This article explores significant notions of home and belonging among first- and second-generation Cuban immigrants in South Florida. The analyses are derived from biographical narrative interviews with six Cuban Americans. Three key subjects were in the biographical life stories—the notion of escape or leaving, the sense of home, and constructions of Cuban identity. In assessing these themes, we found there to be profound differences between the generations. Moreover, these Cuban biographies demonstrate how differing stories of migration provide new theoretical perspectives on immigration, transnationalism, and ethnicity. The experiences presented and discussed here connect to the ambivalence and complexity of belongingness and interpretations of Cuban-ness.