From piazza della Libertà, take via Mainardi, which runs along Contrada Mainardi, one of the first districts of the town centre and ancient Jewish quarter. There you will see a plaque commemorating Ovadyah Yare, a sharp fifteenth century Jewish man of letters and annotator of legal and religious books, known all over the Jewish world as ‘Il Gran Bertinoro’ (the Great Bertinoro).
Walking down via dei Santi, whose medieval atmosphere has remained intact over the centuries, you pass under Porta dei Tre Santi, also called porta San Romano.
You will then pass by the Abbey of S. Maria d’Urano, which was rebuilt in the 1960s on the remains of an ancient sixteenth-century Camaldolese abbey. Today the abbey houses a Clarisse convent.
From piazza Garibaldi, dominated by the monument to the homonymous hero of the Italian Risorgimento, walk down to the Chiesa del Suffragio, in which you can see the painting “The adoration of St. Benedict with three Saints” by the famous painter F. Cignani, in which the ancient town of Bertinoro is portrayed.
Walk up via dei Novelli and pass under Porta San Francesco (or porta Malatesta), and after a few steps take the cobbled via delle Mura and go straight on to the torrione San Giuseppe.