The road from Siena to Florence has been in use for centuries, passing through charming villages, fields bursting with flowers, and gently rolling countryside. About 20 minutes north of Siena, along one bend of the road, an impressive skyline suddenly springs up: it’s the castle wall and fortified towers of Monteriggioni, a garrison town founded in the early 1200s. 

Monteriggioni was established as a defensive outpost by the army of Siena to keep watch on its long-time enemy, the Florentines. In its early days, it was almost exclusively inhabited by soldiers, officers and magistrates, along with their families. Completely surrounded by a thick stone wall, the castle-town was fortified by 14 square-based towers set equidistant from its two gates, Porta Giovanni and Porta Romea.