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

Legend has it that the abbey was founded after a dream by the wealthy landowner Giovanni Tolomei. In a dream, the Sienese nobleman saw a vision of a silver ladder rising to 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. Specifically, the three decided to join the Benedictine order, following the famous rule “Ora et Labora”.

To this day, the abbey's architecture reflects the traditional layout of Benedictine monastic complexes, which usually include 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 starts at the entrance, where you'll pick up your audio guide. This will take you on a journey to discover the secret places of the monastery, including the beautiful church, built in the 1400s but later transformed in the 18th century in Baroque and Rococo style. 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 Sodoma. The vivid tones and highly detailed images of these masterpieces do a great job of telling the story of life, characters, and landscapes of the 1400s.

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'll wrap things up in the scenic underground cellar, where you'll find precious aged barrels and wines handcrafted by the monks, as well as the award-winning best extra virgin olive oil in the Tuscany Region.

Inside the monastery grounds, there's a wonderful garden where you can get in touch with nature by walking, meditating, or reading. It's a place that restores the soul, so we highly recommend a visit. You'll also find small, pretty chapels shrouded in mysticism.

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

• 3 wines from the monastic tradition
• 1 extra virgin olive oil of their production, served in dedicated glasses
• Platter of Tuscan cold cuts and cheeses, served with bread and breadsticks

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