Monteriggioni

Monteriggioni is a walled town built by the Sienese in 1214–19 as a front line in their wars against Florence. There are 14 towers set at equidistance, and two portals or gates. One gate, the Porta Fiorentina opens toward Florence to the north, and the other, the Porta Romana, faces Rome to the south. The main street within the walls connects the two gates in a roughly straight line.

During the conflicts between Siena and Florence in the Middle Ages, it also withstood many attacks. In the 15th century, the city walls were reinforced to withstand artillery. In 1526 the fortress withstood a siege by the Florentines, who attacked the fortress with artillery. In 1554 the Sienese placed control of the town's garrison to Giovannino Zeti, who had been exiled from Florence. A few months later, in an act of reconciliation with the Medicis, Zeti had the city gate opened, which allowed the troops from Florence to enter and take possession of the place. This was considered a "great betrayal" by the town's people.