The Via Lauretana is an ancient Etrusco-Roman road that connects Cortona to Montepulciano and Siena. Used and expanded like so many other Roman roads, it was conceived as a link between Cortona and the Etruscan cities on the sea. It then became a pilgrimage route, which for centuries connected Siena, and therefore the Via Francigena, with Cortona, spanning six Tuscan municipalities as it winds towards the Santa Casa of Loreto.
A heavily-trafficked road in the fifteenth, sixteen and seventeenth centuries, it deviated from the Via Francigena at Siena and led to Camucia, at the foot of Cortona, via Asciano, Sinalunga, Torrita di Siena and Montepulciano, crossing the walled bridge over the River Clanis to arrive at the castle of Valiano, and finally Cortono itself. From Cortona, the ancient Via Lauretana hugged the eastern shore of Lake Trasimeno as it went through Passignano, clipped Perugia and continued in the direction of Foligno, in Umbria. From here it unfolded towards the Appenines of Umbria and Le Marche, conquering the heights of the Colfiorito Pass and finally reaching Loreto, in Le Marche.