Subject: R: Hill Towns
There are plenty of hill towns to see between Florence and Rome. Coming up from Rome there Umbria with Assisi, Perugia, Todi, Spello, Gubbio. Then, you'll find Cortona, and the places Don and Linda describe in their travelogue. Then, Montalcino, until you find Siena and San Gimignano.

If you don't want to consider big and/or inflationed towns, well, the choice is among Todi, Spello, Gubbio, Cortona, and Montalcino (and the places in the travelogue).

As regards the Chianti area: Castelnuovo Berardenga, Radda, and Greve in Chianti are to be recommended.