The COVID-19 pandemic has been an unprecedented economic shock to Caribbean countries, most of which depend heavily on Tourism and its linkages to a wide range of sectors. The World Tourism Organization reported 2020 as the worst year on record. Destinations worldwide welcomed 1 billion fewer international arrivals in 2020. In this collection, the contributors seize the opportunity to rethink, discuss, and address the issues and challenges to Caribbean Tourism both before and since the pandemic, not least of which is climate change. The increasing frequency and intensity of natural disasters in recent years, coupled with the devastating effects of the pandemic and the containment measures adopted by governments, has made crystal clear the importance of addressing the sustainability of Caribbean Tourism. Recommendations are made for critical remedial actions to accelerate post-COVID-19 tourism recovery and foster enhanced resilience, including the identification of new and under-exploited tourism niches. Responsive to the current and future needs of the industry, this collection suggests remedial policy measures to tackle both the challenges posed by the COVID-19 pandemic, as well as historical socio-cultural issues, which have hampered the pre-pandemic tourism industry.