If ever Bacchus blessed a landscape, it was the hilly terrain south of Siena. The dry clay soil is ideal for those Mediterranean plants: grapevines and olive trees. Two of Italy’s mightiest red wines hail from these parts – Brunello di Montalcino and Vino Nobile di Montepulciano. And where even the vines can’t take hold, grasslands thrive to provide rich grazing for sheep on the hills around Pienza, their milk producing the finest pecorino cheeses. Charming medieval hill towns, cypress-lined roads, isolated monasteries, Renaissance palazzi, Sienese School altarpieces and Etruscan tombs complete the picture.
Tourist office: Piazza Don Minzoni 1; 0578 757 341 • www.prolocomontepulciano.it
This hill town (see Montepulciano) boasts buildings by major Renaissance architects and Tuscany’s second greatest wine, Vino Nobile (see Marchesi de’ Frescobaldi (Chianti Rufina/Montalcino)). Via Gracciano nel Corso is lined with Renaissance palazzi by the likes of Vignola and Antonio da Sangallo the Elder. Also look out for Palazzo Bucelli (No. 73), its base embedded with Etruscan urns. The Piazza Grande is flanked by palaces by Sangallo, the town’s Duomo and the Palazzo Comunale, which is Michelozzo’s tribute to Florence’s Palazzo Vecchio. Inside the Duomo are Michelozzo sculptures that once formed a single tomb, while the gilded altarpiece is Taddeo di Bartolo’s Sienese Gothic masterpiece of 1401. Set on a patch of grass below the town walls is Sangallo’s geometrically precise church of Tempio di San Biagio (1518–34), the best example of the High Renaissance trend towards Greek Cross churches.
Tourist office: Piazza del Popolo; 0577 849 331 • www.montalcino.net
The hometown (see Montalcino) of Brunello (see Marchesi de’ Frescobaldi (Chianti Rufina/Montalcino)), Tuscany’s mightiest wine, is a small but proud burg, with an excellent wine shop in the 14th-century fortezza,, a split-level main square and a 1292 tower. The Museo Civico e Diocesano houses paintings by Simone Martini, Sano di Pietro and Vecchietta, and polychrome wood statues by Francesco di Valdambrino.
Tourist office: Via delle Case Nuove 4; 366 248 6015; www.prolocopienza.it • Duomo: Piazza Pio II; open daily
This assemblage of buildings is a UNESCO World Heritage Site, and includes a retro-Gothic town hall, a bishop’s palace (now the Museo Diocesano with art by Bartolo di Fredi, Pietro Lorenzetti, Vecchietta and), a papal palace with great hanging gardens and a Duomo. Corso Rossellino, the town’s main street, is packed with wine and cheese shops.
Abbazia di Sant’Antimo: open 10:30am–1:30pm & 2–7pm daily
A French-style Romanesque abbey (see Sant’Antimo) church standing in a countryside setting. Concerts and spiritual workshops are also held here.
Tourist office: Via Porsenna 79; 0578 227 667 • www.prolocochiusi.it/en
Chiusi’s fine Museo Archeologico Nazionale Etrusco contains bucchero (black Etruscan earthenware), a few 2nd-century-BC painted funerary urns, bronzes and Canopic jars. Buy tickets to visit the Etruscan tombs in the valley, including the Tombs of the Lion, the Pilgrim and the Monkey. The 12th-century Duomo is covered in trompe l’oeil frescoes (1887–94) that look like medieval mosaics. The adjacent Museo della Cattedrale preserves 15th-century illuminated scores from the Abbazia di Monte Oliveto Maggiore. Meet here for guided visits to the tunnels of the Etruscan Labirinto di Porsenna.
Monte Oliveto Maggiore • 0577 707 611 • Open 9:15am–noon & 3:15–5pm daily (summer: until 6pm)
On a cypress-covered hilltop in the Crete Senesi landscape of eroded clay and limestone bluffs is a 1313 Benedictine monastery (see Abbazia di Monte Oliveto Maggiore). Its cloister is frescoed with the Life of St Benedict, a masterpiece of High Renaissance narrative painting by Signorelli (the west wall’s eight scenes; 1497–8) and Sodoma (the other 25 scenes; 1505–8). Sodoma inserted a self-portrait in the third scene, his pet badgers at his feet.
Tourist office: Via Amos Cassioli 2 • www.prolocoasciano.it
With 14th-century walls and a travertine Romanesque Collegiata, Asciano stands amid the photogenic Crete Senesi hills. Palazzo Corboli, decorated with 14th-century civic frescoes, holds the town’s archaeological and sacred art collections, with panels by Ambrogio Lorenzetti and others. The Cassioli Museum is the only museum in Siena province dedicated to art from the Sienese School of the 19th century.
Little more than houses around a vast, Medici-built portico and basin steaming with naturally carbonated, volcanically heated waters. Lorenzo the Magnificent and St Catherine both bathed here, but sadly the old basin is no longer in use.Today the thermal baths are run by the township and offer a range of therapies.
Tourist office: Via Dante Alighieri 33; 0577 899 728
A friendly little farming town that boasts amazing Romanesque carvings on the Collegiata’s trio of 12th-century portals. Spot many fantastical creatures, stacked arches, tiny telamons and thin columns “knotted” in the centre and resting on toothless lions. Inside is a Sano di Pietro altarpiece.
Tourist office (at the museum): Piazzale Garibaldi; 3207 874 422; www.terresiena.it/info/tourist-information-offices
The tiny historic centre shelters a good Museo d’Arte Sacra, holding Sienese School works by Duccio, Sano di Pietro and Matteo di Giovanni, who also left a Madonna and Child in the town’s 14th-century Santi Piero e Paolo church.
