Montepulciano (10 km) is a charming and interesting town built on the slopes of a hill dominating the south-eastern part of Tuscany and the border with Umbria. The town is known as the Pearl of the Renaissance because of its many splendid 14th century “palazzi” and the Temple of San Biagio, one of the largest High Renaissance churches to have been built during the period. Montepulciano is famous for its fine red wines the best known being the Vino Nobile.

Pienza (25 km) is a small but elegant Renaissance town, the birthplace of Enea Silvio Piccolomini who became Pope Pius II. Piazza Pio II, designed and constructed by Bernardo Rossellini, is a noteworthy example of Renaissance town planning.
The Cathedral (Duomo) has an interesting classic façade in travertine stone.
To the right of the Duomo stands Palazzo Piccolomini, reminiscent of Palazzo Rucellai dell’Alberti in Florence.

Montalcino (46 km) is an enchanting town surrounded by imposing stone walls and situated on a lofty hill looking out over a countryside swathed in olive groves and vineyards. It is famous throughout the world for its fine red wines and in particular il Brunello one of Italy’s finest vintage wines.

Bagno Vignoni (25 km) is a charming Mediaeval spa town built high above a gorge through which runs the river Orcia. The piazza has a pool or vasca termale built during the Renaissance and filled with the hot waters of a sulphur spring.

Sarteano (7 km) originally a Stone Age settlement, Sarteano later became a flourishing Etruscan centre linked to Chiusi. Situated on a hilltop, the town grew up alongside its fine 10th century Castle. Two of the original town gateways still exist.

Cetona (15 km) originally an Etruscan village, the typical mediaeval town developed in a spiral around its castle between 1207 and 1214. In the surrounding area there are 25 caves in which the remains of prehistoric settlements dating back 40,000 years have been found.

Monticchiello (6 km), in Etruscan and Roman times the town was at the centre of an important crossroad connecting towns and villages in the area. In contrast to the distinct Renaissance atmosphere of nearby Pienza, Monticchiello has a decidedly Mediaeval feel to it. The sturdy walls and the castle tower dominating the town are signs of the town’s intense history as a fortified outpost of the Republic of Siena.

Chiusi (15 km) was an extremely important Etruscan city and the large number of artefacts to be found in its noteworthy museum plus the vast necropolis that surrounds the town are evidence of this.

San Quirico d'Orcia (31 km) is a mediaeval town dating back to the 8th century and built along the Via Francigena, an ancient pilgrim route.
During the 13th century, the town walls were extended and hospices were built to accommodate pilgrims on their journey to Rome. The Romanesque collegiate church was built in the 12th century and its imposing doorway is the best example of Lombard architecture to be found in the province of Siena.

Radicofani (15 km), the town is dominated by the fortress overlooking the valley of the river Paglia. The fortress was built during the high mediaeval period and became an important military outpost and was subsequently enlarged several times due to its strategic position. It was a stopping place for pilgrims and other travellers making their way southwards along the Via Francigena towards Rome. They could admire the magnificent view from the ruins of the fortress evoking recollection of the legendary figure Ghino di Tacco.