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

Castello di Gabbiano is a medieval castle located on elevated grounds between Florence and Siena in Tuscany. The property spans about 100 hectares of vineyards, olive groves, and woods, with accommodations in eleven rooms, a restaurant for dining and wine tastings, a swimming pool, and offers cooking classes and ceramic workshops.

From the early 15th century the castle belonged to a branch of the Bardi family, then passed to Tommaso Soderini, father of Pier Soderini, Gonfaloniere of the Florentine Republic. After the Medici returned to power the Soderini were banished and the castle stood abandoned until 1623, when it was returned to its former owners in poor condition, as a plaque above the entrance door records. The four cylindrical corner towers were added after the mid-15th century, as at Meleto Castle near Gaiole in Chianti.

The castle functions as a working wine estate where Chianti Classico and other Tuscan wines are produced from grapes grown on the grounds. This wine production shapes the daily rhythm and identity of the property.

The property sits on elevated terrain offering good views of the surrounding landscape, though reaching it involves some climbing from lower elevations. Visitors should plan time to explore the vineyards and buildings at a leisurely pace.

Each room in the castle features its own design with distinct color schemes and furnishings, creating an individual experience for every guest. This variety is achieved while respecting the medieval structure and providing modern comfort throughout.