Originally an Etruscan settlement, Certaldo owes its name to the former appearance of the hill on which it stands. Its name is believed to come from the Latin cerrus altus or from the Germanic cerrus aldo – in either case, two short descriptions of the oak-covered highland. Two significant dates in the history of Certaldo were 1164, when the Emperor Frederick Barbarossa conceded the dominion to the Alberti counts of Prato, who took up residence in Palazzo Pretorio; and 1184, when the town fell under the rule of Florence. The family of Giovanni Boccaccio (1313–1375) was from Certaldo, and the writer lived in the town at various points in his life in the house that still hosts the Museum and National Association named after him.
The old town centre, also known as Castello, is the part within the walls into which the old Porta Alberti, Porta al Sole and Porta al Rivellino gates lead. You can access the old centre by climbing up the steep streets costa Alberti and costa Vecchia, from the more modern via del Castello or by using the funicular railway that leaves from piazza Boccaccio. A unique features of the town is that, unlike other villages dating to the Middle Ages, Certaldo has no main piazza, the place where the religious, political, civil and commercial powers usually made their mark. Certaldo developed instead along a lengthened hill, where it was believed there was no space for a public area, whose function was adopted by the present-day via Boccaccio, lined with the church, Palazzo Pretorio and the market loggias, now walled up but whose blind arches can still be seen on the walls of Palazzo Stiozzi Ridolfi. The piazzas we see today were none other than allotments, used to feed the population in case of siege.
The most important monument in Certaldo was Palazzo Pretorio, the former home of the Alberti counts, which was erected in the late 12th century on the remains of this family’s older dwellings. The prisons, reception rooms, archive, chapel and the private lodgings of the vicars can still be visited today. On the facade and inside the palazzo numerous shields are on display, each of which represents the effigies of the family of every vicar who ruled the town. In the palazzo you can admire frescoes and sinopies dating to the 15th and 16th centuries. Next door to the palazzo stands the church of San Tommaso e Prospero, dating to the 13th century.The Museum of Sacred Art is worth a visit, contained in what was originally a 15th-century Agostinian monastery. The exhibition halls are dedicated to painting, sculpture and holy vestments. In the picture gallery, once the monastery’s refectory, you find paintings from the 12th to the 16th century, with art by Cenni di Francesco di Ser Cenni, Ugolino di Nerio and Meliore. The wooden crucifix from the church of San Pietro a Petrognano is striking, dating to the first half of the 13th century, artist unknown. It is unique in the world of medieval Italian sculpture: the image of Christ, triumphant over Death, has gained much recognition in art criticism thanks to the sculpture’s expressive force.