Montopoli in val d’Arno’s tower and arch are related to Castruccio Castracani, who is said to having been hurt during Montopoli’s siege. The arch was a part of the castle that had been destroyed as it had lost its task of military outpost. The arch was a part of the defensive system that went from the north-east tower to the castle Rocca.
Opposite the Town Hall, the imposing San Matteo’s Tower, built in 1431 by Neri Capponi, who had been sent by Florence republic in order to fortify the west part of the castle during the war between Florence and Siena. The Rocca had been destroyed in 1944, while the ancient embattled tower of the ancient castle stands still today and it became a symbol of the town.