Urbino
A UNESCO World Heritage site and one of the great Renaissance cities, Raphael’s birthplace, and home to the Palazzo Ducale, which holds Piero della Francesca’s Flagellation and Madonna of Senigallia, and Raphael’s La Muta. Worth the drive (about 1h45 each way). You can stop at the borgo of Gradara on the way back. The castle is well preserved and only a few minutes off the A14.