Monteriggioni is a medieval walled town, located on a natural hillock, built by the Sienese in 1214–19 as a front line defensive fortification in their wars against Florence, by assuming command of the Via Cassia running through the Val d'Elsa and Val Staggia to the west. It withstood many attacks from both the Florentines and the forces of the Bishop of Volterra.
The roughly circular walls, totalling a length of about 570 metres (1,870 ft) and following the natural contours of the hill, were built between 1213 and 1219. There are 14 towers on square bases 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.
(Wikipedia)