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Surrounded by woods of centuries-old oak and chestnut trees, Monticiano and its municipal territory teil a lang story of villages located on the roads which connected Siena to the Metalliferous Hills and the sea. During the Middle Ages it was under the possession of the Bishops of Volterra, and then passed under the dominion of the Municipality of Siena in the 13th century.
In the 17th century the Medici conceded it as a fief to the Counts of Elci. In the chief town, located on high ground a few kilometres from the right bank of the Merse River, you can admire the Church of Sant'Agostino with the chapter- house of the ex-convent decorated with frescoes by Bartolo di Fredi, Guidoriccio Cozzarelli and Giovanni di Paolo.
The Gothic church is an example of one of the most ancient hermitages of the Augustinian order. It was part of the same Augustinian congregation which included the convents of Lecceto, San Leonardo al Lago and Santa Lucia. Also remarkable are its Palazzo Callaini and Antico Spedale, transformed into a church, where there is a curious decoration under the side-door: a snake with a lily in its mouth. The hamlet of San Lorenzo a Merse preserves its ancient Romanesque castle and church.
At the border with the territory of Grosseto is Petriolo, a spa which was already famous in the Roman age, and a rare example of a fortified medieval spa of which a great part of the quadrangular city wall in stone still remains.
Spacious and uncontaminated landscapes are found when you reach the city centre of Castello di Tocchi, interesting for the typical structure of the village with its arched entry gate still weil preserved, the ruins of the fortifications of Castellaccio, Monte Quoio and Renna.
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