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Montepulciano holiday guide

Written by Donald Strachan, Italy specialist and Travel Writer for The Guardian.

  • Don't miss

    The view across rolling hills and vines from the roof of Montepulciano's Palazzo Comunale

    A tasting session or two with one of Tuscany's great red wines, Vino Nobile di Montepulciano

    Scrambling in and around the Etruscan tombs close to Sarteano and Chiusi

Art & architecture

The stiff, uphill walk from the Porta al Prato along the length of Montepulciano's Corso (main street) is one of the most genteel of any Tuscan hill-town. After a truce with Florence, some of the Renaissance's finest architects built palaces for local notables.

Architect Vignola designed the Palazzo Avignonesi in High Renaissance symmetry. It is right opposite a column topped with the Marzocco, traditional symbol of Florence. Andrea Pozzo, Michelozzo and Giuliano da Sangallo (Antonio's nephew) also contributed to Montepulciano's handsome main drag. It is a treat for architecture fans.

At Montepulciano's highest point, stand right in the middle of Piazza Grande to soak up a 360-degree architectural panorama. On the west side of the square, the Palazzo Comunale was built in the late 1300s then revamped in 1424 by one of the Medici's favourite architects, Michelozzo, in homage to Florence's Palazzo Vecchio.

The name most associated with Montepulciano's appearance is Antonio da Sangallo the Elder. The Florentine architect settled here for the last fifteen years of his life, designing several buildings and palaces before his death in 1534. The porticoed building on the north side, with a façade completely in honey-coloured travertine (a type of limestone) is Sangallo's Palazzo Nobili-Tarugi. The adjacent well, sporting the gryphon (symbol of Montepulciano) and the Marzocco (representing Florence), is also by Sangallo.

On the east side of the piazza is the Palazzo Contucci, occupied by a famous wine-making family (there is a tasting cantina in the basement).

On the south side is the underwhelming (in fact, never finished) façade of the Cattedrale di Santa Maria Assunta, Montepulciano's 16th-century cathedral. The dark interior is illuminated (literally) by a dazzling gold altarpiece in the Sienese style, by Taddeo di Bartolo (1401). It shows the Assumption (raising to heaven) of the Virgin Mary.

Just outside the town gates, a stiff downhill walk from Piazza Grande, is Sangallo the Elder's masterpiece, and one of the most photographed churches in Tuscany. Fronted entirely in travertine, San Biagio is designed on a perfect Greek cross pattern, and dedicated to St. Blaise, an Armenian doctor martyred in the 4th century.

  • Don't miss

    Palazzo Avignonesi, Piazza Savonarola

    Cattedrale di Santa Maria Assunta, Piazza Grande, tel. 0578/71951

    Tempio di San Biagio, Via San Biagio

Eating and drinking

If you like to eat—and especially if you have a passion for great ingredients served simply, rather than elaborate 'cuisine'—then this is the right part of Tuscany for you.

Meat is the main event on most menus—typically beef. Nowhere is it treated with more reverence than at Osteria Acquacheta. The raw flesh is brought to your table for approval, then cooked (briefly… it's rare or nothing here) over the flamegrill. The real magic is the ingredients: all locally sourced, all seasonal, and all prepared in-house every morning. And you won't believe the price. Seating is cramped, essentially communal, so this isn't a place for a romantic meal. But it is a food experience you won't quickly forget.

Equal care is taken with the produce at A Gambe di Gatto—owners Emanuel and Laura even close the place down each winter so they can travel in search of new ingredients. Dishes mix traditional and modern Tuscany, and are presented with flair. The wine list is expertly chosen, too, mostly from small Tuscan producers—you'll be offered a (free) tasting before you dine. The kitchen is open all day, so if you are travelling with kids they can accommodate unusual eating times.

In nearby Pienza, La Taverna di Re Artù makes the perfect day-trip lunch stop. It is a wine bar, so the menu is limited, but the tasting plates of local salami—around €8 and loaded enough for two to share—or bruschetta are always tasty.

Out in the sticks, in Monticchiello, pole position is the panoramic terrace at Osteria La Porta. The menu is classic Tuscan all the way, with regional speciality pasta pici (thick, uneven, hand-rolled spaghetti) sure to feature in Tuscan ragù sauces made with duck or boar. Mains are big on meat, too (guinea fowl, beef, and spicy stew peposo), plus there are usually truffles and porcini mushrooms in season. Book ahead for a memorable meal.

Then there's the wine—it is the Sangiovese grape that really put Montepulciano on the map. Vino Nobile di Montepulciano is one of Tuscany's great red wines, rich and soft and grown mainly on the lands east and north-east of the town. It is recognized by DOCG status—Denominazione di Origine Controllata e Garantita, the highest grade of Italian wine.

In Montepulciano itself, Gattavecchi sells a range of wines from everyday drinking reds to small-batch, concentrated Vino Nobile labels such as their Parceto, from its tasting room next to the church of Santa Maria dei Servi. Ask to see the cellar downstairs, where a simple, tiny underground chapel has been carved out of the tufa rock. Intriguingly, this little room sits right below the neighbouring church, which used to be a Servite convent. Multi-wine tastings start from €10 per person.

