This paper presents findings of a pilot qualitative study of Caribbean students undertaking overseas immersion primarily for the purpose of perfecting their knowledge of a language and understanding of a culture other than their own. The participants were a group of eleven University of the West Indies (UWI), Cave Hill (Barbados) graduates, five in Colombia, six in France, all working as English-language assistants for eight to ten months during the 2007-2008 academic year. Three data collection instruments were used: (1) diaries kept by participants throughout the sojourn; (2) eleven semi-structured interviews averaging 56 minutes duration, with eight of these being after the sojourn and three during (after three months); and (3) a questionnaire administered six months after return. One of the principal functions of this study is to fill a gap in the research by assessing how the relative size and "recognizability" of the home and host states may affect the sojourner's experience. The results of this study are discussed. (Contains 1 note.)