Castello di Bibbione, Medieval castle in San Casciano in Val di Pesa, Italy.

Castello di Bibbione is a fortified manor in the hills of San Casciano in Val di Pesa with twelve apartments that blend traditional Tuscan architecture with modern comforts. The buildings display characteristic whitewashed walls, exposed ceiling beams, and fireplaces from earlier periods.

Documented in manuscripts from 997 as Castrum Bibionis, the castle was erected by the Cadolingi of Montecascioli; its foundations date to the 9th century. From 1124 the Buondelmonti restored the ruined fortress, making it one of four castles guarding the Pesa valley. In the 15th century its defences were dismantled and it became a gentleman's residence; the Machiavelli family owned it from 1511 to 1727, and it remains with the Rangoni Machiavelli.

The estate produces wine and olive oil from surrounding vineyards and olive groves, keeping alive agricultural traditions that have defined this region for centuries. These products reflect how farming remains woven into daily life here.

The castle stands on a height above the Pesa valley, reached from the village of Montefiridolfi in San Casciano in Val di Pesa. Its agricultural land runs down to the Via Cassia and the Pesa river below. A walled courtyard, split in two by a river-pebble wall since the 15th century, lies inside.

Each apartment is furnished with period pieces and equipped with traditional fireplaces that give the rooms historical character. The pairing with modern conveniences like fully equipped kitchens creates an unexpected contrast between old and new.