
Abbadia San Salvatore is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 110 kilometres (68 mi) southeast of Florence and about 60 kilometres (37 mi) southeast of Siena, in the area of Monte Amiata.

Asciano is a comune and hill town in the province of Siena in the Italian region Tuscany. It is located at the centre of the Crete senesi between the river Ombrone and the torrent Copra, some 30 kilometres (19 mi) southeast of the town of Siena by rail.

The Bottini di Siena are a complex system of medieval underground aqueducts for the water supply of the city of Siena with a total length of 25 km. The system used to be the main water supply of the entire city of Siena until 1914 and nowadays continues to supply water to the fountains of Siena.

Buonconvento is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 70 kilometres (43 mi) south of Florence and about 25 kilometres (16 mi) southeast of Siena in the area known as the Crete Senesi.
Casole d'Elsa [ˈkaːzole] is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 50 kilometres (31 mi) southwest of Florence and about 25 kilometres (16 mi) west of Siena.

Castellina in Chianti is a comune (municipality) of c. 2,800 inhabitants in the province of Siena, in the Italian region Tuscany, located about 35 kilometres (22 mi) south of Florence and about 15 kilometres (9 mi) northwest of Siena. It is part of the Chianti Hills, between the valleys of the Arbia, Pesa and Elsa rivers.

Castelnuovo Berardenga is a comune (municipality) in the province of Siena in the Italian region Tuscany, located about 50 kilometres (31 mi) southeast of Florence and about 14 kilometres (9 mi) east of Siena. Since 1932 it is included in the Chianti wine-production area.

Castiglione d'Orcia is a comune (municipality) in the Province of Siena in the Italian region of Tuscany, located about 90 kilometres (56 mi) southeast of Florence and about 40 kilometres (25 mi) southeast of Siena, in the Val d'Orcia, not far from the Via Cassia.

Cetona is a town and comune in the southern part province of Siena, Tuscany, in an area where Umbria and Lazio meet.

Chianciano Terme is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 90 kilometres (56 mi) southeast of Florence and about 50 kilometres (31 mi) southeast of Siena. It is located between the Valdichiana and the Val d'Orcia.
Chiusdino is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 70 kilometres (43 mi) south of Florence and about 30 kilometres (19 mi) southwest of Siena.

Chiusi is a town and comune in province of Siena, Tuscany, Italy.

Colle di Val d'Elsa or Colle Val d'Elsa is a town and comune in the province of Siena, Tuscany, central Italy.

Gaiole in Chianti is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 40 kilometres (25 mi) southeast of Florence and about 15 kilometres (9 mi) northeast of Siena. Forbes named it number one in its list of "Europe's Most Idyllic Places To Live."

Montalcino is a hill town and comune in the province of Siena, Tuscany, central Italy.

Montepulciano is a medieval and Renaissance hill town and comune in the Italian province of Siena in southern Tuscany. It sits high on a 605-metre (1,985 ft) limestone ridge, 13 kilometres (8 mi) east of Pienza, 70 kilometres (43 mi) southeast of Siena, 124 kilometres (77 mi) southeast of Florence, and 186 kilometres (116 mi) north of Rome by car.

Monteriggioni is a comune in the province of Siena in the Italian region of Tuscany. It borders on the communes of Casole d'Elsa, Castellina in Chianti, Castelnuovo Berardenga, Colle di Val d'Elsa, Poggibonsi, Siena and Sovicille. The town is architecturally and culturally significant; it hosts several piazzas, and is referenced in Dante Alighieri's Divine Comedy.

Monteroni d'Arbia is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 60 kilometres (37 mi) south of Florence and about 13 kilometres (8 mi) southeast of Siena in the area known as the Crete Senesi. It takes its names from the Arbia torrent, a tributary of the Ombrone River.
Monticiano is a town and comune on the right bank of the Val di Merse, Province of Siena, Tuscany, central Italy. The town is situated on the Colline Metallifere.
Murlo is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 70 kilometres (43 mi) south of Florence and about 20 kilometres (12 mi) south of Siena.

Piancastagnaio is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 110 kilometres (68 mi) southeast of Florence and about 60 kilometres (37 mi) southeast of Siena.

Pienza is a town and comune in the province of Siena, Tuscany, in the historical region of Val d'Orcia. Situated between the towns of Montepulciano and Montalcino, it is considered the "touchstone of Renaissance urbanism".

Poggibonsi is a town in the province of Siena, Tuscany, central Italy. It is located on the river Elsa and is the main centre of the Valdelsa Valley.

Radda in Chianti is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 35 kilometres southeast of Florence and about 15 km north of Siena.

Radicofani is a comune in the Province of Siena in the Italian region Tuscany, located in the natural park of Val d'Orcia about 110 kilometres (68 mi) southeast of Florence and about 60 kilometres (37 mi) southeast of Siena.

Radicondoli is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 60 kilometres (37 mi) southwest of Florence and about 25 kilometres (16 mi) southwest of Siena.
Rapolano Terme is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 60 kilometres (37 mi) southeast of Florence and about 20 kilometres (12 mi) east of Siena in the area known as the Crete Senesi.
San Casciano dei Bagni is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 110 kilometres (68 mi) southeast of Florence and about 70 kilometres (43 mi) southeast of Siena.
San Gimignano is a small walled medieval hill town in the province of Siena, Tuscany, north-central Italy. Known as the Town of Fine Towers, San Gimignano is famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses, which, with its hilltop setting and encircling walls, form "an unforgettable skyline". Within the walls, the well-preserved buildings include notable examples of both Romanesque and Gothic architecture, with outstanding examples of secular buildings as well as churches. The Palazzo Comunale, the Collegiate Church and Church of Sant' Agostino contain frescos, including cycles dating from the 14th and 15th centuries. The "Historic Centre of San Gimignano" is a UNESCO World Heritage Site. The town also is known for saffron, the Golden Ham, and its white wine, Vernaccia di San Gimignano, produced from the ancient variety of Vernaccia grape which is grown on the sandstone hillsides of the area.
San Quirico d'Orcia is a comune (municipality) of about 2,500 inhabitants in the Province of Siena in the Italian region Tuscany, located about 80 kilometres (50 mi) southeast of Florence and about 35 kilometres (22 mi) southeast of Siena inside the Valdorcia landscape. It is named in honor of Saint Quiricus.
Sarteano is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 100 kilometres (62 mi) southeast of Florence and about 60 kilometres (37 mi) southeast of Siena.

Siena is a city in Tuscany, Italy. It is the capital of the province of Siena.

Sinalunga is a town and comune in the province of Siena, in the Tuscany region of central Italy.
Sovicille is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 60 kilometres (37 mi) south of Florence and about 10 kilometres (6 mi) southwest of Siena.

Torrita di Siena is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 80 kilometres southeast of Florence and about 40 km (25 mi) southeast of Siena.
Trequanda is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 70 kilometres (43 mi) southeast of Florence and about 30 kilometres (19 mi) southeast of Siena.