The little town of Urbino is a UNESCO World Heritage Site that was once a great center of learning. The University has about twenty thousand students, considerably more than Urbino's resident population of approximately fifteen thousand. You'll also find the Galleria Nazionale delle Marche (National Gallery of The Marche) with Titian's Resurrection and Last Supper. The city also contains several Renaissance churches worth visiting.
Ancona is a port city that was largely destroyed during World War II. Among its sights are the Twelfth Century Duomo di San Ciriaco (Saint Ciriaco Cathedral) and the Romanesque Santa Maria della Piazza.
Ascoli Piceno is a valley town of about fifty thousand people. You'll want to see the Piazza del Populo (Square of the People) and the Thirteenth Century Palazzo dei Capitani del Populo (Palace of the People's Captains) and several other historic churches. Try to get to Ascoli Piceno for the first Sunday in August to enjoy Renaissance costume parade and jousting tournament.
The Marche has many regional specialties, for example brodetto (fish soup) with thirteen kinds of fish and seafood. See our companion article I Love Touring Italy - The Marche Region for a sample menu and more information on Marche wines as well as an in-depth examination of its tourist attractions. The region is home to two DOCG (the G stands for Guarantita) red wines, the Montepulciano-Sangiovese based Rosso Conero Riserva and the Vernaccia di Serrapetrona based on a local grape.