Scholars studying international retirement migration (IRM) refer to lifestyle migration to explain the motives and aspirations of older individuals who choose to relocate out of their home country. Here I investigate French retirees’ reasons for migrating to Southeast Asia, and their sense of purpose in doing so. Interviews with 17 retirees living in Sihanoukville, Cambodia, and Vientiane, Laos, whose narratives evoked some degree of historical relevance, suggest that certain migration choices are best understood in the context of a postcolonial moment comprising colonialism and its dissolution, the Cold War, and the postcolonial diaspora. Such an approach illuminates the relationship between history, migration, and pensioners’ respective biographies in explaining their retirement journeys to former colonies, and in how these experiences foster multifaceted hybrid identities embedded in various historical moments.