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Located on an ancient country route along the ridge, likely variant of the Via Francigena, almost certainly of Etruscan origins, the hamlet named Monti certainly dates back to at least the Xth century: in the year 929 Ugo, King of Italy, gave the site, then called Monte della Torre, to Adelardo III, bishop of Volterra.
It later belonged to the late tenth century to the Marquis Ugo of Tuscany, who assigned it to the shareholders of the Badia Fiorentina and S. Michele Marturi in Poggibonsi. At the beginning of '200 the town of San Gimignano purchased from Sigerio Lupin, gentleman of the place, the jurisdictional rights of Monti, who at that time was no longer a castle but a simple villa. Since 1200 is remembered the Church of San Bartolomeo in which are still visible rare and unique frescoes dating back to the medieval period; During the middle age it belonged to the “Cattani” a very important San Gimignano family and then probably it was a templar site. In July 1227 here San Gimignano and Colle val d’Elsa towns signed a no fight treaty.
The high prelate Paolo Cortesi (Rome 1465 - San Gimignano 1510), humanist of great value, prothonotary apostolic secretary and Brévière of Pope Julius II, made it a humanistic studies center as well as his residence, which he called "Castrum Cortesianum", which took give a look that recalls also the ancient fortified structures. In this place set up a library for public use and a cenacle where greeted his students and many personalities of the time, including Paolo and Lorenzo de’ Medici, the Dukes of Ferrara and Urbino, Pico della Mirandola, Angelo Poliziano, Marsilio Ficino, the cardinal Alessandro Farnese ( Pope Paul III) and Giuliano della Rovere ( Pope Julius II), and numerous other important members of the political and cultural elite of the time, giving the Castro Cortesiano connotations markedly cultural and public policy and making it one of the most important Italian site of european wide appeal. Here also he wrote and had printed by the famous copperplate engraver Simone Nardi, called the Red, his valuable work "De Cardinalatu" (of which there are now only 38 copies in the world, one of which is owned by the library of San Gimignano), dedicated to Julius II, which aims to set limits and rules for the Cardinal-Senator, a typical figure of the Papal States to pluck it out between the '400 and '500. The text is one of the cornerstones of humanistic literature. Thanks to the great cultural connotation that Paolo Cortesi gave the place, still Castrum Cortesianum is mentioned in the textbooks of Italian literature.