The central role of ICT in development and its ethical implications have kept the longstanding discussions of the Digital Divide active in the international development and research communities, with new perspectives on how to measure and interpret this inequality. In this paper, we examine the nature of the Digital Divide in the Maldives - between the nation's capital and the Atolls, between the Atolls and across the nation, and the evolution of these divides over time. In order to inform more effective policy interventions, we also attempt at identifying clusters within the country that share similar Digital Divide concerns. The results show significant disparities in the penetration of digital technologies. While we can observe the narrowing of the Digital Divide over time, the divide remains significant between the capital and the rest of the nation. Finally, we discuss the implications of these results to ICT development of Small Island Developing States.