This contribution offers a broad overview of the material evidence (archaeology) of multiscalar approaches to human–water interaction on the islands of the Caribbean from the precontact period up to the present day (i.e., ca 3000 BC–AD 2000). Precontact indigenous hunting/gathering/fishing and early farming peoples relied upon water management technology to mitigate problems of water shortage and drought (and indeed problems of excess of water, flooding). Further, archaeological work linked to other interdisciplinary approaches can demonstrate that their perception of water use was also linked to symbolic behavior as well. After AD 1492 as the newly Europeanized Caribbean islands industrialized in response to developing intensive sugar monoculture systems, more emphasis was placed upon extensive and complex water storage and irrigation works that at once reflected differing environmental demands of island ecologies, and also residual cultural traditions of the European colonial powers regarding water management and conservation. It will be demonstrated that within these socially and culturally diverse islandscapes, novel symbolic approaches to water also emerged, reflecting these many and varied roots of Caribbean cultural traditions. WIREs Water 2017, 4:e1235. doi: 10.1002/wat2.1235 This article is categorized under: Science of Water > Water and Environmental Change Human Water > Water as Imagined and Represented