Ancona, the regionâ€™s capital and â€œeastern gatewayâ€. Urbino and its Rennaissance is a World Heritage Site. The one hundred towers of Ascoli Piceno. The Middle Ages of Fermo and the Sanctuary in Loreto. The 14th century walls of Jesi and Macerata with its Sferisterio (sphaeristerium). Ancient Roman Pisaurum, Pesaro, and the Flaminian Way in Fano.