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In order to bolster military readiness and increase economic productivity in its long-neglected circum-Caribbean dominions, the Spanish Crown offered travel licenses, supplies, and land to Canary Islanders. These permissions, along with general poverty in the Canary Islands, led its inhabitants to emigrate in droves for many separate out-of-the-way coastal areas of Spanish America. They took up residence in Spanish American colonies such as Venezuela, Santo Domingo, Puerto Rico, Louisiana, and Florida. Like the Irish in North America, Canary Islanders became key parts of the social fabric in these colonies and also faced discrimination due to their ethnic origins. Peninsulares and creoles alike questioned their whiteness and called them “blancos de orilla.” Although some Canarian expeditions produced self-sufficient and autonomous peripheral settlements, others ended in desertion, desolation, and death. This paper focuses on the migration of families from the Canary Islands to the Spanish Caribbean and mainland settlements in Florida and Louisiana in the latter half of the eighteenth century. Records of their voyages speak to the complications, hardships, and mortality of this mobile, transatlantic population. Crown-sponsored repopulation of the circum-Caribbean also underscores the limits of militarization, social and economic reform, and socioracial perception in Bourbon Spanish America and the Atlantic World.