Abbey of Santa Maria in Monte Oliveto Maggiore

Strade di Siena > Tuscan Spring – Tuscan New Year’s Day > Itinerario

Abbey of Santa Maria in Monte Oliveto Maggiore – Asciano

This route leads us to a magical place in the Crete Senesi (Clays of Siena), called the “Accona desert” at the beginning of the fourteenth century, due to the inhospitable nature characterised by gullies, present on this hill located approx. 30 km from Siena. Nevertheless, this “desert” was transformed into an oasis of silence and contemplation by Giovanni Tolomei (1272-1348), a Sienese nobleman, very devoted to the Virgin Mary, who decided to retire to a hermit’s life in these places, choosing the name of Bernardo.

Today, Monteoliveto Maggiore is a guiding light of spiritualism and of artistic and cultural beauty, famous worldwide.

The route starts in Siena to then head towards Asciano, in the centre of the Crete Senesi, along the Via Lauretana, a tarmacked road that runs through landscapes of rare beauty, with elevation gains at times challenging.

From Asciano the road, always tarmacked, begins to climb towards Monte Oliveto Maggiore, passing through the most authentic part of these almost lunar landscapes. Before Monte Oliveto Maggiore, the small village of Chiusure is definitely worth a visit, perched on a hill from whose top one can enjoy a wonderful view.

From Monte Oliveto a pleasant descent begins towards Buonconvento, a fortified centre located along the ancient Via Francigena, from where, always along the Via Francigena, the itinerary returns to Siena, through a long stretch of basically flat dirt road.

The places of various artistic, cultural and religious interest are indicated in green on the map.

Cultural information and insights

In Monteoliveto Maggiore, devotion to the Virgin is testified not only by the dedication of the church to the Nativity of Mary (built between 1399 and 1417), but also by the presence inside the abbey of works of art with a Marian theme.

These include the fourteenth-century Majesty by Maestro di Monteoliveto (the oldest work preserved in the monastery), the large canvas placed above the main altar depicting the Nativity of the Virgin painted by Jacopo Ligozzi and commissioned by the Grand Duke in 1598, and by the same author we also have the Assumption of the Virgin. On the ceiling of the church we find an eighteenth-century fresco depicting the Vision of the silver staircase by Ermenegildo Costantini. In addition, in the vault of the chapel on the right we have a beautiful oil tondo depicting the Annunciation.

In the left transept of the church there is a very curious work, a simulacrum of Mary the Child, modelled in wax by Sister Chiara Isabella Fornari and donated to the Abbey in 1775.

On 8 September, feast of the Nativity of Mary, the simulacrum of Mary the Child is solemnly carried in procession around the abbey.

““With the co-participation of the Regional Council of Tuscany””