On your way from Siena to the sea you cannot miss the castle town of Paganico, truly worth a visit.
The development of Paganico and its transition from simple village to a walled village, is linked to the domination of this area of the Maremma by Siena that began in 1193. The fortified settlement, situated at the confluence of river Ombrone and stream Lanzo, was built along the road that comes from Siena passing by San Lorenzo a Merse and Forcole and ends with Roselle and Grosseto. This gave rise to a bulwark in the heart of the new southern domains of Siena. To facilitate its development, the settlement was made tax-free so that its first name was Castelfranco Paganico (franco means without taxes). To increase its importance, in 1294 the village became a regulated market and as a “mercatale” it became the most powerful tool to destroy the old feudal economic system of the area, by then already controlled by the Ardengheschi family. To complete the elevation of its ranks, starting with 1303 Paganico was made a Vicarship. The damages caused by the mercenary and the malarial Maremma, at the time dotted by swampy marshes, caused the depopulation of Paganico and its subsequent decay by the middle of 1300. In 1494 the village was sacked by the troops of Charles VIII. It then passed under the control of the Medici. It was only with the 18th century swamps drainage that the area started to experience an economic and social revival.
The first boundary wall of 1278 was destroyed in 1328 by Castruccio Castracani. Soon after, in 1334, the second circle was erected under the direction of architect Lando di Pietro, the same as the Duomo of Siena. The walls have the shape of an irregular quadrilateral, almost a trapezoid, with square towers placed at regular intervals, massive corner towers, four doors at the ends of the two main roadways. A high forecastle or keep, that in the Medici era was transformed into a less austere and more elegant building, is located beside the North Gate also called Sienese. The North and South Doors at the ends of the main street were equipped with a small reef or frontispiece. Apart from the east side walls, now completely disappeared with the door, the walls that surround the town are more or less intact. The Porta Grossetana, or Porta Franca, and Porta Senese, are very beautiful and intact. Both have the characteristic pointed arch superimposed on a low round arch surmounted by the black and white crest of Siena. The West Gate is still mostly intact.
The village plan is geometric, like all settlements that are a result of strategic planning. Some fine medieval palaces and porches are still intact, and in the main square is the recently-restored original water well. The Romanesque San Michele church built between 1296 and 1305 is in the main square. It hosts two cycles of frescoes of the Sienese school attributed to Biagio di Goro Ghezzi.
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