Cyprus and Malta are island states, among the smallest EU member states, both former colonies of Great Britain situated in the Mediterranean region, both non-NATO states and very open economies: they are often considered as identical twins. However, their divergent historical experiences, constitutions, economies and political systems make them two different states which need to be understood separately. As EU member states since 2004, they have shared some experiences but with different outcomes. After joining EMU in 2008, Cyprus faced major economic difficulties and had to be bailed out during the financial crisis while Malta sailed on almost unscathed. This chapter considers the salient differences and similarities in the two island states’ experiences by linking their history and domestic structures with their behaviour in world politics and the EU. The chapter also suggests the extent to which one can theorize about small state behaviour.