How to reach
From the A1 motorway towards Florence exit at the "Firenze-Signa" sign. Then take the FI-PI-LI motorway towards Livorno and leave it at the "Empoli-Ovest" exit sign. Then take the 429 provincial road towards Castelfiorentino-Certaldo-Siena. After crossing Castelfiorentino, follow the 429 provincial road up to the industrial area where you will find a narrow road on your left and a signpost with "Castello d'Oliveto" written on it. The Castle is about 4 km from there.
History
The Oliveto castle, really more a fortified villa than a castle, was built in 1424 on the top of a hill dominating the inner valley of the Pescaiola stream, tributary of the river Elsa, by the Florentine nobleman Puccio Pucci, to protect his properties and to be used as country residence or refuge in case of politic bitterness in Florence.
The castle is, beyond the real necessities of the time, endowed by moats, stone walls and towers, so it can look like a building of the previous century and not of the Renaissance. As a matter of fact the aspect of the castle, almost entirely built in red bricks, is of a classic rectangular shaped medieval fortified enclosure.
Many architectonic elements make this look stronger: the Guelph's battlements of the walled curtains (with a wall walk from which is possible to dominate the surroundings), the four imposing crenellated angle towers, (among them stand out the torre dell’orologio - clock tower), the outer ward from which, passing through a beautiful arched portal, we can access the inner ward of the Villa enriched by an open gallery and the chapel.
The inner ward contains a well that in origin was a secret way to escape from the castle: it is joined with a underground gallery that takes at the bottom of the valley. Still under construction, Oliveto was besieged from some unleashed soldier of fortune squads. It was also sacked and occupied during the war between Florence and Siena (until 1480).
During the war of the Florentine Republic against the Imperial troops, 1529-1530, Oliveto was a stronghold of the Emperor party. In 1850 the property of the castle passed from the Pucci to the Guicciardini family. Oliveto was still in the heat of a battle in July 1944. During withdrawal of the Wehrmacht toward the river Arno, the castle was defended by the 29. Panzer Grenadier Division and seat of 71° Regiment. Today the castle play the central role in an important farm holiday, wine and oil production estate.