3 Best Sights in Montepulciano, Tuscany

Designed by Antonio da Sangallo il Vecchio, and considered his masterpiece, this church sits on the hillside below the town walls and is a model of High Renaissance architectural perfection. Inside is a painting of the Madonna that, according to legend, was the only thing remaining in an abandoned church that two young girls entered on April 23, 1518. The girls saw the eyes of the Madonna moving, and that same afternoon so did a farmer and a cow, who knelt down in front of the painting. In 1963, the image was proclaimed the Madonna del Buon Viaggio (Madonna of the Good Journey), the protector of tourists in Italy.

The unfinished facade of Montepulciano's cathedral doesn't measure up to the beauty of its neighboring palaces. On the inside, however, its Renaissance roots shine through. The high altar has a splendid triptych painted in 1401 by Taddeo di Bartolo (circa 1362–1422), and you can see fragments of the tomb of Bartolomeo Aragazzi, secretary to Pope Martin V, that was sculpted by Michelozzo between 1427 and 1436.

Filled with handsome buildings, this large square on the heights of the old historic town is Montepulciano's pièce de résistance.