This contribution presents an assessment of the potential vulnerabilities to climate variability and change (CV & C) of the critical transportation infrastructure of Caribbean Small Island Developing States (SIDS). It focuses on potential operational disruptions and coastal inundation forced by CV & C on four coastal international airports and four seaports in Jamaica and Saint Lucia which are critical facilitators of international connectivity and socioeconomic development. Impact assessments have been carried out under climatic conditions forced by a 1.5 °C specific warming level (SWL) above pre-industrial levels, as well as for different emission scenarios and time periods in the twenty-first century. Disruptions and increasing costs due to, e.g., more frequent exceedance of high temperature thresholds that could impede transport operations are predicted, even under the 1.5 °C SWL, advocated by the Alliance of Small Island States (AOSIS) and reflected as an aspirational goal in the Paris Climate Agreement. Dynamic modeling of the coastal inundation under different return periods of projected extreme sea levels (ESLs) indicates that the examined airports and seaports will face increasing coastal inundation during the century. Inundation is projected for the airport runways of some of the examined international airports and most of the seaports, even from the 100-year extreme sea level under 1.5 °C SWL. In the absence of effective technical adaptation measures, both operational disruptions and coastal inundation are projected to increasingly affect all examined assets over the course of the century.