Caribbean Small Island Developing States (SIDS), by their very nature, are vulnerable to external shocks. Research shows that the Caribbean subregion experienced 165 natural disasters between 1990 and 2008 and the total impact of natural disasters on the subregion was estimated at US$136 billion. The impact on the social sectors was estimated at US$57 billion, or 42% of the total effect. As small open economies, the Caribbean SIDS are also vulnerable to the vagaries of the international economic system and have experienced declines in tourism, merchandise exports receipts, remittances and capital flows throughout the financial crisis. The negative impact of natural hazards exacerbates the capacity of Caribbean SIDS to overcome the development challenges, such as those posed by the current global economic and financial crisis. Disaster risk reduction (DRR), therefore, is of critical concern to subregional governments and their people. For the purpose of this study, six Caribbean SIDS were selected for detailed analyses on the macro socio-economic impact of extreme events to the education sector. They are the Cayman Islands, Grenada, Guyana, Haiti, Jamaica, and Montserrat. This paper proposes that better integration of DRR in the education sector cannot be easily achieved if policymakers do not recognize the social nature of risk perception and acceptance in Caribbean SIDS, which necessitates that risk reduction be treated as a negotiated process which engages all stakeholders.