The imposing Abbey of Monte Oliveto Maggiore in Asciano is an oasis of spirituality nestled in the picturesque Crete Senesi area.

Legend has it that the Abbey’s foundation was inspired by 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 up to heaven. Once the complex was built, Tolomei changed his name to Bernardo and retired to the abbey to lead a more spiritual life alongside the other nobles, Ambrogio Piccolomini and Patrizio Patrizi. Specifically, the three men decided to join the Benedictine order, following the famous rule “Ora et Labora” (Pray and Work).

To this day, the abbey’s architecture reflects the traditional layout of Benedictine monastic complexes, which typically consist of the following spaces:

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

Your 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 monastery’s hidden treasures, starting with the beautiful church, which was built in the 15th century but later renovated in the 18th century in the Baroque and Rococo styles. Dedicated to the sacred figure of the Virgin Mary, the church houses great artistic masterpieces, including a wooden choir with 125 stalls inlaid by Fra Giovanni da Verona and a finely inlaid lectern by Fra Raffaele da Brescia.

From the church, the tour continues to the Great Cloister, which features beautiful frescoes by Luca Signorelli and Antonio Bazzi, known as Il Sodoma. The vibrant colours and highly detailed images of these masterpieces effectively depict the life, people, and landscapes of the 15th century.

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

We conclude our tour in the spectacular underground cellar, which houses precious aged barrels and wines handcrafted by the monks, as well as the award-winning best extra virgin olive oil in the Tuscany region.

Within the monastery grounds, there is a beautiful garden where you can connect with nature by taking a walk, meditating, or reading, as it is a place that rejuvenates the soul, so a visit is highly recommended. The garden also features charming little chapels imbued with mysticism.

Your visit to the Abbey concludes with the exquisite “Mystic Abbey” tasting, which includes:

• 3 traditional monastic wines
• 1 sample of the monks' extra virgin olive oil, served in special glasses
• A platter of Tuscan cured meats and cheeses, served with bread and breadsticks

Monte Oliveto Maggiore Abbey has been named one of the TOP 20 destinations for 2025 by National Geographic.
Hotel pick-up and drop-off available on request (additional charge)