The village of Montecarlo is set on the side of the mountains that separate Valdinievole from Lucca Valley. It was built in 1333 to accommodate the inhabitants of the Community of Vivinaia, which was destroyed by the Florentines in 1331, within in the Fortress of Cerruglio.
The village was called Montecarlo in honour of Prince Charles (Carlo), son of King John of Bohemia, who liberated Lucca after it had been occupied by the armies of the Republic of Pisa.
Being in charge of the Fortress, which later proved to be a strategic garrison in the XIV century during the wars among Pisa, Lucca and Florence, the Prince came to Montecarlo several times before ascending to the throne as emperor Charles IV.
During its early history, the land of Montecarlo was under the dominion of Lucca and remained so throughout the course of the fourteenth century, with the only exception of the years 1342-1369, when it was directly controlled by the city of Pisa. In 1437, during the war between Lucca and Florence, it finally fell into the hands of the Florentines, where it remained up until the Unification of Italy. The Fortress, the historic symbol of Montecarlo, is situated on the highest point of the Cerruglio hilltop. Its oldest portion has the appearance of an isosceles triangle, with its corners connecting to the Tower of the Keep, the Tower of the Apparition and the Tower of St. Barbara.
It was later expanded upon by Paolo Guinigi, Lord of Lucca, and was completed in 1555 by order of Grand Duke Cosimo I de’ Medici. The same Grand Duke personally visited Montecarlo and ordered extensive fortification work to be carried out, including the construction of the imposing ramparts in Piazza d’Armi. When the general political conditions changed, the Grand Dukes abandoned the various expensive projects and the military constructions. Finally, in 1775 Pietro Leopoldo began disarming the Fortress which, having become the property of the City, was subsequently sold privately. Montecarlo thus took on the characteristics of a small village in which to pass delightful summer and autumn holidays and from which one could admire the splendour and vastness of the surrounding landscape.

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