This paper proposes to reflect on the complex relationships that Pirandello establishes in his texts with his own land; in particular, it analyses the literary space of Pirandello’s Sicily, observing it primarily from two points of view: in its topographical location and in its perceptibility through characters, myths and ideals. In order to bring out some specific aspects of the literary characterization of the island, the essay considers the ‘Sicilian path’ as a viable way to follow within the intricate labyrinth of the Novelle per un anno and examines thirty-two novellas, selected as most representative for this topic. Through a hermeneutical investigation, the present contribution aims to trace expressive modes and compositional strategies with which Pirandello describes complementary faces of the island: it focuses especially on the representation of Sicily as a multifaceted space, as a mythical land and as metaphor that imposes itself in the plurality of its facets. In its complexity, Sicily appears as a microcosm which shows a background of ancient chorality.