For once, we will try to be brief: first, put Florence to one side as an issue. If your goal is to visit charming Italian hilltowns, does it matter where, specifically, you base yourself?
Our answer is, overwhelmingly, NO!!! To us, it doesn’t matter whether you put yourself near Todi or near Lucca or near Orvieto or near Siena: Either you’ll visit these 10 hilltowns or you’ll visit those 10 hilltowns. As far as we’re concerned, it hardly matters which 10 you end up visiting. If you’re near Orvieto, you can’t comfortably visit Lucca. But you can go to Todi, to Viterbo, to Siena, to Spoleto, to Assisi, to Perugia, to Montepulciano. And that’s just a beginning. What does it matter if you can’t go to Lucca?
To us, you’re going to be far happier choosing the right house for you and giving the specific geographic location far less emphasis.
Now, what about Florence? Well, what about it anyway? If your object is to see hilltowns and Florence, our advice is to visit Florence as a separate thing, either before or after your stay in the countryside. That way, you don’t have Florence to distract you as a goal. Doing it that way allows you then to go to a part of the countryside that’s just as interesting – and indeed quite often significantly more interesting – than that immediately surrounding Florence because you’ve taken care of Florence another way.
Again, to repeat what we’ve elaborated on in our essay Chianti: Is It Really for You?, to be centered around Orvieto, Spoleto, Spello, Todi, Viterbo, Assisi, is to us just as attractive – indeed in many ways far moreso – than concentrating on gift-shop-filled Radda, Castellina, Greve, Gaiole, San Gimignano.