In the village of Montepulciano visit Antonio da Sangallo's San Biagio, a wonderful Renaissance church. You can then spend time walking the streets and feel what it was like to live in the medieval period.


In Pienza, in the mid-15th century, Pope Pius II turned this out of the way hill town into a testing ground for the most advanced Renaissance ideas about urban planning. Take a morning to walk the streets before moving onto the next village.

San Gimignano

San Gimignano is a medieval town that owes its famous skyline to the rival families who tried to outdo each other by building taller and taller towers. Of the original 76 towers only 13 still survive today.


This hill town is a medieval oasis in the "Crete" desert, with many historical monuments. It has a Romanesque Basilica di Sant'Agata within the 15th century ramparts.

Bagno Vignoni

Besides being a pleasant little town set up like a terrace on the Orcia valley, it has a thermal water basin right in the middle of the town square. It is a popular spa town with both an official spa and outside stone culverts with thermal water running in the open.

Crete Senesi

The name comes from the "crests" of clay eroded over the centuries into a dramatic desert of parched hillocks. The area is home to some of the most remote vestiges of the Sienese heritage in the enchanting scenery of the Val d'Orcia area. This unique natural landscape has inspired countless poets, writers and painters. only 13 still survive today.


South of the "Crete" , this enchanting fortified hill town is well-known for its red Brunello wine. A wine cellar (Enoteca) in the castle offers local wines for tasting and purchase.


This enchanting little hill town just 15 km north of Siena has an almost intact circular 13th century fortification wall enclosing the village. It used to be part of Siena's defence system against Florentine attacks.

Monte Oliveto Maggiore

This 14th century Benedictine monastery stands on a rocky ridge near Asciano in a scenic park of traditional tuscan trees. The nave's choir stalls count among Italy's finest works of inlaid wood carvings.


The 12th century Benedictine abbey, 10 km south of Montalcino enjoys a delightful setting amid olive groves.Translucent onyx and alabaster in the bases of the columns give the nave a delicate light.

San Quirico d'Orcia

This fortified town 15 km east of Montalcino was a major stop for north european pigrims journeying to Rome in the Middle Ages. The amazing view of the Orcia valley can be enjoyed from Piazza della Libertà.