39 Best Sights in Umbria and the Marches, Italy

This scaled-down copy of the Palazzo Ducale in Urbino (Gubbio was once the possession of that city's ruling family, the Montefeltro) contains a small museum and a courtyard. Some of the public rooms offer magnificent views.

The heart of the town is the majestic Piazza del Popolo, dominated by the Gothic church of San Francesco and the Palazzo del Popolo, a 13th-century town hall that contains a graceful Renaissance courtyard. The square functions as the living room of the entire city and at dusk each evening is packed with people strolling and exchanging news and gossip—the sweetly antiquated ritual called a passeggiata—performed all over the country.

Built above the Roman Forum, Piazza del Popolo is Todi's high point, a model of spatial harmony with stunning views of the surrounding countryside. In the best medieval tradition, the square was conceived to house both the temporal and the spiritual centers of power.

The 14th-century Palazzo dei Consoli houses Deruta's Municipal Picture Gallery, and is only open on Sunday. The rich collection displayed over two floors includes frescoes and paintings by the Renaissance artists Perugino and L'Alunno, among other works from local churches. Upstairs, the Pascoli Collection features 17th- and 18th-century canvases, donated by a descendant of the prominent art collector and writer Lione Pascoli. Artists represented include Giovanni Battista Gaulli, Sebastiano Conca, and Francesco Trevisani.

If you're short on time but want a quick look at the cisterns and caves beneath the city, head for the Pozzo della Cava, an Etruscan well for spring water. On a walk through nine excavated caves you can see the fascinating ruins of medieval houses and unearthed archaeological artifacts.

A labyrinth of little streets, alleys, and arches, this underground city was originally part of a fortress built at the behest of Pope Paul III between 1540 and 1543 to confirm papal dominion over the city. Parts of it were destroyed after the end of papal rule, but much still remains. Begin your visit by taking the escalators that descend through the subterranean ruins from Piazza Italia down to Via Masi. In summer, this is the coolest place in the city.

The two great Umbrian artists hold sway in this 16th-century basilica. Pinturicchio's vivid frescoes in the Cappella Baglioni (1501) are striking for their rich colors, finely dressed figures, and complex symbolism. Among his finest works are the Nativity, Christ Among the Doctors and the Annunciation (look for Pinturicchio's self-portrait in the Virgin's room). Two pillars on either side of the apse are decorated with frescoes by Perugino (circa 1450–1523).

Dating from the time of the Emperor Augustus (27 BC–AD 14), this structure was originally dedicated to the Roman goddess of wisdom, and in later times it was used as a monastery and prison before being converted into a church in the 16th century. The expectations raised by the perfect classical facade are not met by the interior, which was subjected to a thorough Baroque transformation in the 17th century.

The Romans who colonized the city in 241 BC constructed this small theater in the 1st century AD; for centuries afterward it was used as a quarry for building materials. The most intact portion is the hallway that passes under the cavea (stands). The rest was heavily restored in the early 1950s and serves as a venue for Spoleto's Festival dei Due Mondi. The theater was the site of a gruesome episode in Spoleto's history: during the medieval struggle between Guelph (papal) and Ghibelline (imperial) forces, Spoleto took the side of the Holy Roman Emperor. Afterward, 400 Guelph supporters were massacred in the theater, their bodies burned in an enormous pyre. In the end, the Guelphs were triumphant, and Spoleto was incorporated into the states of the Church in 1354.