This volume, which is divided into three parts, brings together critical essays and creative texts shedding light on how Italy is constructed as an “imaginary homeland” in Italian-Canadian literature and media. The critical essays included in Part I highlight how memory, (anti)nostalgia and (non)belonging are at the core of the representation of Italy in anglophone and francophone literary texts and TV programmes by Canadian artists with Italian origins. Some of these essays focus on how the transnational nature of these products is reflected at a linguistic level and how this is re-constructed through the translation into Italian. Part II focuses on Nino Ricci’s trilogy from a linguistic, media and translation perspective, investigating how Italy is filtered through the eyes of an Italian boy from a village in Molise to Canada. Finally, Part III works as a short anthology of different forms of creative writing by anglophone and italophone writers of novels, poems, plays, most of whom migrated from a number of areas of Italy to different parts of Canada. A Coda by a former director of the Italian Institute of Culture of Toronto and Montreal gives yet a further perspective on Italian-Canadians and Italy as an “imaginary homeland”.