Osimo

Province: Ancona · Region: Marche · Population: 33,991 · Postal code: 60027

Osimo's people are "the headless ones": in the town hall atrium, twelve headless Roman statues gave the city the most self-mocking nickname in the Marche. Beneath the streets, a labyrinth of sandstone caves — with enigmatic symbols and reliefs — is toured by guide-light; above, the basilica keeps Saint Joseph of Cupertino, the flying saint and patron of students, who died here in 1663.

The Romanesque-Gothic cathedral on the highest point and the Roman walls complete a layered city, with the Conero countryside fifteen minutes away and the hill-country Verdicchio in the glass.