Monteriggioni is a medieval walled town, located on a natural hillock, built by the Sienese in 1214-19 as a front line in their wars against Florence, by assuming command of the Via Cassia running through the Val d'Elsa and Val Staggia to the west. During the conflicts between Siena and Florence in the Middle Ages, the city was strategically placed as a defensive fortification. It also withstood many attacks from both the Florentines and the forces of the Bishop of Volterra. In 1554 the Sienese were able to place control of the town's garrison to Giovannino Zeti, who had been exiled from Florence. In 1554, in an act of reconciliation with the Medicis, Zeti simply handed the keys of the town over to the Medicean forces— considered a "great betrayal" by the town's people.
Main sights
The roughly circular walls, totalling a length of about 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. The main piazza, the Piazza Roma, is dominated by a Romanesque church with a simple, plain façade. Other houses, some in the Renaissance style face into the piazza. Off the main piazza smaller streets give way to public gardens fronted by the other houses and small businesses of the town. In more hostile times, these gardens provided vital sustenance when enemies gathered without. Other sights in the town's countryside include:
Badia of Santi Salvatore e Cirino, at Abbadia Isola, a Romanesque abbey from the mid-12th century.
Romanesque church of San Lorenzo a Colle Ciupi
Romanesque Pieve of Santa Maria a Castello, known since as early as 971
The Tuscan poet Dante Alighieri used the turrets of Monteriggioni to evoke the sight of the ring of giants encircling the Infernal abyss. Monteriggioni also plays a significant role in the games Assassin's Creed II and , both of which are loosely based around certain key historical events in Renaissance Italy. It is home to protagonist Ezio Auditore, and his uncle Mario, who lives in the fictional Villa Auditore.
Monteriggioni is headed by a mayor assisted by a legislative body, the consiglio comunale, and an executive body, the giunta comunale. Since 1995 the mayor and members of the consiglio comunale are directly elected together by resident citizens, while from 1945 to 1995 the mayor was chosen by the legislative body. The giunta comunale is chaired by the mayor, who appoints others members, called assessor . The offices of the comune are housed in a building usually called the municipio or palazzo comunale. Since 1995 the mayor of Monteriggioni is directly elected by citizens, originally every four, then every five years. The current mayor is Andrea Frosini, elected on 26 May 2019 with the 43.3% of the votes.