Itinerary in the Crete Senesi
4 min · 30 May 2023
The area south-east of Siena, known as the Crete Senesi, is an obligatory stop for anyone in Tuscany. The name derives from the clay that emerges from the ground and gives the landscape its characteristic grey-blue colour. The area, often described as a lunar landscape, is characterised by an expanse of gullies and biancane (produced by water erosion on clayey and sandy sediments) and is dotted with a few villages perched on hilltops, in an atmosphere of unusual beauty.
The road through the Crete Senesi is particularly impressive and curve after curve one can admire breathtaking landscapes that literally leave one speechless.
Starting from Siena, the first stop on the itinerary is the hill of Montaperti, the site of the historic battle fought in 1260 between the Ghibelline troops led by Siena and the Guelph troops led by Florence, also mentioned by Dante in the Divine Comedy. Here one can enjoy a wonderful view of the Crete. The next stop is Rapolano Terme, a small village on the hill ridge separating the Ombrone Valley from the Valdichiana. There are numerous travertine quarries in the area, due to the presence of sulphurous waters, which also feed the local thermal baths of San Giovanni and Antica Querciolaia. Things to see include: the 14th-century Porta dei Tintori (Dyers’ Gate); the Archpriest’s Church of Santa Maria Assunta, which houses valuable works of art; the Parish Church of San Vittore, dating back to the 11th century; and the Museum of the Ancient Grancia and Oil, which documents the history of the ancient fortified farms.
After a few kilometres, the itinerary reaches Asciano, an ancient Etruscan centre entirely surrounded by 14th-century walls. Its historical centre, of medieval origin, is rich in architectural testimonies of great value. Undoubtedly worth a visit: the Collegiate Church of Sant’Agata, in which several paintings can be admired, including a tondo by Sodoma depicting the Deposition of Christ; the Church of San Bernardino, in Gothic style; the Cassioli Museum, dedicated to 19th-century Sienese painting; and above all the Civic Museum of Archaeology and Sacred Art housed inside Palazzo Corboli. Leaving Asciano, one enters the more impervious area of the Crete, among hills mottled and deeply incised by gullies, partly covered by sparse thickets, which become thicker in the vicinity of the Abbey of Monte Oliveto Maggiore, the Romanesque-style monastic complex founded in the 14th century. Its greatest treasures can be admired in the large cloister, decorated with frescoes of the Stories of St Benedict by Luca Signorelli and Sodoma, one of the most important examples of Italian Renaissance painting.
A few kilometres from the abbey is the medieval village of Buonconvento, surrounded by 14th-century walls, overlooking the confluence of the Arbia and the Ombrone. Listed among ‘I Borghi più belli d’Italia’ (Italy’s most beautiful villages), it is a very pretty village where you can still breathe in a timeless atmosphere. The Palazzo Podestarile, with its 14th-century civic tower and two Gothic arches opening onto the façade; the Church of Saints Peter and Paul, dating back to the 12th century even if its current appearance is the result of 18th-century restoration; and the Val d’Arbia Museum of Sacred Art, which houses an extraordinary collection of works of sacred art from the area. The itinerary then continues to Monteroni d’Arbia, where the Grancia di Cuna, one of the best examples of medieval fortified farmstead; the 14th-century Church of Saints Jacopo and Christopher; and the Romanesque Pieve di San Giovanni Battista in the fortified village of Lucignano d’Arbia are worth a visit. From Monteroni d’Arbia, take the road to Siena that heads towards Asciano among hills, rises, crags and gullies: the best viewpoints are at Pievina and Vescona.


