One day
Spend the morning in the Palazzo Ducale and the Galleria Nazionale delle Marche — the courtyards, the duke's studiolo, and the great paintings, Piero's Flagellation and the Ideal City among them. Have a crescia-and-casciotta lunch, then climb the brick lanes to Raphael's birthplace and the frescoed Oratorio di San Giovanni. In the late afternoon, walk up to the Fortezza Albornoz for the twin-tower view at sunset, and dine in an old-town osteria.