How have Malta and Cyprus – both EU members – transitioned from colonial island states to independent democracies? With the assistance of primary documentation this book traces the difficult path of these two states to becoming independent liberal democracies by using the pathway of democratization through decolonization. Using socio-economic and political data, analysed through the microscope of political science and international relations theories, Isabelle Calleja Ragonesi charts the progress of the two islands in the context of a number of four distinct phases. Firstly decolonization, independence and achieving the status of procedural democracies; secondly post-colonial independence consolidating democracy and regime breakdown; thirdly sovereign nation-state status and second attempts at consolidating democracy and finally attempting to reach substantive democracy status and EU membership. The study of these two states is contextualized within the context of democratization in Southern Europe and the cases of Malta and Cyprus provide new insights on the region for scholars of political science and international institutions.