Vulnerability is an indispensable component of climate justice discussions, especially as it functions to identify the worst off in procedures and distribution framed in a Rawlsian interpretation of justice as fairness. Yet, vulnerability is a term replete in varying interpretations and analytical approaches; and choices in interpretation and approach are consequential to policy-making. Recent policy is constructed with disproportionate reference to biophysical conceptions of climate change, which, albeit useful, can lead to an overlook of the geographic and social context of vulnerability. In addition, when considering that this context is differentiated between and within scales, it is apparent that a multi-scalar framework provides a comprehensive approach to vulnerability studies. Small island developing states (SIDS) are often noted as being among the most vulnerable to climate change. This work assesses that claim through a multi-scalar examination of the political, geographic, and socio-economic conditions that engender vulnerability. What starts as a global scale case study of the political context of SIDS vulnerability is then focused upon a regional study of the socio-economic and geographic context of Caribbean, the most tourism-intensive economy of the world; the latter examination is pursued further with a national scale analysis of contextual vulnerability in Jamaican tourism and agriculture, referencing to local scale examples of adaptive capacity. By this multi-scalar framework, justice and contextual vulnerability are revealed to be inextricable, and a re-evaluation of how these terms are operationalized in policy is suggested.