One of the most breathtaking sights in Asciano, between Montalcino and Sienna, is the Abbazia di Monte Oliveto Maggiore. It is located on a hilltop, immersed in a dark yet beautiful natural landscape, and is marked by a suggestive, mystical history. The Abbey of Monte Oliveto Maggiore is a large Benedictine monastery 10 km south of Asciano. Its buildings, which are mostly of red brick, are conspicuous against the grey clayey and sandy soil — the Crete senesi which give this area of Tuscany its name.

Following the Via Francigena, this itinerary commences in Montalcino, town where the Brunello di Montalcino, one of Italy's most famous wines, is produced. Positioned on the summit of a hill, Montalcino is an ancient town which jealously guards both its artworks and its history. The imposing Rocca di Montalcino, occupying a strategic position overlooking all potential access points, defended the town from attack for centuries. Amidst the narrow roads of the historic center, important works of architecture can be seen. The Church of Sant Egidio and the Church of Sant'Agostino were both built in the 14th century, whilst the cathedral, constructed on the site of an ancient 9th century house of worship, dates back to the neoclassical period.

The Abbey of Monte Oliveto Maggiore is located 36 km south of Sienna in the characteristic "badlands" landscape of the Crete Senesi. The Olivetan community traces its foundation to 1313 and Giovanni Tolomei - who took the religious name of Bernardo - along with two of his friends, from the noble families of Sienna, Patrizio Patrizi and Ambrogio Piccolomini.
The approval for the building of the monastery came with the Charta fundationis by Guido Tarlati, bishop of Arezzo (26 March 1319), and the monastery took the name of Monte Oliveto «Maggiore» so as to distinguish it from successive foundations (Florence, San Gimignano, Naples, etc.). Construction of the monastery began in 1393 and was completed in 1526, although the buildings were further modified during the Renaissance and the Baroque periods.
An imposing square tower with a drawbridge that was part of the original defences erected to protect the entire complex stands at the entrance to the Abbey. The courtyard of the abbey opens onto a broad avenue of cypresses. To the left is the botanical garden that supplied medicinal plants for the monks. A little further on is the fish pond designed in 1553 by Pelori and used by the monks to provide fish at those times of year during which the Benedictine rule forbade the consumption of meat.
The cypress avenue leads to the impressively austere, late-gothic church of the abbey, built between 1399 and 1417 by order of the Abbot Ippolito di Giacomo da Milano. The single nave interior has a cross plan. The fine carved wooden lector is by Raffaele da Brescia and the inlaid wooden choir stalls are by Fra’ Giovanni da Verona. The transept leads to the Chapel of the Sacrament, whose altar is adorned by an early 14 C wooden Crucifix. In 1772 the church was redecorated in the late-Baroque style by Giovanni Antinori.
The abbey has three 15 C cloisters, of which the most magnificent is the rectangular Chiostro Grande, constructed between 1426 and 1443. It is made up of two passages, one above the other, supported by columns. The portico is decorated with a fresco cycle by Luca Signorelli depicting the life of St Benedict, who began work on its 36 large scenes in 1497. The cycle was finished in 1508 by Sodoma. The Chiostro Centrale is composed of a portico that rests on polygonal columns that lead to the magnificent Refectory, decorated with frescoes by Fra’ Paolo Novelli.

Another masterpiece of religious architecture, the Abbey of Sant Antimo, is situated just a few kilometers from Montalcino. Legend has it that this splendid example of Tuscan Romanesque was built on the site of the votive chapel erected by Charlemagne so as to conserve the relics of Saint Sebastian and Saint Antimo.

Tuscany | The Abbey di Monte Oliveto Maggiore