The archaeology of the post‐Emancipation Caribbean remains relatively understudied. The collapse of the industrial‐scale sugar plantation systems of the islands in the early 19th century saw a radical re‐organization of socio‐economic life. A new corpus of consumers was created, eking out a living on the margins of island society, but never quite liberated. This period sees the emergence of an Afro‐Caribbean maritime culture focused upon shipbuilding, fishing, turtling and whaling, the latter a particular feature of the eastern Caribbean (Windward Islands). The archaeology of whaling communities, is relatively well understood from the perspective of North America, Australasia and Europe, but less so in the Caribbean. Using two case studies based upon recent excavation and survey work, this paper sheds light on a distinctive maritime cultural response in the post‐emancipation Eastern Caribbean world.