Montepulciano’s bare-brick, homely cathedral was completed in 1680 on the site of a much earlier church pulled down (the relatively new 15th-c. bell tower was left in place) to make way for what was to have been a landmark worthy of the noble neighbors on Piazza Grande. The city was by then out of funds, however, and the exterior was never sheathed in marble as planned. Inside is Montepulciano’s great work of art, a 1401 gold-hued altarpiece by Taddeo di Bartolo (1363–1422) of the “Assumption of the Virgin with Saints.” Bartolo was one of the Sienese artists of the generation after the 1348 Black Death, and this is one of his greatest works; he must have been pleased with it, as he included his self-portrait among the apostles gathered around the tomb of Mary. You can’t get too close to the massive triptych soaring above the high altar, which is a shame, because the charm lies in the detail of the many various panels. The main sections show the death of the Virgin, with the apostles miraculously summoned to her bedside; her assumption into Heaven, with most of the apostles also present, here surveying her empty tomb in amazement; and the Virgin’s coronation, an extremely popular theme among 14th- and 15th-century Italian artists in which Christ crowns his mother as queen of Heaven. Surrounding these scenes are various adoring saints and, along the bottom, episodes from the life of Christ. One particularly charming vignette shows a child shinning up a tree to get a better view of Christ entering Jerusalem.

The cathedral’s other masterpiece is a scattershot affair, the remnants of a marble sculptural group that the Florentine architect and sculptor Michelozzo (1396–1472) crafted between 1427 and 1436 for the tomb of papal secretary Bartolomeo Aragazzi, a humanist and prominent Poliziani. You’ve seen Michelozzo’s light touch throughout Tuscany: He designed the outdoor pulpit for the showing of the Sacra Cintola (girdle of the Virgin) in Prato ; redesigned the Palazzo Vecchio and designed the Palazzo Medici in Florence; and sculpted the statue of St. John over the door of Florence’s Duomo. You’ll have to walk around the church to see the bits and pieces of his work here in Montepulciano, as the tomb was disassembled in the 17th century when the original church on this spot was demolished; some pieces were stolen and have eventually found their way to the Victoria and Albert Museum in London, while others are rather randomly distributed around the cathedral. A reclining, hooded statue of the deceased is to the right of the central entrance door, and figures of fortitude and justice stand on either side of the high altar; leaning against a nearby pillar is the figure of St. Bartholomew, after whom Aragazzi was named.