Cerreto Guidi has beautiful hills and plenty of land covered with vineyards and olive groves, making it a sort of "cultivated garden" that bears the imprint of the farming efforts made, over the centuries, by its inhabitants. In addition to the turkey oak groves that stand on the edge of the settlements and which once helped determine its name, joined later by that of the Conti Guidi, medieval feudal lords from Casentino, the area is characterised by long rows of vines and extensive olive groves. And the wine and oil that are produced on these lands are appreciated, both locally and by visitors and tourists.
The sense of belonging in our community is very strong, particularly during festivals and commemorations, which come to life thanks to the four town districts and the numerous associations that help organize them. These include “La Notte d’Isabella”, the “Palio del Cerro”, “Medicea”, “La Via dei Presepi” and the two religious festivals loved by visitors: l’Infiorata del Corpus Domini and the Festa di Santa Liberata, the town’s patron saint together with St Leonard.
A defining feature of Cerreto Guidi is the Villa Medicea at top of the town. Built for Cosimo I de’ Medici in the second half of the 16th century, it has recently become a UNESCO world heritage site. It was used as a hunting lodge (nearby is the "Barco reale mediceo") and as a place of territorial control, especially of the Padule di Fucecchio – an extensive wetlands, then full of fish, whose borders reached the edges of Cerreto’s territory. Part of the villa's fame is tied to the figure of Isabella "Stella di Casa" Medici, Cosimo I’s favourite daughter, a beautiful and cultivated woman who – for family gain - was forced to marry the roguish Paolo Giordano Orsini. One day while heading off on a military campaign, he entrusted her to his cousin Troilo, who was far more refined than he. Between wife and guardian, love blossomed. Later she was discovered by her husband, who decided to take revenge. To do so, he invited Isabella to the Villa and dropped a noose through a hole in the ceiling, strangling her in the bridal chamber. Since then, the woman's ghost has haunted the rooms of the mansion. She was last sighted in 1953, when she appeared to some American actors making a film. Several US newspapers reported the incident. Today we remember the story by hanging a noose from the ceiling of the bridal chamber.
Adjacent to the villa is the ancient Pieve di San Leonardo, where you’ll find a priceless baptismal font made from glazed earthenware in 1511 and attributed to Giovanni della Robbia. It’s decorated on all six sides in high reliefs depicting the life of St John the Baptist. Also in the centre of town is the Oratorio della Santissima Trinità, where there’s a work of art from the end of the '500s attributed to Passignano. It’s the “Messa di San Gregorio”.