This article analyses the role of border regimes and post-colonial ties in Caribbean migration between 1960 and 2010. Over this period, 18 out of 25 countries in the Caribbean region have experienced the closure of borders by their former colonial state, while the remaining seven former colonies have retained open borders with their metropolitan state. In view of the academic and policy debate about the effects of border restrictions, the Caribbean region allows the comparison of emigration volumes and migration destination selection from Caribbean countries with both closed and open borders. Moreover, because the Caribbean region was colonised by Britain, France, the Netherlands and the United States, we examine whether post-colonial ties influence long-term Caribbean emigration, allowing migrants to overcome border regime restrictions. The article finds that countries with closed borders with the former colonial state do not experience a decrease but rather a strong increase in long-term emigration. In fact, emigration gradually regains strength after border closure as migration channels to new destinations develop. Thus, border closure seems to encourage a weakening of ‘post-colonial’ migration patterns through the diversification of emigration towards destinations other than the former colonial state and its former colonies. Conversely, the increase of emigration from countries with open borders has decelerated and generally remained concentrated towards countries within the free-movement colonial sphere. This suggests that the post-colonial migration patterns may be associated with continuous open borders as much as with cultural and linguistic connections.