Palazzo Massaini can be found just over 4 kilometres from Pienza, spreading over the rolling hills of the Val d’Orcia Artistic, Natural and Cultural Park, a UNESCO world heritage site since 2004 – a prime location for its beauty, history and culture. It boasts an extraordinary view that seems frozen in time. Here the shapes and colours of nature change with the seasons, suggestive of the harmony shown in the Sienese School of painting. 


The origins of Palazzo Massaini date to around 1200 when it was built by Bibbiano Cacciaconti, a member of the aristocratic Asciano family.

In the 16th century, the building was converted into a “villa” and a wing was added, as well as an elegant little loggia in the courtyard and understated cornices to the gates.

Amongst the many owners it would have over time, we have one Pope – Enea Silvio Piccolomini (1405-1464), who became Pope Pius II in 1458. The coats of arms of the Piccolomini family are evident inside the Castle, especially the so-called “light blue cross with the moons of God”.

Today the architectural complex features an Italian garden which spreads to the east of the villa.


Olive groves and vineyards for as far as the eye can see – but that’s not all! Complete immersion in nature, a breathtaking view, and tasting sessions of the wine and olive oil that you can buy right there or on the Palazzo Massaini website. The vine groves are cultivated on sloping, deep, silty-clayey soil at altitudes between 400 and 500 metres, extending for around 12 hectares. A little under 11 hectares are Sangiovese vines (red grapes), while the rest is divided equally between Merlot (red grapes) and Trebbiano/Malvasia (white grapes).

The olive groves are spread over uneven, sloping terrain at altitudes between 400 and 500 metres, taking up around 15 hectares. They are divided into 4 areas: the olive groves “below the Palazzo” (Pienza side), the Cavarciano olive groves, the La Pieve olive groves, and the La Renaia Farmhouse olive groves.