Lifestyle migration, the flow of relatively affluent people from developed to developing countries, is characterized by the search for ‘lifestyle’ destinations with warm climates, reduced costs of living, and perceived higher quality of life. Mexico, Costa Rica, and Panama are three current major lifestyle migration destinations in Latin America. In this article I explore the emergence of this relatively new phenomenon in the Bocas del Toro Archipelago in Northwestern Panama by discussing the contradiction between lifestyle migrants’ idealized perception of place and local realities. I also introduce the implications of these contradicting versions of reality, and how they play out at the local level. Results show that, in general, foreign residents are attracted to Bocas del Toro as a physical manifestation of globally produced images and perceptions of tropical island living. However, an in-depth exploration reveals contradictions between expectations and reality. I suggest that foreigners exhibit a set of attitudes and behaviors towards their new home that are defined by a shared cultural and economic background that, on the ground, contribute to the creation of emerging markets, land conflicts, and changes in environmental practices. The ensuing narrative is contingent upon tensions between and within social, political, and ecological variables at the global and local levels.