Tuscany’s second-largest city is quite a sprawl, but tucked away behind what remains of medieval walls is an elegant old town, with airy piazzas and lovely churches. These fortifications didn’t do much to prevent the city from being sacked by papal forces in 1512, when thousands of citizens were slaughtered in the streets and the city came under the rule of the Florentine Medici family. A couple of centuries before then, Holy Roman Emperor Frederick II established a beachhead of his powerful and far-reaching dynasty in Prato, erecting the still-formidable though never-finished Castello dell’Imperatore on Piazza Santa Maria della Carceri. On the same square is a Renaissance attempt to restore classical ideals of order and symmetry, the templelike church of Santa Maria delle Carceri, designed on the plan of a Greek cross by Giuliano da Sangallo, a military engineer who branched out into churches and palaces under the patronage of the Medicis.

Prato’s textile trade has flourished here since the Middle Ages, and Palazzo Datini was the home of Prato’s kingpin of the medieval rag trade, Francesco di Marco Datini (1330–1410); you can still make out some of the frescoes on the proud facade at the corner of Via Mazzei and Via Rinaldesca (free admission). The scrupulously tightfisted magnate, who invented the promissory note, inscribed each of the 500 ledgers he left behind in wooden crates with his motto, "For God and Profit." He did his meticulous recordkeeping in rooms frescoed with charmingly soothing scenes of plants and animals. The Anglo-American biographer Iris Origia, who was raised in the Villa Medici in Fiesole and spent most of her life on a vast estate in Tuscany’s Vad d’Orcia , provides a fascinating account of Datini’s 14th-century world in her wonderful book “The Merchant of Prato.”

Doubting Thomas

As legend has it, the apostle Thomas was preaching in India when he was drawn up in a cloud of dust into the sky, where he witnessed the Virgin Mary rise from her tomb and ascend toward heaven. As she passed, she removed her belt and threw it to Thomas, saying, “Receive this, my friend.” (The gesture suggests the sacred equivalent of a femme fatale throwing a garment to a paramour as a keepsake to remember her by.) The recipient was the infamously Doubting Thomas, the apostle who was not present at the resurrection of Christ and, in one of Christianity’s most famous piques of skepticism, complained that until “I shall see in his hands the print of the nails, and put my finger into the print of the nails, and thrust my hand into his side, I will not believe.” In a scene that was a favorite with Renaissance masters, Christ reappears, instructing Thomas, “Reach hither thy finger, and behold my hands; and reach hither thy hand, and thrust it into my side: and be not faithless, but believing,” then added the admonishment, “blessed are they that have not seen, and yet have believed.” Taking pity on Thomas’ lack of faith, the Virgin threw him the girdle as proof positive that the she had ascended.

To Catch a Thief

Another Prato legend concerns the events of 1312, when an unfortunate fellow from nearby Pistoia named Giovanni di Ser Landetto, aka Musciattino, stole the city’s cherished relic, the girdle of the Virgin Mary. Rushing home in a thick fog, he became disoriented and wandered right back into the center of Prato, where he was apprehended, tied to a donkey’s tail, dragged through town, and burned at the stake. But not before his right hand was cut off—this the mob threw against the side of the cathedral, where its bloody imprint is said to be visible to this day.

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