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Siena’s medieval town hall is a genteel brick palace. The rooms were so gorgeously decorated with early 14th-century art – including Simone Martini’s Maestà and Ambrogio Lorenzetti’s incomparable Allegory of Good and Bad Government – that they’ve been turned into a museum (see Siena’s Museo Civico).

Siena’s half-moon of a public square is one of the loveliest piazze in all of Italy, its broad slope home to the biannual Palio horse race and an ever-changing cast of strollers, coffee-drinkers, readers and picnickers. So rich is it in sightseeing opportunities that it counts among Tuscany’s Top 10 (see Siena’s Campo & Palazzo Pubblico).

This massive Gothic cathedral complex is filled with art by such masters as Michelangelo, Pisano, Pinturicchio, Bernini, Duccio and Donatello. It qualifies as one of Tuscany’s Top 10 sights, and is fully covered on pages 26–7.

The Pinacoteca boasts a comprehensive collection of Sienese painting (though the masterpieces of the school are housed elsewhere). Among the earlier gems, seek out various 14th-century Madonnas by Simone Martini and Pietro Lorenzetti. Compare Beccafumi’s cartoons (full-sized preparatory sketches on cartone , or “large paper”) for the Duomo’s floor panels and his Mannerist Christ Descending into Limbo to rival Sodoma’s High Renaissance works.

This massive, architecturally uninspired brick church of 1226 contains a portrait of St Catherine by her contemporary and friend Andrea Vanni. The saint’s mummified head and thumb are revered in a chapel decorated with frescoes on her life by Sodoma (1526) and Francesco Vanni. Matteo di Giovanni executed the saintly transept altarpieces.

The best sections of this former hospital, which ran from the 9th century to the 1990s, are mentioned on page 28. The Renaissance frescoes in the Sala del Pellegrino depict scenes of hospital life not too different from today – a monkish surgeon doctoring an injured leg, another taking a urine sample, a third nodding off as his patient describes symptoms. Several spaces in the building host changing exhibitions.

The vaulted cellars of the massive 16th-century Medici fortress are filled with Italy’s national wine museum (though, since vintners send in cases only on a voluntary basis, it’s far from comprehensive). Everything is for sale, and a selection of bottles is opened daily so that you can sample Italy’s oenological bounty by the glass at small tables or outside on the terrace.

Siena’s main passeggiata street (for evening promenading) is lined with palaces. Until Palazzo Pubblico was finished, the city council met in the piazza wedged between San Cristofano church and the 13th-century Palazzo Tolomei, now a bank. Further up the street, Piazza Salimbeni is flanked by Renaissance Palazzo Tantucci, Gothic Palazzo Salimbeni and Renaissance Palazzo Spannocchi. Together this group of buildings houses Monte dei Paschi di Siena, the city’s chief employer and oldest bank (established 1472), and its small, worthy collection of Sienese paintings.

The house in which the saint was born was made a sanctuary in 1466, with a modest Baroque church containing the 12th-century Pisan Crucifixion that gave Catherine the stigmata, a brick loggia (constructed in 1533 by Baldassare Peruzzi) and a small oratory with Baroque paintings by Il Riccio, Francesco Vanni and Il Pomarancio. Follow the staircase down past Catherine’s cell to see if the Oratorio dell’Oca and its frescoes of angels are open.

This Romanesque church contains some fine altarpieces covering all eras of Sienese painting. Highlights are Coppo di Marcovaldo’s Byzantine masterpiece Madonna del Bordone (1261), Matteo di Giovanni’s rather creepy Massacre of the Innocents (1491) and Francesco Vanni’s Mannerist Annunciation . In the transepts, the second chapels out on either side contain Gothic frescoes by Francesco and Niccolò di Segna and Pietro Lorenzetti, including another Massacre of the Innocents .