The imposing Abbey of Monte Oliveto Maggiore in Asciano is an oasis of spirituality located in the pleasant surroundings of the Crete Senesi.

Legend has it that the Abbey's origins lie in a dream experienced by the wealthy landowner Giovanni Tolomei. In fact, during a dream, the Sienese nobleman had a vision of a silver staircase rising towards the sky. Once the complex was built, Tolomei changed his name to Bernardo and retired to the abbey to lead a more spiritual life with the other nobles, Ambrogio Piccolomini and Patrizio Patrizi. In particular, the three decided to join the Benedictine order, following the famous rule “Ora et Labora”.

To this day, the architecture of the Abbey reflects the traditional layout of Benedictine monastic complexes, which are usually composed of the following spaces:

Church; Large cloister; One or more small cloisters; Chapter house; Library; Room used as a refectory.

The visit to the Abbey of Monte Oliveto Maggiore begins at the entrance, where you will be given an audio guide that will take you on a journey to discover the secret places of the Monastery, starting with the beautiful church, built in the 15th century but later transformed in the 18th century in the Baroque and Rococo styles. Dedicated to the sacred figure of the Madonna, the church includes great artistic masterpieces, including a wooden choir inlaid by Fra Giovanni da Verona with 125 stalls and a lectern finely inlaid by Fra Raffaele da Brescia.

From the church, the tour continues to the Great Cloister with the beautiful frescoes by Luca Signorelli and Antonio Bazzi, known as il Sodoma. The vivid tones and highly detailed images of these masterpieces are very effective in depicting the life, characters, and landscapes of the 15th century.

From the Cloister, the itinerary continues into the refectory, the chapter house, and then the large library, which houses books, manuscripts, and volumes of great value.

We conclude in the scenic underground cellar, where the precious aged barrels and wines handcrafted by the monks are kept, as well as the award-winning best extra virgin olive oil in the Tuscany Region.

Within the monastic area, there is a wonderful garden where you can be in contact with nature by walking, meditating or reading, as it is a place that rejuvenates the soul, so a visit is strongly recommended. There are also small, charming chapels steeped in mysticism.

The visit to the Abbey ends with the exquisite “Mystic Abbey” tasting, which includes:

• 3 wines from the monastic tradition
• 1 extra virgin olive oil produced by the monks, served in special glasses
• Platter of Tuscan cold cuts and cheeses accompanied by bread and breadsticks

The Abbey of Monte Oliveto Maggiore has been listed among the TOP 20 destinations for 2025 by National Geographic.
Hotel pick-up and drop-off available on request (extra)