Best hill town between Florence and Rome?

We had a car so I'm not sure about accessibility for all the towns we visited. The problem is the smaller towns you want to visit are less accessible. Besides Siena we visited Orvieto, Civita, Pienza, Pitigliano, Montalcino, and Montepulciano. My preference is in that order. Our favorite was Orvieto, although technically just outside of Tuscany. It has the added bonus of being on the train line to Rome, which would be convenient for you.

Hill towns are on hills and the train goes through the valleys. Besides Orvieto, which is not that small, Cortona is fairly accessible by train along the Florence to Rome corridor. The station is at Camucia, in the plain below, and from there it's a short bus ride up to Cortona. All of these towns are along the old rail line connecting Florence to Rome. Not the new high speed rail line.

Ella, from Rome to Florence, hilltowns can be found in both Umbria and Tuscany. In Umbria, two of the most popular are Orvieto and Assisi. In Tuscany, there are several. Cortona, San Gimignano, Montepulciano are somewhat close to the route. Note that of the five mentioned, only one has a train station (Orvieto). Assisi, Cortona and Montepulciano have train stations nearby and buses or taxis connect the train stations with the towns. For San Gimignano, as well as Montalcino, Volterra, Colle val d'Elsa, and some others in Tuscany, its a bus from Siena or Florence. They are a bit more difficult to get to without a rental car.

Look at Cortona. You take the train from Florence to Camucia, then either a taxi or bus up the hill to Cortona. RS has a walking tour in the Italy book. Also Orvieta is on the way to Rome. You just take the funicular up the hill to the town from the train station. I thought Cortona was less touristy, but may that's because we spent a week there.

We had a car and visited several hill towns. Orvieto was a favorite and easily accessible by train and then the funicular as mentioned. We spent two days in Orvieto and really enjoyed it.

Love both Orvieto and Cortona, but I would choose Orvieto for a stop on the way to Rome.

Thanks for all of the input! It seems like Orvieto is the easiest to stop at along the way by train. I guess we're going to have to make a second trip to Italy and rent a car to get the full Tuscan experience!

I have loved Orvieto on a couple of trips. From there, you also have the option of the local bus to the smaller hilltown of Civita di Bagnoregio (about 45 minutes each way).