The presentations in this session examine the lived experiences of the inhabitants of islands on both sides of the Atlantic from the sixteenth through the nineteenth centuries, to re-evaluate dominant narratives of the political, economic, and cultural power of European empires. By emphasizing local perspectives that were often overlooked or discounted by Spanish, English, and French authorities, these scholars reveal a complex web of island-wide, regional, and transatlantic connections and relationships, which contended with a range of imperial initiatives and the context of the slave regimes of the Atlantic world. Marc Eagle centers the Canaries in the late sixteenth and early seventeenth centuries, as an important intermediate stop on the voyages of outbound slaving vessels, prior to obtaining the majority of the African captives they would carry across the Atlantic. By sifting through notarial records reflecting the activities of crewmembers while in the Canaries, Eagle suggests a more contingent vision of these slaving voyages than the trade controls established by royal authorities in Spain recorded, and links the enslaved and free individuals on these ships with enduring commercial and social bonds between the Canaries and the Spanish Caribbean. On the opposite side of the Atlantic, Ernesto Mercado-Montero reconsiders the situation of the island of Saint Lucia in the Lesser Antilles from the late seventeenth to the mid-eighteenth century. In contrast to a traditional view of the island as a contested imperial territory overshadowed by robust plantation economies on neighboring islands, Mercado-Montero highlights the importance of the Indigenous Kalinago inhabitants in adapting to and limiting English and French imperial projects. In so doing, he positions Saint Lucia as a vital connection point in Atlantic commercial networks founded on the trade in enslaved Africans. Finally, Tessa Murphy moves the spotlight to the island of Trinidad, captured by the British in 1797, ten years before Great Britain outlawed the slave trade. In this intervening time, some 20,000 African captives were forcibly transported to the island, tripling the enslaved population. Murphy interrogates a range of sources to understand the encounter between established Creoles and recently arrived Africans and the process of constructing new social practices during and after this time, as slaveowners and administrators used their labor to re-orient Trinidad around sugar production. Together, these presentations offer a transnational reassessment of the limits of imperial control over the islands of the Atlantic, across the span of nearly three centuries.