This thesis examines the complex experiences of Irish immigrants in city and province of Santiago de Cuba. For some pre-Famine Irish immigrants, Cuba was an island of opportunities, and these often lay in the burgeoning sugar and coffee industries, industries that were dependant of enslaved labour and the slave-trade. Santiago de Cuba, a small city of almost no relevance to the Spanish American empire, appears as an unlikely destination for Irish migrants, but, although they were only a handful of families, their contribution is significant and under-explored. The present work examines those Irish families who settled permanently in Santiago from the 17th century until the eve of the Irish Great Famine in 1845. They are composed of two distinctive groups of Irish immigrants. The first one arrived from Spain throughout the 17th and 18th centuries. They developed a sense of symbolic Irish identity, expressed through naming practices, and had a hand in creating the élite cohort into which the immigrants of the second group inserted themselves in the early decades of the 19th century. The first group employed strategies to achieve social mobility and to maintain some degree of ethnic cohesion. They saw in marital alliances as a highly strategic practice that placed them into the local élite and into key colonial institutions in order to assimilate and integrate into their host society. By contrast, the second group was composed of a wider cohort of clearly transnational and trans-imperial adventurers. They sojourned in the United States, towards which market they focused their enterprises by creating trading firms and investing in coffee cultivation. They exploited the interstices of the Spanish and British empires, and of the United States’ “informal one”, to become some of the wealthiest planters and merchants in eastern Cuba. By 1827 these groups had merged into one élite that was politically and socially conservative, and religiously Catholic. They were fiercely pro-slavery and fervent supporters of the maintenance of the Spanish colonial status quo. The arguments made in this work are sustained in primary sources such as letters, genealogical data, parish records, business letters, and diplomat’s dispatches, among others. These sources were found in archival collections in Cuba, Ireland, the United Kingdom, the United States, and Spain.