By 2050, the world’s population of international migrants is estimated to top 400 million. A small but growing number of those migrants are leaving well-developed, affluent countries best known for receiving immigrants to settle in less well-developed countries better known for sending migrants. These migrants of relative privilege, many of them retirees, are motivated primarily by a desire to enhance their quality of life. Although this migratory flow receives much less attention than more familiar, and reverse, movements of laborers or refugees, its implications for the destination sites, sites of origin, and study of international migration generally are significant. This article will examine the contemporary border crossing of privileged migrants, the economic, political and cultural stakes for the countries and individuals involved, and the implications of incorporating privileged mobility into the study of global migration and transnationalism.