In chapter 2, the focus is on travel literature on Japan during the Fascist period, with specific attention to the shift in the mode of representing Japan before and after the Anti-Comintern Pact between Italy, Germany and Japan of November 6, 1937. This historical event is the watershed moment that serves to separate the chapter in two sections. Before the ratification of the anti-communist pact, a nationalistic approach informed by a sense of Italian cultural supremacy defined the attitude of Italians writers who landed in the East Asian country. The chapter’s second half traces Mussolini’s attempts to reshape the image of Japan in Italian public opinion. Beyond the propaganda, the chapter calls for a more nuanced assessment of this literary production. One example is offered by Pietro Silvio Rivetta, who seized the opportunity presented by the military alliance to reinforce his longstanding cultural project of introducing Japanese culture to Italy. Another example, is suggested by the case of Arundel Del Re, whose life spent across countries and continents exposed him to the pitfalls of his cosmopolitan identity, but also generated in him a sense of belonging, from East to West, that transcend the limits posed by national borders.