The prestigious Florentine Pucci family had the castle of Oliveto built during the 15th century. The structure was intended to be a country residence and a fortification for protecting the estates the family owned in the area. Its name derives from the surrounding olive groves (the word “oliveto” means “olive grove”).

In the dismal period of Florentine history, characterized by the bloody struggle between the supporter of the Medici family and those of the Florentine Republic, the castle was the theatre of numerous battles. All the Pucci males were killed during one of these battles and the family seemed to be doomed to disappearance. Actually, a black woman servant saved the first-born. In sign of acknowledgment, the servant is represented in the family`s coat of arms.

The castle, whom the Guicciardini family acquired in 1850, when Paolina Pucci married count Luigi Guicciardini, has welcomed many illustrious personalities, such as Lorenzo the Magnificent, the two Medici Popes Leo X and Clement VII, Pope Paul III, the Grand Duke of Tuscany Ferdinand III and king Vittorio Emanuele II.

In 1944, the German army first and then the American army headquartered in the castle. During their stay, the German soldiers discovered some pictures belonging to the Uffizi Gallery in the cellars of the castle and they took them to Florence.

At present, the castle houses some pieces of furniture dating back to the 15th century and some trophies, weapons and portraits dating back to the 16th-18th centuries.