Numerous documents, mostly from the 1600 and 1700s, reveal that the preferred stops along the pilgrim itinerary were made in the Florentine Valdarno, Palazzolo, Troghi and Figline, Levanella and Ponte a Buriano. The route led to the Val di Chiana until reaching Cortona, and then travelled to Foligno, passing through Assisi and Perugia. Past the Valico del Col Fiorito, it travelled through the Chienti Valley, until Recanati, and finally Loreto.
This route was first documented in the late-Middle Ages, when it was thought to be more popular among pilgrims than the Via Francigena to reach Rome. It was represented by the so-called Via dell’Alpe di Serra, a route which lead from the Via Emilia, along with ten or so other paths, between Bologna and Forlì, reaching Bagno di Romagna, through the Bidente Valley, and then teading ot the top of the Apennines.
Today, Via dell’Alpe di Serra has been largely abandoned in favour of the Pass of Mandrioli. In years past, the "Vecchia Aretina" travelled through the Casentinesi forests, running parallel to the Arno river, until reaching Arezzo. It then continued to Rome, travelling through the Val di Chiana and the Val Tiberina.
Arezzo, the first city that pilgrim's encountered after the Apennines, wasn't just an important resting place but also important for its position because a number of pilgrim's paths converged there from other nearby valleys. The path also joined the Via Cassia, which ran along the Arno river in the upper Valdarno Valley, in the direction of Florence.
Throughout the Middle Ages, in fact, the route continued to have an important function, despite that fact that it lost its appeal as the preferred route to Rome. Instead, it was primarily used to travel from Florence to Arezzo, travelling through the upper Valdarno. This is why numerous markets were opened along the route, leading the Florentine Republic, in the 1300s, to establish one of its 'terrenuove' there (like Castel San Giovanni), aimed at conquering one of its last feudal areas and thus gain control of the entire territory.
Between the 1400s and the 1500s, the Loreto Sanctuary became an important stop for pilgrim's from the West, allowing the Valdarno to grow in size and importance. The road that led to Arezzo became, in fact, the first route for all people from Florence who wanted to is it the Rome.