A palimpsest of multiple Mediterranean cultures, Sicily is a crossroads of civilizations and a provincial backwater, traditional and yet, from time to time and in particular milieus, modernist. This essay undertakes a journey into Sicilian cultural spaces, places, and traditions beginning with the enlightened travelers of the Grand Tour and ending with postmodernist wanderings along the shores of the Mediterranean Sea. My approach weaves film and literature together in order to map the multifaceted Sicilian identities. The island becomes an image for a magnificent past and for a present of missed opportunities, both individual and collective. Among the works and artists discussed, Goethe’s Italian Journey, Michelangelo Antonioni’s L’avventura, Nanni Moretti’s Caro Diario, Giuseppe Tornatore’s Nuovo Cinema Paradiso, Roberto Andò’s ,em>Il manoscritto del Principe, and Giuseppe Tomasi di Lampedusa’s Il Gattopardo.