Siena holiday guide

Siena also hosts Italy's most thrilling pageant. Twice a year—on July 2 and August 16¬—jockeys representing ten of the city's sixteen contrade (neighbourhoods) race horses bareback, and at breakneck speeds, around the Campo, competing for the famous Palio (a banner).

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

Art & architecture

Siena's streets tunnel around and below a succession of Gothic palaces, most built from local, burnt sienna brick. Its scallop-shaped central square, Piazza del Campo (or simply 'Il Campo') was laid out in the 12th century. It was later divided into nine herringbone-brick segments, to represent the wise government of the Nine, who ruled Siena in its Medieval heyday.

Sienese painters had a style all their own, quite separate from the Renaissance solidity popularized in its northern rival, Florence.

Painter Duccio di Buoninsegna (c. 1255–1318) is the acknowledged founder of the Sienese School. His iconic Maestà was echoed by a similar painting of the 'Virgin in Majesty' painted on the walls of the Palazzo Pubblico by follower Simone Martini in 1315. Siena's Medieval city government met in the adjoining room: painter Ambrogio Lorenzetti was commissioned to cover it in frescoes, to remind them of the civic virtues and warn against vice. Known as 'The Allegories of Good and Bad Government' (1338), it remains the greatest secular artwork of Medieval Italy. As well as its message (received loud and clear), it is scattered with minute details from everyday Sienese life in the 14th century.

Behind its massive (and massively elaborate) Gothic façade, Siena's Duomo (cathedral) is also stuffed with art treasures. Umbrian painter Pinturicchio frescoed the Libreria Piccolomini in the early 1500s. Its scenes tell the life story of Pius II, a Sienese humanist scholar who became pope.

Visit between mid-August and late October and you will also see the cathedral floor, decorated with elaborate Biblical scenes in inlaid marble by Sienese artists like Domenico Beccafumi and Matteo di Giovanni. The whole thing took two centuries to complete.

If you want to dig deeper into Sienese art history, the Pinacoteca Nazionale showcases some of the back catalogue of the city's great painters, including Duccio, the Lorenzetti brothers, and Francesco di Giorgio Martini. Among the exhibits are Beccafumi's original 'cartoons' (or sketches) for his contributions to the cathedral floor.

  • Don't miss

    Palazzo Pubblico, Piazza del Campo 1, tel. 0577/292226

    Duomo, Piazza Duomo, tel. 0577/286300, www.operaduomo.siena.it; closed Sunday mornings

    Pinacoteca Nazionale, Via San Pietro 29, tel. 0577/286143; closed Sunday afternoons and Monday afternoons

Eating and drinking

Sienese cooking is simple and hearty, and makes plentiful use of the Cinta Senese, a local breed of pig prized for its sweet, succulent meat. Even a simple 'steak' of Cinta is a taste experience, and nowhere grills it better than L'Osteria, an informal place a few minutes' walk from the Campo.

The Campo itself is not a great place to dine—restaurants here cater to the tourist euro. But nearby, Osteria Le Logge has slowly upgraded over the years from a dependable trattoria to a refined restaurant inside and outside an old pharmacy. Expect dishes like beef tongue with fig and mustard gelato. It's ideal for a special dinner.

If you plan to eat on the move, stop in at deli Gino Cacino, behind the Palazzo Pubblico. Gino will load you a roll with any of his carefully chosen counter produce. His pecorino cheese aged in olive oil is worth the journey here on its own.

Just south of the Arno, Da Cucciolo is a simple and traditional Pisan trattoria. You won't spot many tourists in here: the vibe (and prices) are totally local.

The Sienese keep their bakers busy—this is a city with a deadly sweet tooth. Cantuccini (hard, almond-flour biscuits) are traditionally served after dinner with a bottle of sticky-sweet vin santo wine. But cantuccini hail originally from the city of Prato; Siena's authentic equivalent are ricciarelli, made in the city for six or seven centuries. Sweeter still is the dense honey, fruit, and nut cake called Panforte (a small piece is usually enough). Panpepato is similar, but dusted with ground black pepper and other warming spices.

Panpepato is just one of the innovative flavours often made at Kopa Kabana, the city's best gelateria.

  • Don't miss

    L'Osteria, Via de' Rossi 79, tel. 0577/287592; closed Sundays

    Osteria Le Logge, Via del Porrione 33, tel. 0577/48013, www.osterialelogge.it; closed Sundays

    Gino Cacino, Piazza del Mercato 31, tel. 0577/223076, www.ginocacinosiena.it; closed Sundays (and from 2.30pm onwards every day)

    Kopa Kabana, Via de' Rossi 52, tel. 0577/223744, www.gelateriakopakabana.it; closed from mid-November to mid-February

Local towns and villages

Pretty Asciano lies 30km south-east of Siena—take the SS438 for spectacular views of the countryside and back towards Siena's towers on the horizon. The town's Palazzo Corboli is now an archaeological and museum that focuses on local finds and artworks. Its highlight is a room covered in allegorical frescoes representing the seasons.