Contemplative Benedictines retreated to isolated countryside monasteries, but Franciscans and Dominicans were preaching orders, and favoured town centres and huge churches to draw the masses (most effective under the monk Savonarola, see Santa Croce). Most monks were scholarly, illuminating manuscripts and using their herbal knowledge to run pharmacies so successful that many are still in business today.
Start at 9am in Chiusi, at the Museo Archeologico Nazionale Etrusco. After learning about the Etruscans, head across the piazza to join a Labirinto di Porsenna tour. They leave every 40 minutes, so you might be able to squeeze in a 10-minute tour of the Museo della Cattedrale as well. Then retrieve your car and take the winding S146 to Montepulciano. Park at the base of town to stroll up Via Gracciano nel Corso (its name changes constantly), sampling wines along the way. Stop for lunch at the Liberty-style Caffè Poliziano (Via Voltaio nel Corso 27–29), which has served light meals with great countryside views since 1858.
After lunch, continue up the main street and pop inside the Gesù to admire Andrea Pozzo’s illusionary painted “dome”. Next head to the Piazza Grande (more wine shops) and then on to the Duomo. Then drive on to Pienza but just before hitting the S146, stop at Via dei Canneti at the edge of Montepulciano to see the Tempio di San Biagio (you can skip the bare interior). Pienza is a quick stop. After viewing the Duomo’s altarpieces (see Pienza’s Duomo) and the giant cracks from the settling of the cliff, tour Pope Pius II’s Palazzo Piccolomini. An alley next to the palazzo leads to Via Gozzante, a panoramic walkway out of town. Drive on to Montalcino. In summer, head to the fortress for sunset views from the ramparts; in winter, make your way to the historic Caffè Fiaschetteria Italiana in the main square.
Via del Teatro 1 • Open 10am–12:30pm & 2:30–6pm daily
These winemaker’s labyrinthine cellars are inside a Renaissance palazzo. The range includes Vino Nobile DOCG wines and a sweet Vin Santo.
Via di Collazzi 74 • Open 11am–6pm • Closed Wed
Leading winery (see Gattavecchi (Montepulciano)) with grotto-like cellars. It sells Vino Nobile wines as well as estate olive oil. There is a small tasting fee.
Corso Rossellino 16 • Open 9am–1pm & 3–7pm daily
Boutique with every kind of pecorino plus honey, pâtés and conserves.
Corso Il Rossellino, 67 • Open 9am–1pm & 3–7pm daily
Cast and wrought iron of great beauty in everything from bedsteads and candlesticks to fantastical chandeliers, all handmade the traditional way using hammer and anvil.
Piazzale Fortezza • Open Apr–Oct: 9am–8pm; Nov–Mar: 9am–6pm
The best selection of wine (and other goods) in town gorgeous setting in the airy remains of the medieval fortress.
Via dell’Opio nel Corso 8 • 0578 758 672
Unique but expensive gold jewellery, inspired by ancient museum pieces.
Vicolo di Voltaia 40 • Open 10am–7pm daily
A bit of everything handcrafted and Tuscan: leatherwork, wrought iron, copper pots and more.
Via dell’Opio nel Corso 64 • Open 10am–7pm daily
The Mazzetti family sells a range of beautiful hand-hammered copperware.
Via del Leone 16 • Open 9am–1pm & 2:30–7:30pm • Closed Wed in winter
One of Tuscany’s best wine shops, with a good selection at almost every price.
Via Gracciano nel Corso 22 • Open 9am–7pm Mon–Sat
Beautiful leather-bound books and albums, each individually crafted in their bottega using the best-quality vegetable-tanned leather.
Via della Madonnina 88 (near Montepulciano/Pienza) • 0577 669 668 • Closed Tue • €€€
Set in an 18th-century oil mill, La Chiusa serves creative Tuscan cooking using local, seasonal ingredients.
Via Soccorso Saloni 5 • 0577 848 167 • Closed Tue • €€€
A refined restaurant located in the hill town of Montalcino in Siena. It is known for its innovative cuisine as well as excellent wine cellar. Booking advised.
Via San Carlo 2–4 • 0578 748 606 • €
Enjoy simple, soulful southern Tuscan cooking alfresco. Try the pici with garlic tomatoes or the roast suckling pig.
Piazza Cinughi 12, Torrita di Siena • 0577 669 481 • Closed Wed, Thu L • €€
Oak-beamed ceiling, stone and brick walls and food steeped in the traditions of the Sienese countryside.
Via del Teatro 22 • 0578 717 086 • Closed Tue • €
This place is a shrine to steaks (bistecca) which are ordered by weight before being brought to the table for approval. They are then briefly cooked on the flamegrill. Tasty sides include baked pecorino cheese with pear.
Via San Biagio 15 • 0578 757 479 • Closed Wed • €€
Top-class Tuscan cuisine is created in this beautiful Renaissance building with vaulted terracotta ceilings. The service is impeccable.
Via Arunte 12 • 0578 20 260 • Closed Wed • €
This is the best eatery in a renowned culinary town. Try the pasta del lucumone (“Big King’s pasta”), a baked casserole of ham and three cheeses.
Piazza di Spagna 1 • 0578 749 092 • Closed Wed • €
Tiny osteria with great mixed platters of pecorino cheese and salamis and a secret-family-recipe salad dressing.
Via Porsenna 21 • 0578 21 006 • Closed Tue • €€
A cosy spot offering traditional southern Tuscan dishes such as pici with duck sauce and Florentine trippa.
Località Sbarchino 36 • 0578 21 403 • Closed Tue • €
Set close to Chiusi’s tranquil lake, which provides the fresh catch of the day, this informal restaurant offers a solid fish menu and a good wine selection.
18.216.186.164