Monte Oliveto Maggiore 
A very interesting excursion from Siena is to the large monastery of Monte Oliveto Maggiore (273m/901ft). One of the most renowned monasteries of the Olivetans (a branch of the Benedictines), it was founded in 1313 by Bernardo Tolomei.
The Abbazía di Monte Oliveto Maggiore, seat of the Abbot-General of the Olivetans, an independent branch of the Benedictine Order, lies some 30km/20mi southeast of Siena, off the road from Asciano to Buonconvento.
The Abbazía di Monte Oliveto Maggiore, seat of the Abbot-General of the Olivetans, an independent branch of the Benedictine Order, lies some 30km/20mi southeast of Siena, off the road from Asciano to Buonconvento.
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Must-see attractions nearby:
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To the north extends the lunar landscape of the Crete.
History
The abbey was founded by a teacher of law, Bernardo Tolomei, who withdrew to this remote site with two friends in 1313 to lead an ascetic life in accordance with a strict interpretation of the Rule of St Benedict, on the principle of "ora et labora" ("pray and work"). In 1319 the monks received episcopal approval and in 1344 papal authority for the establishment of their Order. The abbey soon developed into a flourishing community, was several times enlarged and became a center of spiritual and cultural life.
Abbey
The abbey precincts are entered through a fortress-like gate tower built from 1393 onwards, with notable terracotta reliefs of the school of Luca della Robbia. The conventual buildings, in brick, were erected in stages between 1387 and 1514, with some later restoration. The imposing church (early 15th century; remodeled in Baroque style) has beautiful choir-stalls.
History
The abbey was founded by a teacher of law, Bernardo Tolomei, who withdrew to this remote site with two friends in 1313 to lead an ascetic life in accordance with a strict interpretation of the Rule of St Benedict, on the principle of "ora et labora" ("pray and work"). In 1319 the monks received episcopal approval and in 1344 papal authority for the establishment of their Order. The abbey soon developed into a flourishing community, was several times enlarged and became a center of spiritual and cultural life.
Abbey
The abbey precincts are entered through a fortress-like gate tower built from 1393 onwards, with notable terracotta reliefs of the school of Luca della Robbia. The conventual buildings, in brick, were erected in stages between 1387 and 1514, with some later restoration. The imposing church (early 15th century; remodeled in Baroque style) has beautiful choir-stalls.
Things to See
Buonconvento
The little town of Buonconvento was established in the 14th century on the site of the Roman Fort of Percanna on the Via Cassia, and is surrounded by the 14th century walls of Sienese type. It has a fine 15th century parish church (Santi Pietro e Paolo), containing some good paintings, and an excellent picture gallery with works of the medieval Tuscan schools. The Emperor Henry VII died in the town in 1313.
Frescoes 
On all four sides of the great cloister of the monastery of Monte Oliveto Maggiore are frescoes of outstanding quality. The cycle consists of 35 scenes from the life of St Benedict of Nursia (c. 480-547), founder of the Benedictine Order; nine of the paintings (1479 onwards) are by Luca Signorelli, the others (1505 onwards) by Sodoma. On request a monk will explain the various scenes and the legends on which they are based. Other features of interest in the abbey are the library, the pharmacy and the chapter-house. These rooms can be seen only in the company of a monk.
