The comparative reading of postcolonial spaces of port cities on both sides of the trading poles offer a new understanding of their cultures and urban structures and reveal overlooked relations on a global level. The harbors have been key sites in the transfer of goods, people and cultures, the connection of distant but related worlds as well as the execution of power. These spaces hence need to be read relationally. They are formed by and represent uneven power relations of the colonial past and the corresponding agency of this construct up to the present day. As such, a correlated study of port cities may reveal a deeper understanding of them. Flensburg and Charlotte Amalie are the two poles of a post-colonial relation that is not yet analyzed systematically. They are connected by a shared history that still powerfully shapes their cultural and physical spaces. The significance of their past as two extremes in the Danish colonial empire is analyzed through the lens of cultural theories from the Caribbean and post-colonial urban theories. As a case study, this research frames a novel view of the past and present relation between Europe and the Caribbean, with a particular focus on the ports as spaces of interaction and potential hybridization.