Climate change adaptation planning has rapidly expanded to assist with reducing vulnerability to current and projected impacts of climate change. In Caribbean small island developing states (SIDS), planned adaptation is viewed as essential to address their high vulnerability to climate change, and planning has begun in earnest across the region. However, there has been limited analysis of adaptation planning documents in the region to assess their quality and content. This study assesses adaptation planning documents from Caribbean SIDS, focusing on inclusion of key stages of adaptation planning that were identified from international and regionally specific adaptation guidance instruments. Eighty-nine Caribbean adaptation planning documents—including policies, strategies, programs, and projects—were assessed, revealing that they differ considerably from guidance instruments. Key areas for improvement include the need for (i) more direct linkages between identification of adaptation options and assessments of climate hazards, impacts, vulnerability, and risk; (ii) identification and appraisal of a range of adaptation options; and (iii) increased inclusion and usage of quantitative information about hazards and impacts. Addressing these deficiencies may help to improve the status of adaptation planning in the region and ultimately aid in reducing the high vulnerability of these island nations to the impacts of climate change.