Buonconvento, on the agricultural plains south of Siena, is a roadside walled town with a charming, laid-back atmosphere. Nearby, at the isolated, gloriously serene monastery of Monte Oliveto Maggiore, painters Luca Signorelli and Sodoma frescoed the Great Cloister with scenes that narrate the life story of St. Benedict.

  • Don't miss

    Museo Palazzo Corboli, Corso Matteotti 122, Asciano, tel. 0577/719524, www.museisenesi.org; closed Mondays

    Monte Oliveto Maggiore, Chiusure, tel. 0577/707611, www.monteolivetomaggiore.it

The ourdoors

South-east of the city, the hills of the Crete Senesi form one of Tuscany's most recognizable landscapes. Roads twist and wind along ridges, ducking around cypress trees and lonely farmsteads, then suddenly jerk left or right to avoid the deep scars in the clay cut by millennia of erosion.

It is a magical place to spend a day in the saddle: the SS438 to Asciano is especially photogenic—particularly in the early morning or late afternoon light—as is the road south from there towards San Giovanni d'Asso.

Shopping

Siena's centuries-old rep for craftsmanship survives; take a walk along Via Stalloreggi to see the few remaining artisans still working within the old city walls. Sator Print sells hand-painted cards, bespoke calligraphy and stationery, and small pieces of art created using Medieval techniques and materials, including tempera.

  • Don't miss

    Sator Print, Via Stalloreggi 72, tel. 0577/247478, www.satorprint.com

Museums

Opposite the cathedral, Santa Maria della Scala is a museum complex built inside the city’s Medieval hospital, which did not close to patients until the 1990s. The lunettes of its Pellegrinaio (‘Pilgrims’ Ward’) were decorated in the 1440s with frescoes depicting Medieval hospital life. Downstairs is a spooky chapel known as the Oratory of St. Catherine of the Night. It was here that Siena’s fervent patron, Saint Catherine, use to pray and sleep overnight when she was in the city.

If the Museo dell’Opera del Duomo had just one painting, it would still be worth visiting. Duccio di Buoninsegna’s massive Maestà shows the Madonna and child with saints gathered in adoration—it is easy to spot St. Paul (with sword) and St. John the Baptist (pointing at the child and wearing animal skins). On the rear, a series of enchanting small paintings recount stories from the Bible, cartoon-strip style. The Maestà is Siena’s most important artwork and, on the day Duccio finished it, was carried in triumph from his studio on Via Stalloreggi to its place on the cathedral high altar, where it stayed for two hundred years.

The museum also gives access to the top of the Facciatone, the face of a never-completed extension to the cathedral. It’s not one for vertigo sufferers or claustrophobes… but once you have navigated the steep, narrow climb, views down into the Campo and across the red rooftops to the hills beyond are epic.

The Palazzo Pubblico has more than just the frescoes of Lorenzetti and Simone Martini. It is also Siena’s Museo Civico, with sculpture by Giovanni Dupré and Jacopo della Quercia and walls painted by Siena’s other fine Medieval and Renaissance artists, including Vecchietta, Taddeo di Bartolo, and Matteo di Giovanni.

  • Don't miss

    Santa Maria della Scala, Piazza Duomo 1, tel. 0577/534571, www.santamariadellascala.com

    Museo dell'Opera del Duomo, Piazza Duomo, tel. 0577/286300, www.operaduomo.siena.it

    Museo Civico, Piazza del Campo 1, tel. 0577/292226

Siena map Siena Siena Siena Siena

Key contacts

The best resource for the maps and ideas for exploring the area is Siena's tourist office, at Piazza del Campo 56, tel. 0577/280551, www.terresiena.it, e. infoaptsiena@terresiena.it.

Airports

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

With its countless Madonnas, sinuous figures, and flamboyant gold-leaf decoration, Sienese art can be a little daunting to the first-time visitor. Before your trip, read Sienese Painting: The Art of a City Republic by Timothy Hyman (Thames & Hudson). It is written in an accessible style and will help you understand and enjoy Siena's peculiar painting traditions.

Best & Finds

  • For the appetite. La Locanda del Castello, San Giovanni d'asso 'a great little restaurant ...' 2009
  • For the occasion. The abbeys at Monte olivieto Maggiore and San Galgano
  • For the occasion. Palio di Siena
  • For the body. Buddha Spa, Sovicille
  • A different view. Ballooning in Tuscany