Cuba's economic restructuring in the past decade has involved the country's reinsertion into the global tourist market. One of the undesired consequences of the new tourism based economy has been the phenomenon of jineterismo, literally horseback riding, but used to indicate hustling or prostitution. Prostitution is associated with the pre-revolution era and is therefore a sensitive issue for the socialist government. At the same time, sex tourism has become an important source of hard currency income. This article proposes to see jineterismo as a complex social phenomenon that brings issues of race, class, gender and nation into play, ultimately challenging the revolutionary narrative of social and racial equality.