The wide Valdichiana (Chiana Valley) has been an agricultural area since at least the 3rd century B.C., when Hannibal fed and provisioned his entire army here, elephants and all, before marching off to defeat the Roman legions at Lake Trasimeno. From the fall of the Roman Empire until the era of the Tuscan grand dukes, the untended valley reverted to boggy marshland, leaving only the craggy cities on either side. On the eastern fringe they included Castiglion Fiorentino and Cortona. The western side of the valley borders Siena's province and is dominated by Monte San Savino, Lucigiano, and Sinalunga.
Exploring the Region by Train -- Train service from Arezzo to Sinalunga -- stopping at Monte San Savino and, albeit a bit far away, Lucignano -- is operated by the private firm LFI, not FS (the state railway). For LFI info, call tel. 0575-22-663 in Arezzo.