Caribbean islands, like other Small Island Developing States (SIDS), are at the center of the vulnerability debate as current climatic trends predict elevated sea levels and increased frequency of storms, leading to significant challenges for local communities. Caribbean islanders have been exposed to climatic challenges since the initial occupation of the archipelago between five to eight thousand years ago. They have been continually confronted with severe droughts, tropical cyclones, extreme wave events, sea-level changes, and the accompanying impacts. The various phenomena have stimulated island residents both to anticipate and respond to such events, adapting their lifestyles and socio-cultural and political structures and ties across the region over time. In this article, we innovatively combine archaeological and palaeoenvironmental data with longitudinal coastal-erosion data and ethnographic data to further develop and promote sustainable local strategies to mitigate the adverse effects of climate change and increasingly frequent and violent weather events on small-island settings. To find proxies, we first look into the region’s pre-colonial archaeological record. Second, we delve into predictive modeling and the current and future climatic challenges for heritage sites and local coastal communities, as well as related collaborative heritage mitigation efforts. Third, we discuss the contribution of traditional knowledge practices to climate change adaptation. The results show how the long-term perspective and multidisciplinary approach adopted here may lead to realistic solutions to seemingly intractable problems. They also reveal how collaborative projects involving all stakeholders on an equal basis in all phases of research have become a top priority in climate change mitigation and heritage safeguarding.