In 1974, the Republic of Cyprus and the Republic of Trinidad and Tobago, both former British colonies, experienced significant events that permanently altered their economic and social realities. The coincidence of these occurrences offers an opportunity for a historical comparison of island development. In effect, this paper argues that the economic paths of these islands were shaped largely by their responses to neo-liberalism. Cyprus’ support for domestic enterprises and resistance to neo-liberal policies throughout the early 1990s compared to Trinidad and Tobago’s forced acquiescence to them and reliance on its energy sector explain the difference in their economic trajectories. Analytically, I argue that island nations can chart a course for economic strategies that benefit more of the population despite neo-liberal pressure to adopt policies that advantage global capital. This comparison supports the island studies position that islands have distinct place-based and/or historical capacities for resourceful and creative tactics towards economic autonomy and development