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Our village is an ancient one, with a long history of which we will try to give a brief account here.
It is very likely that before the Romans came to these hills, known as the Monti of Trequanda, their earliest inhabitants were the Etruscans, who settled between the Tyrrhenian Sea and the valleys of the Arno and the Tiber around the 8th century B.C. It has been daimed that Montisi gets its name from a temple dedicated to the goddess Isis, venerated by the Etruscans, that used to stand a couple of kilometres from the village.
The earliest reliable documents date back to the 12th century, when Montisi was a castle belonging to the Counts of the Scialenga, originally from Asciano. To be precise they were members of the branch of the Cacciaconti who acknowledged the sovereignty of the Commune of Siena around 1175. About thirty years later the heads of families from Montisi about a hundred people in ali, took part in the general swearing of allegiance to Siena required of ali the communities under the rule of the Scialenghi.
Since one of the requirements of this pact of vassalage was that the Cacciaconti should reside in the city for at least three months out of every year, they began to play a part in the political and commerciai life of Siena, thereby relaxing their control over Montisi, to the point where they started to lease the lands to their cultivators . Thus began the process of evolu tion that was to lead to the formation of the free Commune of Montisi or Monte Isi as it is called in contemporary documents.
By 1283 Montisi was already organized into a Commune with its own "massari" or bailiffs.
In 1291 three Cacciaconti brothers, Simone, Fazio and Cacciaconte, drew up a de ed stipulating the division of claims to and revenues from the village and castle of Montisi.
It is probable that the Montisani did not willingly accept direct rule by Simone Cacciaconti who was obliged to attack the castle at the head of a group of men-at-arms a year later, taking it only after fierce combat.
Three of the defenders were killed and others wounded. When Simone withdrew, having realized that he could not impose his rule without leaving a strong garrison to occupy Montisi he burned down the village and despoiled its inhabitants of all their possessions and castle.
The Commune of Siena, to which the Montisani appealed for justice, banished the Cacciaconti but this did very little to relieve the misery and suffering of the village's inhabitants .
The memory of this episode has been kept alive to this day in the Giostra di Simone, staged in Montisi every year on the afternoon of the Sunday closest to August 5, the feast-day of Montisi's patron, Our Lady of the Snows.
The knights who represent the four Contrade or quarters - Castello, Torre, Piazza and San Martino - compete in the tourney by attempting to strike the "buratto" with their lances at the end of a ride at full gallop. The "buratto" is a wooden effigy of the wicked Simone, bearing a target in its left hand and a ring known as the "campanella" over the same shoulder, while the figure's right hand holds the "flagello", a sort of whip with balls attached to the lash, designed to strike the horseman's back if he is not fast enough in his attack. Each knight carries out four "carriere" or charges, in which he can choose to strike the target or to impale and carry off the "campanella" widh his lance. The Contrada whid accumulates the largest number of points is awarded a painted banner, called "Il Panno" in Montisi. The Tourney is preceded by a parade in costume, in which representatives of the four Contrade, the "massari" of the Commune, armigers, drummers and players of "chiarine" long silver trumpets that produce a martial sound, all take part.
The fate of Montisi to go backe to the story, became more and more closely bound up with that of Siena, getting involved in the war with Florence and the internal conflicts between Guelphs and Ghibellines.
Towards the end of the 13th century, the powerful Hospital of Santa Maria della Scala in Siena inherited the castle and the estates around Montisi from Simone Cacciaconti and, at the end of the 14th century, built the Grancia, an imposing fortified farm of brick, with moats, a drawbridge, a fine cloister, cellars, water cisterns and oil-presses, overlooked by a slender tower similar to that of the Town HaO in Siena Unfortunately, some six centuries later the tower was blown up by German troops as they retreated from the advance of the Allied forces. From 1371 onwards the castle of Montisi was the sec of a Vicar of the Commune of Siena, with authority over the nearby castle of Montelifrè as well.
At that time the castle of Montisi occupied the entire summit of the hill overlooking the village, with a square tower or keep at the top which was destroyed towards the end of the 14th century. A wall, part of which is still standing, surrounded the castle and an elliptical road, the present-day Via del Castello, served as a beat.
In 1494 the new Statute of the Commune of Montisi was approved, but the political and economic decline of Siena and the surrounding countryside had already begun, culminating in the 16th century in the fall of the Republic of Siena. Bands of French and Spanish mercenaries in the pay of the Medicean rulers wandered the territory in search of plunder. Thirty years later Siena's glorious em of independence was at an end. Cosimo dc' Medici succeeded in defeating the Sienese Republic for once and all. annexing ali its territories and domains, including Montisi, to the Grand Duchy of Tuscany. As a last vestige of independence, Montisi was allowed free elections for the Prioral Council and the Camerlengo, but the population was placed under the control of the Podesta of Trequanda, while the administration of justice was entrusted to the Magistrate of Pienza.
Dark centuries followed, centuries of great poverty in the Sienese countryside, although the situation was slightly better in Montisi because of the cultivation of saffron, which provided a modest additional income alongside that derived from more traditional crops.
At the end of the 17th century, the population of Montisi was made up largely of peasants, almost ali working for payment, together with a few artisans, comprising carpenters, cobblers, blacksmiths and an armourer. In the 18th century the Hospital of Santa Maria della Scala, burdened with debt, made over the Grange of Montisi to the Mannucci-Benincasa family, whose descendants live there to this day.
The Community of Montisi ceased to exist in 1777, when Grand Duke Leopoldo of Tuscany assigned Montisi along with Petroio and Castelmuzio, to the Commune of Trequanda as part of a series of reforms aimed at bringing into line the various statutes inforce in the territory of the Grand Duchy.
Relations between the Commune and these three wards deteriorated towards the middle of the 19th century and Montisi applied and was granted permission to become part of the Commune of San Giovanni d'Asso.
There was a special reason for this choice: the Commune of Trequanda was in fact unable to meet the water requirements of Montisi and a certain Signor Croci of San Giovanni d'Asso had promised to provide a spring for the people of Montisi on the understanding that the village be transferred to his Commune.
On january 1,1878, in accordance with a law signed by Victor Emmanuel II, the King of Italy, Montisi became a ward of San Giovanni d'Asso.
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