This article refers to just one example of specificity of context, the small island community. Islands can be viewed as well-bounded communities, often with an identity that seeks to be one step removed from being the politically dependent neighbour. Two islands serve to exemplify the significance of context: The Island of Jersey (Channel Islands), which exemplifies difference from Western societies that are so well addressed in current leadership literature; and the Kingdom of Tonga in the South Pacific, which shows characteristics of an island culture that has similarities with Jersey. Although the two island states are geographically many miles apart, there are specific similar challenges faced by principals that are related to the island context. Both islands have their own independent political structure, are self-governing, have their own language or dialect and design their education system to reflect their own social norms, values and ideals. In this article, the author explains that island territories are bounded communities--distinct and separate--but linked to other nations by historical, social and economic ties. The author asserts that Jersey and Tonga can be identified as particular community contexts. Thus, educational leadership is framed not just by the social and political system, the influence of other nations in terms of economic and policy-led initiatives, but also by the very specific way in which islanders interact and act to maintain their own "national difference."