Montepulciano, is built along a narrow limestone ridge and, at 605 m (1,950 ft) above sea level. The town is encircled by walls and fortifications designed by Antonio da Sangallo the Elder in 1511 for Cosimo I. Inside the walls the streets are crammed with Renaissance-style palazzi and churches, but the town is chiefly known for its good local Vino Nobile wines. a long, winding street called the Corso climbs up into the main square, which crowns the summit of the hill.

In July-August there is Cantiere Internazionale d'Arte, an arts festival created by the German composer Hans Werner Henze. In August there are two festivals: the Bruscello takes place on the 14th, 15th and 16th, when hordes of actors reenact scenes from the town's turbulent history. For the Bravio delle Botti, on the last Sunday in August, there is a parade through the streets followed by a barrel race and a banquet to end the day.

Via di San Biagio, 14 - Open daily

This beautiful church is on the outskirts of Montepulciano. Built of honey - and cream - colored travertine, it is Sangallo's masterpiece, a Renaissance gem begun in 1518. The project occupied him until his death in 1534.

Corso, 73 - Closed

The lower façade of the palazzo (1648) is studded with ancient Etruscan reliefs and funerary urns collected by its 18th-century antiquarian owner, Pietro Bucelli.

Piazza Michelozzo - Open daily

Michelozzo built the church in 1427, with an elaborate carved portal featuring the Virgin and child flanked by St. John and St. Augustine.

Piazza Grande, 1 - Open Monday - Saturday

In the 15th century, Michelozzo added a tower and façade to the original Gothic town hall. The building is now a smaller version of the Palazzo Vecchio. On a clean day, the views that can be seen from the tower are superb.

Piazza Grande - Closed.

The imposing 16th-century palazzo is next to the town hall and is currently undergoing restoration to the façade.

Piazza Grande - Open daily

The Duomo was designed between 1592 and 1630 by Ippolito Scalza. The façade is unfinished and plain, but the interior is Classical in proportions. It is the setting for an earlier masterpiece from the Siena School, the "Assumption of the Virgin" triptych painted by Taddeo di Bartolo in 1401.

Castelmuzio is situated 443 metres above the sea level and it is a typical medieval village documented since 1213: this is testified by the reminds of fortifications and especially the architectonical structure with the church and the square placed on the top of the hill. San Bernardino stopped here many times to preach.

Cited as far back as the year 714, it belonged to both the Aldobrandeschi family and the Abbey of the SS. Salvatore; it subsequently passed into the hands of the Republic of Siena. The town is a picturesque one, evocative with little paved streets which converge upon the Piazza del Vecchietta, (dedicated to Lorenzo Di Pietro, known, in fact, as "il Vecchietta"). The paving of this town square was realised with river pebbles enclosed by lines of bricks forming a sunburst pattern, its spokes leading towards a well made from travertine stone dating back to 1618. The most important religious building of Castiglione d' Orcia is the church la Chiesa dei Santi Stefano e Degna with its façade from the 1500's. At the highest point in town, one can still see remains of the original city wall which opens upon a view of the mountain Monte Amiata and upon the fortress Rocca a Tentennano. The fortresses' imposing tower, recently restored, may also be visited when the fortress is open to the public. While there on its summit, enjoy the breathtaking 360 degree panorama from Siena to Radicofani, from Montalcino to Pienza and Montepulciano, and from Monte Amiata to Monte Cetona. Moving along past the Rocca a Tentennano, one enters into the village below called Rocca d' Orcia. Here worth a visit are the churches, the Pieve di San Simone, the Chiesa della Madonna delle Grazie di Manno, and the little main town square holding a cistern said to date back to 1262. In the large area covered by the municipality, many other towns also deserve a mention: first there is Bagni San Filippo, a place known for its spa waters which gush out water at a temperature of 52 degrees centigrade (125° Fahrenheit) and which have deposited immense calcium deposits in the nearby Fosso Bianco ('White Ditch'). Then there is Campiglia d'Orcia, featuring an unusual historical centre spreading out like a fan beneath a rocky ridge and from which rises a fortress built in the year 973. Ripa d' Orcia, on the right side of the river, has one of the most evocative castles in the valley. At Vivo d' Orcia there is the Hermitage (l'Eremo, also called Contea), a palace built in the late Renaissance Age by the Camaldolensians and, upriver from town, hidden among chestnut trees, an attractive little Romanesque church (dell'Ermicciolo) with both the façade and the apse decorated with small columns.

Montefollonico, situated 462 metres above the sea level, in a dominant position of Valdichiana, was a strategic point for the Republic of Siena. It has Etruscan origins. The Romans called the people who worked the cloths "fullones", and for this reason the name of the village seems to mean place where the cloths are worked. The effiged squared in the village coat-of-arm indicate the worked and ironed cloths. It keeps the ancient walls, the Palazzo Pretorio and the Pieve of San Leonardo from the medieval structure. The town walls, along which there are seven cylindric towers, is opened by three doors: the Porta a Foolonica, the Porta del Triano and the Porta del Pianello (also called Porta Nova), the latter represents a typical example of military architecture.