Jineterismo, frequently used as a synonym of prostitution, became a widely used term in Cuba in the 1990s. Perceived by some as a social problem that needed to be eliminated, and as a liberating economic strategy by others, the term is discussed in major studies on contemporary Cuba and often mentioned by travel writers outside of Cuba. Some scholars define jineterismo as the new female strategy adopted by young women to obtain hard currency, on the other hand, an influential Cuban politician, criticised jineteras, stating that they were immoral and embarrassing to Cuba. This study seeks to understand the meanings and practices of jineterismo from a bottom up perspective. Using ethnography to locate answers about jineterismo, I explore the meanings of the concept based on the views of those that Cuban society labels as jineteras. The central argument put forward in this study is that jineterismo has to be analysed as a diverse set of practices caused by a diverse set of factors, and that it involves a heterogeneous group of individuals. Jineterismo, I argue, ranges from the struggle to obtain hard currency to the practices involved in developing and maintaining romantic relationships with tourists, and is strongly informed by the desire to emigrate abroad. While jineterismo currently appears to be embedded in discourses of prostitution, this thesis highlights the romantic side of jineterismo and brings to the fore young Cuban women’s perceptions of Cuban men and life in Cuba, views that contrast significantly with their positive images of Europeans and the Western world. More importantly, the thesis improves our knowledge of jineterismo by offering a new perspective into the reasons that lead young Cuban women to seek relationships outside Cuba.