Small island states, due to their size, remoteness and dependence on foreign capital, are often susceptible to various global disruptions and crises. The effects of such crises can be chaotic, seriously damaging their economies and altering their systems. However, in the context of tourism crisis management, linear approaches are predominant overlooking the chaotic characteristics and transformations of the complex tourism system. In response, this research investigates the implications of the economic crisis and the interaction effects of unforeseen events, on Cypriot tourism through a chaos theory perspective. Based on semi-structured interviews, archival document analysis and a pertinent literature review, findings indicate that the evolution of Cyprus tourism was not a linear process, but instead iterative, characterised by interactions of several endogenous and exogenous events that have shaped its systemic transformation. The research reveals the lack of comprehensive policy responses to crises that would enable the sustainable tourism development of Cyprus. The paper concludes that it is imperative for small island states to understand holistically the interrelated dimensions of crises and therefore mitigate their detrimental consequences. To this end, tourism policy needs to realise that crises and sustainability are not linear processes but evolving systemic configurations that necessitate the preparedness of tourism policy-makers and stakeholders to anticipate change and swiftly respond.