The Best Of: Siena

Siena's 15th-century republican experiment, its affluence as the home of banking, and its outstanding patronage of the arts forged a city that, for today's visitor, is packed with treasures.

Siena's 15th-century republican experiment, its affluence as the home of banking, and its outstanding patronage of the arts forged a city that, for today's visitor, is packed with treasures. It is also famous for the Palio, the dangerous and glamorous bare-backed horse race that is run round the irregularly curved slopes of the Campo. But it is through painting that this miniature city has exerted its influence worldwide. Today, the vivid livery of the Palio, shop windows stuffed with art and covetable fashion, and the strawberry blond sunlight on Siena's calm frontages make for colourful walks through traffic-free streets and, out of season, largely deserted alleys.

Best hotel

You virtually need planning permission to put your hat on in Siena, so the extraordinary restoration of the Grand Hotel Continental (00 39 05 77 56 011; www.royaldemeure.com), once a fine palace in the Banchi di Sopra, one of two fashionable streets that scoop through the centre of the city, was a considerable achievement. Rooms include a totally frescoed suite, with views of the Duomo and of the church of San Domenico. There is also a turret with rooms on two floors and 360-degree views, and some of the eaved rooms have balconies. The Salle delle Feste is a frescoed public room on the first-floor, alone worth a foray into the hotel. Double rooms cost from €480 (£330).

More modest rooms with prices to match are available in the historic houses that are classified as residenze d'epoca. Simple en-suite rooms, with no restaurants on site but in central locations, are a cheaper option. Il Casato, via Casato di Sopra 33 (00 39 05 77 23 60 01; www.hotelrooms.it) and Il Casato Due, via Dupre (00 39 05 77 22 69 93; www.hotel rooms.it) charge from €150 (£103) for a double room.

Best restaurant

Local people mostly avoid the many eateries lining the Campo, but if a meal with a view of the great Palazzo Pubblico is irresistible, head for Al Mangia (00 39 05 77 28 11 21), Il Campo (00 39 05 77 28 07 25) or trendy new Liberamente with its transparent chairs (00 39 05 77 27 47 33). Indoors and out, Nello La Taverna (00 39 05 77 28 90 43) in via del Porrione serves vegetarian delicacies such as chick pea and artichoke pie with tomato coulis, and parcels of grated pasta, beans and cheese. Three courses with wine cost around €35 (£24).

Best sightseeing

The star turn at the Palazzo Pubblico is the frescoed depiction by Simone Martini of the effects of Good Government and Bad Government. At the Duomo, the winning horse in the Palio (2 July and 16 August) clip-clops up the steps for a blessing. The (nowadays, hard) hats of the riders hang in thanksgiving in a side chapel. The humbug-striped cathedral is a riot of pattern and shamelessly ill-matched treasures. The nearby Pinacoteca houses the city's exceptional collection of painting from the 15th-century onwards. At the Museo delle Opera del Duomo, the Duccio Maestà is the star attraction. Visitors are encouraged to leave the Campo and go "urban trekking" up and down the three hills on which the city is built, for vistas that include beautiful Chiantishire.

Best cultural attraction

An orphanage and hospital opposite the Duomo has cared for the sick and poor since the 15th century. The story of this ministry, complete with accurate depictions of early medical methods, is recorded in an entirely frescoed room in the Hospital of Santa Maria della Scala, a labyrinthine building that was still a working hospital until recently. Painstaking restoration has revealed arresting frescoes by Domenico di Bartolo and contemporaries. Tableaux include the dream of the mother of the hospital's founder, Sevore, in which she sees abandoned babies climbing a rope ladder to the Virgin. A seven-day pass to the Palazzo Pubblico, Santa Maria della Scala, the Baptistry and other star turns is a bargain at €16 (£11).

Best shopping

Nannini, Banchi di Sopra 24, has the best panforte, Siena's fruit and nut cake, and cantucci and ricciarelli, tough, nutty biscuits for dunking. Fine art souvenirs such as calendars and stationery cost a fraction of comparable products at home. The Fortress has a reputable enoteca: look for good deals on red Brunello. The Wednesday-morning market at La Lizza attracts shoppers from miles around. The antiques market at Piazza del Mercato is on the third Sunday of the month.

Best nightspot

Owls like to congregate in the cafés of the Piazza del Mercato, the via Pantaneto and the Piazza del Sale. The Café del Corso opposite Nannini will still serve a slug of coffee at 3am. In the summer, classical concerts attract world-class artists. The music school is in the Palazzo Chigi Saracini, open to visitors, for the first time in 200 years, until 15 June.

How to get there

Ryanair flies from Stansted to Rome Ciampino from an advertised £1.99; trains and buses from Rome to Siena take around two hours and cost from £15 return.

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