Historically, pilgrims from Arezzo who wished to join the via Francigena, which connects Rome to Canterbury, did so via this trail from Arezzo to Siena, through Sienese territory. Over the centuries, this road has led thousands of people to Rome: down through Italy, via Tuscany and Lazio.
The areas around Siena are the final parts of Tuscany through which the Via Francigena passes before heading into Lazio. This itinerary connects with Castelnuovo Berardenga (near Siena), nestled between the hills of Chianti and the Crete Senesi.
They would start, as you will, in Arezzo, an art city with very old Etruscan roots, and successively a Roman city. In both cultures it was strategically essential.
Not far outside the city is the area called Pergine Valdarno, a hilly area in the Ambra Valley (Valdambra). One might make an interesting stop at the Santuario di Santa Maria della Neve near Castelvecchio a Migliari: this is a medieval sacred location. Next door there is a hospice for pilgrims.
One continues down to the bottom of the valley to the Presciano torrent and over to the church of San Pietro a Pieve a Presciano. Founded in early Christian times and located on a Roman road, it is documented in 1021 and was part of the abbey of Agnano. The current building is 19th century.
In the area nearby one can visit the towns of Montozzi, which is quaintly medieval and has a nice English-style park, or Montelucci, which belonged to the Gherardesca counts. There is also a natural reserve, the Bandella, a large area in which one can take in the attractive woods.
Continuing along the path and through the Ambra valley, one stops in Monteaperti in the province of Siena, the location of a bloody battle that took place on September 4, 1260, between the Ghelphs and the Ghibellines.