Castello di Colle Massari, Medieval castle in Cinigiano, Italy.
Castello di Colle Massari is a stone fortress sitting on a hilltop in Tuscany, featuring traditional medieval architecture with interior courtyards and thick defensive walls. The complex includes multiple residential buildings, guest accommodations, cellars, and expansive grounds with vineyards and olive groves that form a working agricultural estate.
The castle was built in the 1200s as a fortified settlement under the Republic of Siena's control in this region. Over the following centuries it changed hands as political power shifted across Tuscany, while its stone walls remained a constant landmark on the landscape.
The estate functions as a working organic wine and olive oil producer, where visitors can observe traditional Tuscan farming practices in action within the castle grounds. The integration of medieval stonework with current agricultural work shapes how the place is experienced today.
The property offers overnight stays in rooms and villas, plus cooking classes and wine tastings that let guests experience how the estate operates. Spring and autumn are the most active seasons when farming work is visible and the weather is comfortable for exploring the grounds.
The entire property has been certified organic since it began operating, making it one of the earliest estates to merge medieval stonework with contemporary sustainable farming methods. This combination is rare in rural Tuscany and creates an unusual rhythm where ancient structures coexist with modern ecological practices.
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