Five wooden sculptures from the pre-contact Caribbean, long held in museum collections, are here dated and given a context for the first time. The examples studied were made from dense Guaiacum wood, carved, polished and inlaid with shell fastened with resin. Dating the heartwood, sapwood and resins takes key examples of ‘Classic’ Taíno art back to the tenth century AD, and suggests that some objects were treasured and refurbished over centuries. The authors discuss the symbolic properties of the wood and the long-lived biographies of some iconic sculptures.