City Information

The hill towns and valleys south of Siena comprise perhaps Tuscany's most enchanting and downright picturesque region. It's a land of medieval castles guarding narrow road passes, isolated farmhouses sitting atop long, eroded limestone ridges, clusters of cypress and ribbons of plane trees against a bucolic backdrop, and thermal spas enjoyed by both the Medici and the modern proles. The region has a few small patches of forest on the steeper slopes of its river valleys, but most of it has been landscaped to a human scale over thousands of years, turning the low, rolling hills into farmlands and vineyards that produce Tuscany's mightiest red wines.

Southern Tuscany's cities are textbook Italian hill towns. Chiusi dwells deep in its Etruscan roots, still remembering a time when King Lars Porsena was one of the few leaders of the Etruscan confederation who had the audacity to take on Rome. Roman settlements like Montalcino and Montepulciano grew into medieval cities and today produce two of Italy's top red wines, the powerhouse Brunello di Montalcino and the noble Vino Nobile di Montepulciano. And the gemlike village of Pienza, famed for its pecorino sheep's cheese, shelters within its tiny ring of walls a Renaissance core of the most perfect proportions and planning.

Much of the area is filled with the expansive and beautiful Val d'Orcia -- many people's idealized picture of Tuscany because well over half the souvenir-stand postcards and cover shots of coffee-table books with "Tuscany" in the title were snapped here. From many parts of it, especially the zone around Montalcino and Pienza, you can see the broken tooth of the Rocca d'Orcia. From the 11th to the 14th century, the castle was a stronghold and strategic watchtower of the Aldobrandeschi clan, formidable toll collectors along the Francigena pilgrim road through these parts. The castle juts from its crag to the south, still keeping an eye on its valley.

En Route to Montalcino -- The SS438 leads 26km (16 miles) from Siena to Asciano, a small town still partially girded by its 1351 Sienese walls. The tourist office is at Corso Matteotti 18 (tel. 0577-719-510 for all sights), open Tuesday through Saturday from 10am to noon and 3 to 6pm, Sunday from 10am to noon.

The 14th-century Palazzo Corboli, Corso Matteotti 122, frescoed by Ambrogio Lorenzetti or his school, now houses two museums. The Museo d'Arte Sacra contains good early Sienese works; don't miss the Madonna by Segna di Bonaventura, a 1410 Annunciation carved in wood by Francesco di Valdambrino, and Ambrogio Lorenzetti's St. Michael altarpiece. The Etruscan collections were gleaned from tombs discovered in the area and include a couple of nicely painted 3rd- to 5th-century B.C. vases, funerary urns, and the standard pile of pottery bits. The palazzo is open Tuesday through Sunday from 10am to 1pm and 3 to 7pm. Admission is 4.13€ ($4.75) adults, 2.58€ ($2.95) for students and seniors over 65 (yes, the prices are odd, but very precise).

At the Museo Cassioli, Via Mameli 36, with a collection of late-19th- and early-20th-century art by a local artist and his son (open by request at the number above). A block and a half up the street, at Corso Matteotti 80, is the Antica Farmacia Francini Naldi, a 19th-century pharmacy where you can view the Roman mosaic floor in the basement if you ask politely. At the opposite end of the block stands the Romanesque and Gothic Collegiata, built of travertine between the 10th and 13th centuries. The interior has, unusually, three apses and a 15th-century Sienese-school crucifix over the altar.

Asciano is surrounded by biancane, land formations where erosion has left emerald lawns like toupees atop knobby white hills. These blend to the south with the crete senese, a similarly eerie landscape of eroded clay and Jura limestone hillsides with farmhouses perched atop deep washed-out gullies and cypress crowded along sheer ridges. In the center of these weird badlands, accessible by a couple of side roads out of Asciano, the abbey of Monte Oliveto Maggiore (tel. 0577-707-611 or 0577-707-017; www.ftbcc.it/monteoliveto) is hidden in its own womb of cypress.

Founded in 1313 by a group of wealthy Sienese businessmen who wanted to retire to a contemplative spiritual life, the redbrick monastic complex was built by the early 15th century. The Olivetans were an order trying to restore some of the original simplicity and charity of the Benedictine rule, and the monks cared for victims during the 1340s Black Death outbreak. What draws most casual visitors today is the 36-scene fresco cycle by Luca Signorelli and Sodoma, one of the masterpieces of High Renaissance narrative painting and Sodoma's greatest work. When you arrive, pass under the gate tower with its small cafe and walk through the cool woods for about 5 minutes to the bulky brick of the complex. The entrance to the monastery is around to the right, but first pop into the church to see some gorgeous choir stalls inlaid by Giovanni da Verona (1505). A doorway, not always open, leads into the chiostro grande and puts you right at the frescoes' start. Otherwise, leave the church by the front and enter the Great Cloister through the doorway to your left.

Signorelli started the job of illustrating the Life of St. Benedict here in 1497. He finished nine of the scenes before skipping town the next year to work on Orvieto's Duomo. Antonio Bazzi arrived in 1505 and finished the cycle by 1508 in his own inimitable style. Bazzi was known as "Il Sodoma," a derogatory nickname that Vasari suggests was due to Bazzi's predilection for young men. Sodoma was married at least three times, however, and may have had in the neighborhood of 30 children. On the third, or west wall, are the Signorellis. (Scene 20, Benedict Sending Mauro to France and Placido to Sicily, is an interlude by Il Riccio.) Scenes 21 to 28, starting with Fiorenzo's Death, are by Signorelli (his last work, no. 29, was destroyed when a door was installed). Sodoma did most of the rest of the painting in this part of the monastery, including the grotesques and monotone details on the pilasters between the scenes and two fine separate frescoes: a small Christ at the Column and St. Benedict Confers the Rule on the Olivetans, both in the passage leading from the church. Monte Oliveto is open daily from 9:15am to noon and 3:15 to 5:45pm (until 5pm from the last Sun in Oct to the last Sun in Mar). Admission is free.

The SS451 leads 9km (6 miles) to the Via Cassia SS2 and Buonconvento (tourist info at the museum). Hidden within a ring of industrial suburbs is Buonconvento's medieval core and an excellent small museum of Sienese-school art, the Museo d'Arte Sacra, Via Soccini 18 (tel. 0577-807-181), with works by Duccio, Sano di Pietro, Andrea di Bartolo, and Matteo di Giovanni. It's open Easter through October Tuesday through Sunday from 10:30am to 1pm and 3 to 7pm, November through Easter Saturday and Sunday from 10:30am to 1pm and 3 to 5pm. Admission is 3.10€ ($3.60). Before leaving town, drop by the 14th-century Santi Pietro e Paolo, where you'll see a pair of Madonna and Child paintings, one with saints by Pietro di Francesco Orioli and one without by Matteo di Giovanni. Just south of Buonconvento on the right is the turnoff for Montalcino.