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The name of Monticchiello first appears in an official document in 973; Marquis Lamberto Aldobrandeschi gave it to the Arniatina Abbey in guarantee of a large loan. In following years Monticchiello became the property of the Roman church, in particular of the Teutonic Order of Knights, a company used to armed combat thus being well suited to the occupation of a border territory; they were in power until 1230. Later the Val d'Orcia was to be involved in various disputes leading to a war between the Siennese and the Florentines. The cause of the war was the claim to ownership of the "Cassero" (fortified castle keep) of Montepulciano made by both Siena and Florence. Monticchiello itself sided with Siena, which in turn took an active part in castle life and local government.

In 1249 Siena nominated the deputy who would govern Monticchiello for the chief magistrate who's seat was at San Quirico. Actually it was Siena, which controlled Monticchiello organising commanders and other military matters; in substance the role of the fortified town was that of guardian of a disputed border, a siennese base to oppose Florentines.
Montepulciano and a stronghold on the Eastern border in the direction of Maremma and Mount Amiata. Life there was certainly not peaceful: attacks, sackings and sieges followed one after another, from the beginning of 1200 to the end of 1300. The most famous defeat was brought about by the traitorous commander of the garrison in 1396 who accepted 2000 golden Florins from Florence for his act of betrayal. The city of the Giglio remained in control until 1400 when Siena once again took command.

From then on followed a long period of peace and economic development, broken in mid 1500 by the war waged by the Spanish and Germans against the French. The opposing factions looked for allies amongst the various Italian local governments ; Siena took the side of the Spanish so Monticchiello together with other fortresses of the Val d'Orcia were engaged in combat.
In the conflict which took place in March 1553 the battalions of Monticchiello fought heroically forcing the imperial troops to retreat. On the 3rd April 1559 the war ended with the treaty of Chateau Cambresis. The french troops abbandoned Tuscany and all the fortresses of the Val d'Orcia were handed over to the Medicis. On the 17th century fell into disrepair ans was abbandoned, the battalions were disbanded and part of the walls demolished.
Teatro Povero
For more than twenty years the compqny of the Teatro Povero of Monticchiello; a village perched on one of the hills surrounding Pienza, stages a particularly interesing experience of life and culture ...