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Montecarlo was in the fourteenth century, an important strategic stronghold in the wars that were fought between Lucca, Pisa and Florence. The town was founded by Charles IV of Bohemia, grandson of Henry VII, in the XIV century around the fortress of Cerruglio and in his honor was named Montecarlo.
The fortress stands on the highest hill of Montecarlo and its oldest part time, dates back to the early fourteenth century, parts of the fortress are the Tower of the Apparition, the Mastio Tower and St. Barbara.
In the fifteenth century it was enlarged by Paolo Guinigi Lord of Lucca, then after becoming the possession of Florence (1437), was completed in 1555 by order of Grand Duke Cosimo I de ‘Medici. It was restored during this period the construction of the imposing bastion of the Yard. In 1775 Pietro Leopoldo put in disarming the fortress.
The Old Town, well preserved is still surrounded by beautiful walls. Of the fourteenth century doors that opened along the walls, remain only the Porta Fiorentina to Florence, the Porticciola towards Lucca, while the Porta Nuova south was reopened at the end of the sixteenth century. The fourteenth-century fortress dominates the village with well-preserved walls and a sixteenth century bastion.