Cuba finds itself at the centre of various discourses yet again, as publications such as "The Economist" and others debate the future of Cuban culture and society. While issues of economics, ideology and politics are fertile ground for discussion, they do not encompass the totality of such a conversation. The authors argue that critical to the conceptualisation of the Cuba of tomorrow is an awareness of Cuban youth cultures, the multiplicity and ideations of those cultures and the role that hip hop and reggaetón play in affording an alternative spaces for self-expression, critical dialogue, a fashioning of the what is to come and the receding futures of Cuba's tomorrow.