Retracing the steps of the pilgrims and travelers who voyaged to Rome from Northern Europe along the Via Cassia in the Middle Ages, we find San Casciano in Val di Pesa, still today showing important traces of its ancient walls, Tavarnelle Val di Pesa, originally formed of three villages, and Barberino Val d’Elsa, founded by the Florentines in a strategic position, its medieval urban grid still intact.
In the vicinity of Tavarnelle an interesting stop can be made at San Donato in Poggio, a town that still preserves large sections of its ancient walls, numerous 13th- and 14th-century buildings, and the Romanesque parish church of Saint Donato.
Travelling from here along the Via Chiantigiana, we come to Greve in Chianti, a town that grew up around its big central square, starting in the 12th century, as a “mercatale”, or marketplace, for the nearby castles. Overlooking Greve is the castle of Montefioralle, whose original structure of medieval village remains entirely unchanged. Going backs towards Florence, we arrive at Impruneta, a town that developed around the Pieve di Santa Maria, a parish church founded in 1060.
From Impruneta, along the Via Vecchia Aretina, one of the so-called “Vie Romee”, we can follow the course of the Arno River to find, between Bagno a Ripoli and Rignano sull’Arno, the Benedictine Abbey of S. Maria in Rosano. We then go on to Incisa in Val d’Arno, dominated by the Tower of its 14th-century castle, and lastly to Figline Valdarno, surrounded by a belt of walls that has remained almost intact.
Going towards Reggello, in the direction of Montagna Fiorentina , we will find instead the millenarian Pieve (parish church) of San Pietro in Cascia, from where we can enter the famous Forest of Vallombrosa, a natural area rich in vegetation with numerous waterways.