Palazzo Massaini

Region: Toscana

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The central structure of this historical residence consists of several buildings clustered around a stone tower, the architectural element that characterises the castle, with a protruding base and lowered arched windows, which are most probably original. The ancient origins of Palazzo Massaini date back to around the year 1200.



The ancient origins of Palazzo Massaini date back to around the year 1200 when it was built by Bibbiano Cacciaconti, a member of the noble family of Asciano. This fortress was once under the domain of the Scialenga Counts, but its feudal autonomy came to an end quite early, in 1213, unlike other castles in the area that resisted Sienese expansionism for centuries. In the 16th century, it was transformed into a ‘Villa’, when the most prominent figure to inhabit it was Girolamo Massaini, a member of the noble Massaini dynasty of Siena. Canon Mannucci, in his book on Pienza, art and history, describes Girolamo Massaini as an orator for his homeland (i.e. Siena) in Rome in 1527, at the time when his presence there was most likely to negotiate peace with Pope Clement VII. Subsequent owners included the Placidi, Piccolomini, Bologna and Dei families. It is well documented (at the time of a ‘motu proprio’ document) that Palazzo Massaini was one of the five communes of the Pienza community in 1771. There was a total of 336 inhabitants living in the entire village in the year 1833.

Without a shadow of a doubt, the most illustrious name of all the castle's many owners is that of Enea Silvio Piccolomini (1405-1464), who was born in Corsignano (later renamed Pienza, the town of Pio) and later became Pope under the name Pio II in 1458. Within the Castle, the heraldic crests of the Piccolomini family are clearly visible, in particular the so-called 'blue cross sprinkled with moons of God'. However, there is also the Habsburg coat of arms of the double-headed eagle: this was conferred by Emperor Frederick III of Austria on the Piccolomini family in recognition of work carried out as his secretary and advisor.



The Wine Shop is located on the ground floor of Palazzo Massaini, where it is possible to buy or taste our wines and extra virgin olive oil.

The private park with its elegant Italian-style garden features stunning architectural elements including statues and a central fountain, all seamlessly integrated with the selected vegetation to convey the concept of a lavish garden.

Currently, interior tours of the Palazzo are not available. The outdoor areas can be visited free of charge at any time.

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