An itinerary to discover the middle ages in the Valdarno area winds following the course of the Arno river, from Ponte Buriano and its ancient Romanesque bridge, along the Via dei Setteponti route, travelling along the scenic journey that thrilled Leonardo da Vinci. This itinerary leads the visitor to Castelfranco di Sopra, one of the Florentine Terrenuove (new lands), which still preserves the typical mediaeval architecture in its Florentine Gate. Among the uncontaminated landscapes not far from Castelfranco, one can visit the ancient Vallombrosan Abbey of Soffena, an Etruscan place-name, which still nowadays offers an interesting series of frescoes by the Masaccio’s brother, Giovanni di Ser Giovanni, also called “the Scheggia”.