Siena invented a painting language of gold leaf, punched haloes and tender Madonnas that Florence later overwrote with perspective. Three days here follow that thread through cathedral pavements, hospital wards turned fresco cycles, and ward museums few visitors enter.
Duccio di Buoninsegna's Maestà (1308-11), once the cathedral's high altarpiece, now split across two facing walls — front panel and the 26 narrative back scenes. Open 10:00-19:00 summer; entry via OPA SI Pass. Includes the Facciatone climb.
56 inlaid marble panels by Beccafumi, Pinturicchio and others, uncovered roughly late June to July and mid-August to October. The Piccolomini Library holds Pinturicchio's ten-scene fresco cycle of 1502-08 in near-original colour.
The definitive Sienese School collection: Guido da Siena, Simone Martini, the Lorenzetti brothers, Sassetta, Sano di Pietro and Beccafumi, hung chronologically across two floors of a 15th-century Gothic palace on Via San Pietro.
Beneath the cathedral apse, a Gothic baptistery whose hexagonal font (1417-31) carries bronze relief panels by Jacopo della Quercia, Ghiberti and Donatello — Donatello's Feast of Herod is early Renaissance perspective in bronze.
A thousand-year-old pilgrim hospital turned museum complex. The Pellegrinaio ward keeps Domenico di Bartolo's 1440s secular fresco cycle of hospital life, and the lower levels hold the Oratorio di Santa Caterina della Notte and the Etruscan collection.
The curving Via di Città holds ceramic studios painting contrada crests, the Antica Drogheria Manganelli of 1879, and bookbinders selling marbled paper. Palazzo Chigi-Saracini's courtyard sits halfway along, open to walk into free of charge.
Count Guido Chigi Saracini's 1932 conservatory, where Casals and Segovia taught. The palace holds a private picture gallery and a frescoed concert hall; guided visits run on set afternoons and the summer Chigiana International Festival fills July and August.
Siena's oldest theatre, built into the civic palace with a Baroque horseshoe auditorium rebuilt by Bibiena in 1753 and restored after an 1742 fire. It still stages the autumn prose season and Chigiana concerts; the Teatro dei Rozzi nearby runs a parallel programme.
A vast brick preaching barn on the Camporegio ridge holding Andrea Vanni's contemporary portrait of Catherine of Siena and, in the Cappella di Santa Caterina, Sodoma's 1526 frescoes of her ecstasy. Open 07:00-18:30, no charge.
One of seventeen ward museums, each keeping its Palio banners, costumes and oratory. The Snail contrada's collection sits behind its own church in the Val di Montone; visits are by appointment through the contrada office, generally free with a donation.
Beside San Francesco, an upper oratory with a 16th-century cycle by Sodoma, Beccafumi and Girolamo del Pacchia on the life of the Virgin, plus the Museo Diocesano's gold-ground panels below. Seasonal opening, roughly March to October.
The vaulted brick casemates of Cosimo I's 1560s fortress house Italy's national wine collection, with tastings of Brunello and Chianti Classico under the ramparts. The bastion walk above gives the standard evening passeggiata for Sienese families.