The appearance of Tunisian communities in Sicily towards the mid-1960s was one the very first cases of international migration towards twentieth-century Italy. However, the coexistence of immigration with the difficult economic situation of the destination area still raises interpretational difficulties: how is it possible that one of the poorest European regions became an area of immigration and, the very first in its own country? This article suggests an answer to this question adopting a comprehensive approach integrating political, social, and economic elements. The article defines and frames migrants movements in the Channel of Sicily as components of a broader migration system connecting Sicily and Tunisia. The deconstruction of the migration system follows three directions: the Italian institutional and diplomatic background against which Tunisian migrations emerged, the economic salience of transnational economic activities in the Channel of Sicily, and the history of connections between the opposing shores of the Central Mediterranean.