This article follows a research project that collects oral histories of bilingual education teachers from Puerto Rico who migrated to the US Virgin Islands in the late twentieth century. The teachers' oral histories are used as a case study that provides in-depth analysis of competing discourses related to education and globalization in these two US Caribbean territories. The paper begins by examining intersections between migration and globalization in the Caribbean. Analysis of oral teachers' accounts of events experienced in both islands is provided, with a focus on how they dealt with tensions tied to floating migration, constructions of "otherness," language use, and racial formations in their articulation of transnational identities and cultural differences. (Contains 2 notes.)