Montisi is located about half way between Rome and Florence, in southern Tuscany. Siena lies to the north while the wine towns of Montepulciano and Montalcino are about 10 miles away to the south and to the west. The nearest railway station is Sinalunga, and the autostrada A1 passes to the east with an exit at Valdichiana, on the way to Perugia. The village itself is sited on the ridge of hills separating the broad Val di Chiana and the Crete Senesi, a unique landscape of rolling downland.
Montisi is an ancient village. It is very likely that before the Romans came to these hills, known as the Monti of Trequanda, the earliest inhabitants were Etruscans who settled between the Tyrrhenian Sea and the valleys of the Arno and the Tiber around the 8th century B.C. It is likely 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. They were a branch of the Cacciaconti family, 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 all, took part in the general swearing of allegiance to Siena, required of all 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 commercial 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 evolution 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 deed 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 cattle. 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 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 tournament by attempting to strike the target with their lances at the end of a ride at full gallop. The target, or 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 with his lance. The Contrada which accumulates the largest number of points is awarded a painted banner, called Il Panno in Montisi. The tournament is preceded by a parade in costume, in which representatives of the four Contrade, the massari of the Commune, armigers (weapon bearers), drummers and players of chiarine, long silver trumpets that produce a martial sound, all take part.
The fate of Montisi, to go back 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 Hall 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 see 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 era of independence was at an end. Cosimo d' Medici succeeded in defeating the Sienese Republic once and for all, annexing all 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 Camarlengo, 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 all working for payment, together with a few artisans, comprising carpenters, cobblers, blacksmiths, and an armorer. 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 Leopold 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 in force 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.
After the convulsions of two world wars, Montisi tried its hand at mining (there were several lignite mines in the hills above the village, which had a population of nearly two thousand people at one stage), and at terracotta manufacture. Meanwhile, agriculture was changing. A tide of Sardinian sheep farmers arrived in Tuscany, bringing their knowledge of sheep husbandry and cheese making. This changed the face of the countryside, as large flocks of sheep were pastured on the Crete Senesi, which up until then had been rough downland, with its calanche or biancani (steeply eroded clay canyons), and its deep purple wild clover called sulla. Then in the 1970s, the first foreign tourists arrived, attracted to this area perhaps as overspill from the more frequented tourist hotspots, and the development of a world-class wine industry nearby. Olive oil became a staple of the local economy, and indeed some of Italy's most highly prized oil producers are based in Montisi and the nearby villages. The abandoned farmhouses, and the empty apartments in the centres of small villages, slowly took on a new life, as "foreigners" from other parts of Italy and the rest of the world sought the peace and tranquility of this extraordinary landscape, either as a stimulus for their own creative lives, or as a rest from their activities elsewhere. Montisi now boasts shops, places to stay, a 100 seat cinema, 70 seat historic live theater, artists' workshops, a music school, 6 places to eat and drink, and a thriving local economy. The changing face of a village that within living memory had been reduced to just over two hundred inhabitants now is the liveliest spot in the area and a magnet for locals and visitors alike.