Abbey of Monte Oliveto Maggiore

Nestled amidst the dramatic beauty of wild and untamed countryside, Monte Oliveto Maggiore Abbey, in the province of Siena, commands attention through the spiritual mystique of its history and the sheer grandeur of its structure. The roots of this Benedictine monastery run deep into the medieval period, when the blessed Bernardo – born Giovanni, of the noble Sienese Tolomei family – renounced worldly luxuries and wealth to embrace a life of poverty and solitude spent in the humble caves of Accona.

In this inhospitable place, which soon became a favoured destination for hermits and pilgrims, the congregation of Olivetan monks was founded in 1319. From that moment on, they would become distinguished by their white habit, a symbol of purity.

Even today, the Olivetan house retains its original character: access is gained via a narrow strip of land set between steep cliffs and ditches. The external part of the monastery is dominated by a grand tower, built in the late 14th century. Beyond this structure, a path lined with cypress trees leads onwards, at its centre stands a 16th-century fishpond. In former times, the monks used this basin to source food during periods when the monastic “rule” forbade the consumption of meat.

At the end of the path stands the austere and majestic Gothic-Romanesque profile of the abbey, construction of which began in 1401 and which today still hosts weddings and religious ceremonies. Inside, refurbished in Baroque style, the wooden lectern by Raffaele da Brescia and the inlaid wooden choir by Fra Giovanni da Verona – which spans the entire nave – merit particular attention.

Visitors’ focus, however, is primarily drawn to the great cloister, a jewel adorned with one of the Renaissance’s most important artistic cycles: the Stories of Saint Benedict. These comprise 36 grand scenes, begun in 1497 by Luca Signorelli and completed between 1505 and 1508 by Giovanni Antonio Bazzi, known as il Sodoma.

The monastery also houses an exceptionally rich library, holding approximately 40,000 volumes, booklets and incunabula (the monks continue restoration work on ancient parchments and manuscripts to this day), and an ancient pharmacy, where the friars still produce honey and herbal liqueurs. Monte Oliveto Maggiore Abbey is located near Chiusure, just a few kilometres from the better-known Asciano.

Two scenic routes lead to Monte Oliveto Abbey. From Siena, you can follow the Cassia southbound to Buonconvento, from where the road climbs to the monastery; alternatively, the second route passes through Asciano, via the ancient Via Lauretana and Chiusure, before reaching Monte Oliveto.