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The millennium ushered in unprecedented human mobility on a global scale, and in this Latin America and the Caribbean featured prominently as their nationals, many of them young, headed primarily to North America and Europe. Cuba was no exception and witnessed off-Island youth mobility to Canada and Western Europe of unprecedented levels. Whether planned or by happenstance, seeking economic and professional betterment or drawn by romance, love and a sense of adventure, the fact that they were young and educated and 'on the move' marked theirs as a generation apart from their parents and grandparents, for whom politics and migratory barriers had been paramount. The paper charts the imaginaries and realities, experiences and perceptions of young Cubans in the major cities of Toronto and Montreal in Canada and the European capital cities of Berlin, London, Madrid, and Paris, where most are to be found. Their ‘grounded cosmopolitanism' forms the backdrop to exploring comparatively how inter-generational differences are being played out, leading to a consideration of whether they are migrant settlers or rather sojourners on a trajectory, which may lead elsewhere or to a return to the Island.