It is well-known that small states, because of their size, tend to be less endowed with natural resources than big ones. This makes small states vulnerable and raises the question if specific policies can be implemented to offset the drawbacks of their small size and to increase resilience. We address this question in this paper, thereby focusing on the role of connectivity – between states, organisations, parties, or otherwise – in understanding a country’s vulnerability and resilience. Here ‘policies’ are interpreted as ‘institutions’ in the sense of Douglass C. North (1990), i.e. as ‘humanly devised constraints that structure political, economic and social interaction’. We focus on the Caribbean area, which is characterised by a wide variety of small states, each with its own set of rules and regulations. Within this area, we concentrate on the relationship between three Dutch Caribbean islands, i.e., Aruba, Curaçao, and Sint Maarten, on the one hand, and the Netherlands, the former colonizer, on the other hand. As a first step we have measured the economic vulnerability and resilience of 17 Caribbean island states, both dependent and independent, employing the theoretical framework proposed by Lino Briguglio. The outcomes show that the three Dutch island states are performing comparatively well, although there are individual differences. We provide a first effort to explain this outcome in terms of the continuing interest of the three island states to keep their ties to the former colonizer viable. Here the presence of ‘systemic interest’ as shown by the stakeholders appears to be a most important variable.