Montisi is an ancient Borgo or fortified village, with a long history.
Every year on the Sunday nearest to the 5th of August there is a jousting competition between the four contradas or neighbourhoods of the village. It is the the feast day of the Madonna della Nevi,the patron saint of Montisi and the jousting competition is held to commemorate events in the history of the village.
Towards the end of the 13th Century an unpopular feudal overlord of the area, Simone di Cacciaconti, was driven away from his land by the villagers. He returned with soldiers to attack the locals and burned Montisi to the ground. He then, realising that he could not rule over Montisi with the continued opposition from the inhabitants, withdrew his army back to Siena. On his death a few years later he left his land to the religious order of the Santa Maria della Scala in Siena.
The earliest recorded evidence of the Giostra is documented in Accounts books in the Chiesa of the Madonna della Torricella dating back to the beginning of the 18th Century. It was then held in the village and continued with some breaks until the second world war. In 1972 it was re-established, as a way of bringing some life back to Montisi, which by then was in steep decline as the population moved away from the countryside to the cities.
Since then the Giostra has grown and developed: The grand medieval procession now includes 70 characters including Princes and Princesses, Dames, Knights, Councillors, Men-at-Arms, Drummers, Trumpeters and Standard-bearers. Now the Giostra has its own field set in the beautiful countryside outside Montisi. The horsemen or Fantini representing the four contradas of the village, Castello, Piazza, San Martino and Torre compete by charging at full gallop with a lance aiming at an effigy of Simone di Cacciaconti. The Effigy has a ring or campanello on his left shoulder for the top score and a target in his right arm. In his right hand he has a flagello a kind of flail with steel balls poised to strike any rider who is too slow. Each rider has four runs at the target and whover scores the most points wins the painted banner known in Montisi as the “Panno”