Assisi, in Umbria, is a hill town of great note. From Montepulciano, an hour drive makes a great daytrip. The Basilicas of Saint Francis (San Francesco) and Saint Clare (Santa Chiara) are located there as are several other interesting churches. Some churches allow photos, but many do not, especially if there are masterworks on the walls. Within these churches are stunning works of art in tribute to these saints and the start of the Franciscan order.
In the valley below is the Basilica of Santa Maria degli Angeli, a must see if in the Assisi area, and within this church is housed the tiny church the Pope gave to Francis.
While crowded during the height of tourist season, there is generally ample parking in Assisi, but be prepared to walk.
There is a multitude of places to eat and enjoy the scenery.
Out from Assisi is the valley of the Tiber River (Fiume Tevere) with a mix of farming and industry associated with nearby Perugia.
Throughout Italy are castles and fortifications from the medieval and renaissance periods of Italian history. One of the more interesting fortifications is in the small Tuscan town of Sarteano. The castle withstood attack several times, including the forces of Cesare Borgia. From the castle, a vast 60 km distance may be viewed. In the day, those watching the surrounding area of the Valdichiana could see Assisi, Chiusi, Montalpulciano, Cortona, Lake Trasimeno and the distant approaches to Sarteano. The castle has few windows and rooms for the captains of the fortress and their families, and gives a good sense of what it would be like to live there.