Memories of maritime glory echo through the winding streets of charming Ancona, where handsome palazzos and elegant churches bear witness. Established by the Greeks on Italy’s outer elbow, the ancient harbour anchors undulating hillsides and rugged Adriatic coastline peppered with fishermen’s caves and pearlescent beaches. Cast your eyes towards the rising sun through the Arch of Trajan, Roman gateway to the east, and watch life unfold at ageless waterfront trattorias and cobbled piazzas. Lion-flanked San Ciriaco Cathedral stands sentinel on a hill above the port, rewarding those who make the journey with oil painting scenes as sunset bathes all in an amber glow. Further north, the UNESCO historic centre of Urbino beckons with its Renaissance walls that survive virtually intact.