Monticchiello di Pienza

Monticchiello rests on a hill near Pienza, in the provincial countryside of Siena. It has Roman origins, but its history is more knit into the Middle Ages. It was engaged in regular warring with Montepulciano throughout the 13th century, until Siena intervened to make peace, after which the town increased its reputation in trades and handicrafts and experienced a time of flourishing. When the Republic of Siena fell in 1559, Monticchiello was placed under the Medici powers and gradually lost its importance. It was ceded to the city of Pienza in 1778 by the Grand Duke Pietro Leopoldo.

Today's town is a charming place to wander. You enter through the Porta Sant'Agata, a Gothic gate with pointed arch flanked by two towers. There are lovely piazzas and stone streets to explore. The Torre del Cassero is an imposing structure that rises above the rooftops. There are visible remains of other towers that once stood high but have been lopped off. Monticchiello is tidy and inviting, with its cobbled streets and flower floxes. The Piazza del Teatro hosts a town tradition - the "teatro povero" (peasant theater) where the residents write and produce an annual show based on their lives in the village.