Engraved nautical illustrations at nineteenth-century sites in The Bahamas are generally associated with African-Bahamian lifeways. Previous studies of the artistic tradition have advanced arguments that are plausible, but conceptualizations of the phenomenon as graffiti establish a priori assumptions that require critical examination. Credible comparative analysis also demands a secure empirical foundation. Recent investigations at Cat Island, involving the survey of heritage sites related to the Loyalist plantation period (1783–1838), have revealed over 900 ship images incised into the stucco surfaces of masonry ruins. This large sample of drawings permits a more detailed characterization of the Bahamian art form than has hitherto been reported. A significant proportion of imagery emulates the style of sail plan diagrams used by shipwrights, and depictions of masts and rigging provide insights into iconographic context. Survey data also shed light on the spatial distribution of the engravings, including degree of difference between interior and exterior locations, the role of building size, and wall height. Although the precise meanings of nautical symbolism are elusive, findings from Cat Island challenge the prevailing view that ships are the exclusive recurring motif in the archipelago. Recently identified depictions include watercraft accompanied by marine fauna and a human figure. Given existential threats, research is employing photogrammetry to preserve ship drawings within digital 3D models of architectural features.