Monteriggioni from a Vineyard

Monteriggioni is a small walled village, built in 1214-19 as a fortress that sits nicely upon a hill along the old Roman road, Via Cassia, the primary route from Florence to Sienna. In the day it was first built there was a lot of tension and armed animosity between Florence and Sienna.

This fortress was a protective measure undertaken by Sienna. It survived quite a number of conflicts and sieges but was ultimately handed over to the Medicis by its garrison commander Giovannino Zeti in 1554, an act of “great betrayal” to the Siennese at the time. Yet perhaps this was a saving grace to the fortress before the Florentines became more ambitious with ever increasing destructive capabilities.

The Fortress Wall and a Tower

This fortress is a tangible artifact of the many skirmishes and shifting alliances between the various city states of Italy when Pisa, Sienna, Milan, and Venice each struggled for dominance.

It was common for professional soldiers to be contracted by the warring parties to serve as tactical leaders, eg. generals, of the local militia. Giovannino Zeti was one such a military commander who changed sides several times.

Today the walled town is a pleasing and reasonably authentic example of medieval construction. The adaptations for tourists are tasteful and do not detract from the fun of stopping by for a pleasant walk around.

It is also a nice place to recharge by grabbing a cafe and panino in the restaurant. Unless it is the peak season and a tourist bus has just arrived, this is often a nice quiet stop on a Tuscan road trip.

Inside the Monteriggionini Walls

The view of the town from a nearby orchard on the other side of the main road is perhaps the best part of including Monteriggioni on a Tuscan road trip. The towers are quite interesting and its intact survival through so many conflicts, including World War II, for 800 years is most impressive.