Tour of the Famous Tuscan Abbey & Wine and Olive Oil Tasting in Asciano, Chianti

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

According to legend, the Abbey originated from a dream experienced by the wealthy landowner Giovanni Tolomei. 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” (pray and work).

To this day, the architecture of the Abbey reflects the traditional layout of Benedictine monastic complexes, which usually consist of the following spaces: Church, Large cloister, One or more small cloisters, Chapter house, Library, and 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 into a Baroque and Rococo style. Dedicated to the sacred figure of the Madonna, the church includes great artistic masterpieces, including a wooden choir stall carved by Fra Giovanni da Verona with 125 seats and a lectern finely carved by Fra Raffaele da Brescia.

From the church, the visit continues to the Chiostro Grande (Great Cloister) with beautiful frescoes by Luca Signorelli and Antonio Bazzi, known as Sodoma. The vivid colors and highly detailed images of these masterpieces vividly depict the life, characters, and landscapes of the 15th century. The itinerary continues to the refectory, the chapter house, and then the large library, which houses books, manuscripts, and volumes of great value.

We conclude in the spectacular underground cellar, where the precious aged barrels and wines produced by the monks are stored, 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 connect with nature by walking, meditating, or reading, as it is a place that restores the soul. A visit is highly recommended. There are also small, charming chapels shrouded in mysticism.

The visit to the Abbey ends with the exquisite “Mystic Abbey” tasting, which includes: 3 traditional monastic wines, 1 extra virgin olive oil produced by the Abbey, served in special glasses, and a platter of Tuscan cold cuts and cheeses accompanied by bread and breadsticks.

The Abbey of Monte Oliveto Maggiore has been included among the 25 TOP 2025 destinations by National Geographic.