Archaeological investigations demonstrate that peoples first settled the Caribbean islands approximately 6000–7000 years ago. At least four major, and multiple minor, migrations took place over the next millennia by peoples from Mesoamerica and South America who practised various subsistence strategies and had different levels of technology. For decades, researchers have been interested in investigating how these groups adapted to and impacted insular environments through time. This paper combines archaeological, palaeoecological, historical, and modern biological data to examine the effects of humans on Caribbean island ecosystems using a historical ecology approach. By synthesising a wide range of data sources, we take a human/nature dialectical perspective to understanding how peoples adapted to and modified their environments. The data suggest that earlier foraging/fishing Archaic groups (ca. 6000–3000 BP), who used a stone tool and shell technology and transported few, if any non-indigenous plants or animals, still impacted island landscapes as evidenced by bird and sloth extinctions. As more advanced ceramic making horticulturalists entered the Antillean chain around 2500 BP, there is an observable change to island environments as a result of forest clearance, overexploitation of both terrestrial and marine resources, and growing populations. Palaeoecological and palaeoenvironmental records also suggest, however, that an increased moisture regime during the late Holocene probably led to a decrease in near-shore salinity and heavier sediment and nutrient loads in rivers. These conditions would have been exacerbated by land clearance for agriculture, leading to coastline progradation, increased turbidity, and mangrove development resulting in changes to the availability of resources for humans on some islands. Although prehistoric peoples in the Caribbean were certainly impacting their environments, it was not until Europeans arrived and population centres grew that intensive and widespread degradation of island landscapes and resources occurred. Modern ecological studies, along with historical and archaeological data, indicate that hundreds of species have been driven to extinction or extirpation – many others have significantly diminished in number, especially within the last two millennia.