Gattavecchi's cool, vaulted dining room and outdoor terrace also host La Cucina di Lilian, an informal kitchen that zeroes in on ingredients from the hills around Montepulciano. Expect well-prepared Tuscan standards when it comes to pasta courses, and secondi that get right to the heart of la cucina poliziana, with dishes such as roast pork with almond cream. Prices are keen, around €10 for a main course.

The countryside is dotted with small cantinas happy to see visitors and offer tours and tastings. The best way to organize a wine-tasting day out is to visit or contact the Strada del Vino Nobile. Staff can advise on producers and routes to suit your taste and budget. The office in Piazza Grande issues maps and wine-tasting ideas.

  • Don't miss

    Osteria Acquacheta, Via del Teatro 2, tel. 0578/717086,; closed Tuesdays

    A Gambe di Gatto, Via del Opio nel Corso 34, tel. 0578/757431; closed between January and March (approximately)

    La Taverna di Re Artù, Via della Rosa 4, Pienza; closed Thursdays

    Osteria La Porta, Via del Piano 1, Monticchiello, tel. 0578/755163,; closed Thursdays and for the last three weeks in January

    Gattavecchi and La Cucina di Lilian, Via di Collazzi 74, tel. 0578/757110,

    Strada del Vino Nobile di Montepulciano, Piazza Grande 7, tel. 0578/717484,; email on for local wine-touring advice and ideas

Local towns and villages

Tiny Pienza, 13km west of Montepulciano, is such a perfect miniature model of Renaissance architecture that its entire centre is recognized by UNESCO, for the "new vision of urban space" it represented in the mid-1400s. The focus is Piazza Pio II, named after the pope (Pius II) who was born here and later commissioned Florentine architect Bernardo Rossellino to convert his home village into a model Renaissance town.

In truth, Rossellino never got much further than the main piazza. In the process he left a Duomo (1462) with handsome, regular blind arcades and niches on the façade. Unusually, the works Pius II commissioned for the interior are still in place—four hybrid Gothic-Renaissance altarpieces by leading Sienese painters, including Vecchietta and Matteo di Giovanni.

The adjacent Palazzo Piccolomini is Rossellino's masterpiece, a perfectly proportioned palace with hanging gardens with one of the best views in Tuscany—right down the entire Val d'Orcia. You can see the inside and gardens on a one-hour guided tour.

Sarteano, a pretty 21km drive south-east of Montepulciano, is a quiet town, well off the standard southern Tuscan itinerary. The collection at its small Museo Civico focuses on a rich crop of finds from the Etruscan period, most unearthed in the hills surrounding the town.

On Saturdays only, you can visit the Tomba della Quadriga Infernale, an Etruscan tomb in the Pianacce complex just outside town. Only discovered in 2003, the tomb is 19m long with walls still covered in frescoes that date to the 4th century BC, including a Demon Charioteer that is unique in Etruscan art. The preservation of the pigments is extraordinary; to see it, it is essential to book ahead by calling the museum or emailing The frescoes are so precious that numbers are seriously limited; reserve well ahead. If you can't make it on a Saturday, there is a decent reconstruction of the tomb's walls in the basement of the Museo Civico.

Chiusi, 23km south-east of Montepulciano, is another town with an important Etruscan heritage. As Clusium, or Clevsin, it was one of the most important members of the Etruscan alliance. The so-called Labirinto di Porsenna is a network of tunnels under the main square that date to Etruscan times—the name comes from Lars Porsenna, an Etruscan king who fought Rome in the 6th century BC. The labyrinth was still in use a couple of millennia later, when private fire brigades used the Roman-era cisterna (well) as a water source.

Chiusi's Museo Nazionale Etrusco has one of the best Etruscan collections in Tuscany, including painted, Attic-style ceramics and cinerary urns galore. The museum ticket also includes admission to a tomb complex 3km north of the town centre. You can wander the subterranean corridors of the Tomba del Leone (Lion Tomb) and Tomba della Pellegrina (Pilgrim's Tomb), which date from the 5th and 2nd centuries BC, respectively.

Chianciano Terme, 11km south of Montepulciano, is known for its thermal waters, said to be beneficial for the liver. 'Spas' in Chianciano are medicinal, rather than pampering. The town is also linked with novelist and Nobel Laureate Luigi Pirandello, who set two novellas here. You can follow a marked trail of sites relating to his time in the area in the tiny, atmospheric Medieval village of Chianciano Vecchia, just north of the main 20th-century spa development. A balcony by the Medieval Torre dell'Orologio (clock tower) is a fine place to pause and admire the view.

