Chìo Valley
Between High Tiber Valley, in Umbria, and Chiana Valley in Tuscany, there is a little one named Chìo Valley, characterized by a lot of Pievi (about one thousand old churches) and castles, many ruined but others incredible.
You can walk all around the valley in a day long hike, but you can also enjoy the "gate" of the valley between Castigion Fiorentino - the main town - and Montecchio Castle, both supervising the entry of the valley.
This is Castiglione Fiorentino: it's how you can imagine a medieval town...
And this is Montecchio Castle...