This paper investigates the impact of the global 2008 crisis on the Caribbean region, with particular focus on its many small tourism-dependent economies. Specialization in tourism and, in some cases, offshore financial services has been a successful specialization strategy for many small economies but has made them highly susceptible to exogenous economic shocks. The paper utilizes cluster analysis to identify five distinct pre-crisis patterns of sectoral specialization in Caribbean economies generally. The 2008 crisis is shown to have had very distinct cluster-specific effects, with small economies specializing in tourism and financial services being the worst affected. These findings raise important questions regarding the future sustainability of this sectoral growth template, previously adopted by many successful small economies.