Almost unanimously considered nowadays as one of the greatest Latin American writers of the contemporary era, the Chilean Roberto Bolaño put into question, in his well-known novel (1998), the structure and meanings of journey. Seen not only as the characters’ capacity to move from one place to another, each journey described within this book acquires symbolic meanings, being in turn an intricate process of initiation or a personal quest of the protagonists. Nevertheless, journey, as seen in Bolaño’s fiction, also implies sometimes the idea of exile, a very specific exile within literature, the Chilean writer’s characters representing contemporary expressions of the great Homeric heroes or absolutely original embodiments of Joyce’s Ulysses himself.