Arguably one of the most interesting among the trails criss-crossing the Valdichiana, this path runs from the hamlet of Ossaia, the discovery site of a superb roman villa nestled amidst olive groves on the hillside of Sepoltaglia; there the medieval church of Santa Maria is all that is left of the ancient castle guarding this strategic point providing an all-round view over the nearby hills and valleys. Hidden amongst the olive-groves, the, now ruined, tiny church of San Donato was built on ancient Etruscan foundations.