5 Best Sights in Tuscany, Italy

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.

Montepulciano's town hall dates from the late 13th century, though it was restructured in the 14th century and again in the mid-15th century. Michelozzo oversaw this last phase, using the Palazzo Vecchio in Florence as his inspiration. From the tower, a commanding view of Siena, Mt. Amiata (the highest point in Tuscany) and Lake Trasimeno (the largest lake on the Italian peninsula) can be enjoyed on a clear day.

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

Michelozzo had a hand in creating the beautiful travertine facade on the church of Sant'Agostino, which was built in 1285 and renovated in the early 1400s. He also sculpted the terra-cotta relief of the Madonna and Child above the entrance.