when they were filming Under the Tuscan Sun. Last year it snowed while we were there so we got to see real snow in the square in Cortona!

Becky-
We just returned home from Italy this week and we stayed 4 nights in Cortona, using it as a home base for exploring the region. I've been to Siena, Volterra, Florence, Lucca, etc in the past and have enjoyed them but really loved Cortona as a home base. It's small, quaint, and great for relaxing at the end of the day. Parking was easy (just below the town- and free) and we even lucked out being there for a medieval ceremony honoring Santa Margherita which was followed up by an outdoor community theatre performance of Jesus Christ Superstar. I was worried when I had read some poor reviews on this site but I am scratching my head as to why someone wouldn't love this town. I found it to be one of least commercial of the "hill towns." I also agree with the writer that recommended Volterra. Also a great place to see.
BTW- Assisi was the one place we visited that was a zoo. I would get there early in the am or later in the evening.

We enjoyed Cortona on the daytrip that we did by car. There's an old Medici fort/castle above the town that we walked up to ("up" being the operative word in this steep village) and they were having a very cool exhibit of art throughout the small castle. Gorgeous views from up there. Like most of these Tuscan villages, it has its charm.