The aim of this paper is to explore recent scenarios observed in migration and Spanish citizenship abroad, using Cuba as a case study. This project’s innovative contribution lies in its multimethod approach, which considers both normative and demographic factors while also including a qualitative and participatory dimension. Spanish migration to Cuba is a particularly interesting case, given the differences observed here as compared to other Latin American contexts, in terms of both the social policies involved and the Spanish migrants’ profiles and respective family strategies. We analyze migrant groups from the three regions of Spain that saw the greatest emigration to this Caribbean island: Asturias, the Canary Islands and Galicia. The results show the effects of Spanish social and migratory policies on migrants to Cuba and their families from the 1990s onward, in particular with respect to the law governing citizenship known as the “Grandchildren’s Act” (“Ley de Nietos,” 2007-2011). We discuss the different strategies and practices, both individual and collective, that arose from the new resources created by these policies. To conclude, we sketch out the repercussions of these new practices on intergenerational relationships, access to citizenship rights, and the reshaping of collective identities.