AbstractThe Dutch Windward Islands are examined to see if they throw any light on the problems experienced when very small island communities try to come together to form a larger political unit. The Constitution of 1954, though federal in intent, was unitary in practice, with the main island, Curacao treating the others like municipalities. However the island authorities are capable of asserting themselves against the centre. They control implementation, raise revenue and receive local political support. Because of the small size of the populations and civil services involved, island and federal officials collaborate harmoniously. Leading individuals are important for development, notably St Maarten's Claude Wathey. New initiatives also require effective negotiations to deal with off‐shore tourist organizations. However, there is little significant industry beyond tourism. In 1988 the three Dutch Windward Islands agreed to co‐operate with each other. Decentralization within the largest island could help this cooperation as could a regional association along the lines of the South Pacific Fo