The measures introduced by Raúl Castro since 2008 and the most recent US–Cuba policy change indicate that Cuba is shifting from a planned and highly centralised state socialist economic model toward one in which economic actors and markets become main drivers of the economy. The examples of Asian and Central and Eastern European socialist countries suggest four distinguished pathways for such transition. The question is which one may provide a feasible model for Cuba. Based on the country's economic and population structure, this study places the Cuban case within the framework of socialist economic transitions and explores some policy implications.