This thesis investigates the everyday material, ethical, and emotional quandaries of transnational living navigated by Cuban migrants in Spain. Moving beyond reductive accounts of economic migration for which Cuba is often taken as an exemplar writ large, I propose an expansive, inclusive, and feminist approach to the “economic” that reveals the myriad gendered demands, dilemmas, and desires generated by diasporic living. Drawing primarily on thirteen months of ethnographic fieldwork in Spain among Cuban migrants and their relations, I illuminate transnationalism as a way of being, seeing, and feeling in the world that comes to inform people’s expectations about what makes for a meaningful life and where it can be found, in addition to their perspectives on moral personhood, relationality, and belonging. Transnational ways of being, I demonstrate, are not limited to the diaspora, but also permeate social life in Cuba, affecting those who remain on the island. For Cuban migrants in Spain, I posit that becoming transnational entails cargando con Cuba – taking on, carrying, and reckoning with “Cuba” – a form of embodied labor that shapes and is shaped by their perceptions of self, orientations toward migration, desires to depart, stay, or return, and perspectives on how to engage ethically with the world around them. Grounding my analysis in my interlocutors’, I contend that cargando exemplifies the inherent relationality and materiality at the heart of migrant struggles. Ultimately, this thesis tenders an original ethnographic contribution to the study of gender and transnationalism, shedding novel light on the tensions and continuities that emerge through migration between the individual and collective, autonomy and dependence, desire and obligation, and self and other.