In this article, I take the case of North American lifestyle migrants living in Boquete, Panama to highlight (1) how the privilege of these migrants is remade following migration, (2) how it is experienced through intersubjective encounters within the destination, and (3) how it is variously interpreted by the migrants. Drawing on ethnographic research, the article demonstrates how subjective experience of privilege is framed and mediated by locally-inflected class relations and by racialised logics that the migrants carry with them into the destination. Through its focus on the contextualised constitution of privilege, and in particular the intersections of this with race and class, the article offers a unique contribution to a maturing field of enquiry on lifestyle migration.