Caribbean Small Island Developing States (SIDS) is one of the most vulnerable regions in the world to the impacts of climate change. The region has prioritized adaptation to climate change and has implemented many adaptation actions over the past 20 years. However, the region is becoming increasingly vulnerable to the impacts of tropical cyclones (TC). This paper analyses the impacts of TC on the region between 1980 to 2019. It aims to examine the economic loss and damage sustained by the region, identify the sectors most impacted, and ascertain the perspectives of key stakeholders on the factors that hinder building resilience. Statistical analysis techniques and semi-structured interviews were to unpack and understand the dataset. The paper finds that economic loss and damage has gradually increasing between 1980 to 2009 with a drastic increase between 2010 to 2019. The paper highlights the agriculture, housing, transport, and utility sectors as the most impacted. The findings also call to attention the need for increased access to adaptation financing for SIDS, the disadvantages of the income status that hinders building resilience, and the need for increased Early Warning Systems. The paper recommends revising the per capita national income as an eligibility criterion for accessing concessional development finance assistance, a comprehensive EWS for the countries in the region, and consideration of debt relief for countries affected by TC.