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Val di Chiana is a large flat area, crossed by the river Chiana, which is located southwest of the city of Arezzo. The river Chiana, an ancient tributary of the Tiber, was diverted by the Romans so that its waters flowing to the Arno, thus reducing the risk of flooding of the Tiber in Rome. 

The Val di Chiana in ancient times was considered the breadbasket of Etruria, thanks to the fertility of the soil and the richness of its crops. The valley was also crossed by two major Roman road, the Via Cassia (vetus) and the Via Clodia, the main settlements in Etruscan and Roman times were Cortona and Chiusi.

During the Middle Ages the territory of the Val di Chiana suffered a gradual abandonment of the valley, caused by waterlogging in most of the area, then developed the hill towns of Montepulciano, Castiglion Fiorentino, Monte San Savino, Lucignano, Civitella Val di Chiana etc.. From the seventeenth-eighteenth century the area was reclaimed and agricultural activities met a new prosperous period. Today the area is divided between the provinces of Arezzo and Siena, are part of the towns of Castiglion Fiorentino, Civitella in Val di Chiana, Cortona, Foiano della Chiana, Lucignano, Marciano della Chiana, Monte San Savino in Arezzo province, and Cetona, Chianciano Terme, Chiusi, Montepulciano, San Casciano dei Bagni, Sarteano, Sinalunga, Torrita di Siena, and Trequanda in Siena province.