Known in ancient times as Corso del Ricco, Via Carolina is the main street of Castello and connects Piazza di Castello to Porticciola. Prestigious houses have been built along this street since the Middle Ages, with the large portals of merchants’ and artisans’ shops on the ground floor. The street’s current name pays homage to the English noblewoman, Caroline Shirley, who married Duke Lorenzo Sforza Cesarini of Santa Fiora in 1837.