  • Don't miss

    Duomo di Pienza, Piazza Pio II

    Palazzo Piccolomini, Piazza Pio II, tel. 0578/286300,; closed Mondays, and for the whole of the second half of November and from early January to mid-February

    Museo Civico Archeologico di Sarteano, Via Roma 24, Sarteano, tel. 0578/269261,; closed Mondays and open weekends only between November and March

    Labirinto di Porsenna, entrance via Museo della Cattedrale, Piazza Duomo 7, Chiusi, tel. 0578/226490; between four and eight tours a day run Tuesdays, Thursdays, and all weekend between January and March, daily otherwise (but often closed afternoons)

    Museo Nazionale Etrusco, Via Porsenna 17, Chiusi, tel. 0578/20177

The outdoors

The best perch for seeing the lie of the land around Montepulciano is the roof of the Palazzo Comunale, which is open to the public (as long as you don't mind a steep, tight climb). The views stretch as far as Monte Amiata. The 1,738m mountain, an extinct lave dome, towers over southern Tuscany.

There is another great view at Le Pianacce, an Etruscan tomb complex just outside the centre of Sarteano (signposted beside the road to Cetona). The tombs date to the 6th century BC, and most were raided long ago, so you are free to wander to get a sense of how the Etruscans buried their important dead, in tombs that slowly ramp down into the earth and travertine rock. If the tomb's inhabitants ever re-emerge from the underworld, they will be met right away with an unforgettable view that stretches over the vast trough of the Valdichiana.

  • Don't miss

    Palazzo Comunale, Piazza Grande, tel. 0578/757341


Craftsmanship is alive and well in southern Tuscany, and workshops all along Montepulciano's Corso make and sell from the premises. At the Laboratorio Mosaici Artistici, mosaic artist Albo Mazzetti creates elaborate landscapes, portraits, and local street scenes by hand. Nothing is cheap (think of the patience needed!), but they make stunning souvenirs.

Elsewhere on the Corso, you can browse leather shops, ceramics, olive oils, local honey, and wine in abundance, local painters and intarsia artists, and more.

Pienza also has an artisan rep, mainly for its cheese: pecorino di Pienza, a local hard, sheep's milk cheese. Delis along Corso Rossellino sell it in various staged of maturity: fresco (fresh, young), semi-stagionato (partly aged), and stagionato (aged). It is the perfect picnic cheese, and a good wedge of it tastes great in a simple roll with salami.

Enoteca di Ghino, in Pienza, has the best selection of local wines for miles around, especially at the upper end of the price range. There is usually informal tasting available at the shop counter.

  • Don't miss

    Laboratorio Mosaici Artistici, Via di Cagnano 4, tel. 0578/757272,

    Enoteca di Ghino, Via del Leone 16, Pienza, tel. 0578/748262,


It is only small but Montepulciano's Museo Civico can fill an hour of your time. Exhibits include painted terracottas by Andrea della Robbia, archaeological remains left by the Etruscans, and paintings dating to the Medieval period (mostly Sienese in style). The collection is housed inside the Palazzo Neri Orselli, a Sienese palazzo from the 14th century.

  • Don't miss

    Museo Civico di Montepulciano, Via Ricci 10, tel. 0578/717300,; closed Mondays all year, and open weekends only between November and February

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Key contacts

Montepulciano's tourist office is close to the main town gate, at Piazza Don Minzoni 1, tel. 0578/757341,, e. There is a small car park right outside the office… but you need to arrive early. It fills quickly.

There are also tourist offices at Pienza (Corso Rossellino 30, tel. 0578/749905), Chiusi (Via Porsenna 79, tel. 0578/227667,, Chianciano Terme (Piazza Italia 67, tel. 0578/671122,, and Sarteano (Corso Garibaldi 9, tel. 0578/265312).


Pisa (PSA - Galileo Galilei) is Tuscany´s international airport, located about 40 minutes´drive west of Florence. Florence (FRL - Peretola), north-west of the city, is a smaller airport receiving domestic and European flights.

If your villa is in southern or eastern Tuscany, one of Rome´s two airports may be a more practical option: Fiumicino (FCO) is the larger, for international flights; Ciampino (CIA) has a fewer facilities and caters to the discounters and smaller European airlines. Both are just off Rome´s ring road, the GRA, and convenient to all the motorways.

The little airport at Perugia (PEG - Sant´Egidio), in Umbria, is convenient fr eastern Tuscany and receives domestic italian flights and discout airlines from UK.

Insider tip

Approach Montepulciano from Pienza for a memorable view of San Biagio. As you round the final bend before the town, there it is: set away from Montepulciano's walls, with not a single other building to pollute the view of Renaissance perfection. Catch it as the afternoon shadows begin to lengthen, and the whole church appears to glow gold.

Best & Finds

  • For the appetite. Lillo Tatini, Panicale 'Great atmosphere and umbrian menu.' 2010
  • For the occasion. The Scoppio del Carro at Easter, Florence
  • For the mind. Museo Archeologico nazionale, chiusi
  • For the soul. Terme di Chianciano spa, chianciano terme
  • For the palate. Avignonese, montepulciano 'Wine tasting was excellent.' 2008