This dissertation examines colonial smuggling in the mid-eighteenth century between British North America and the Caribbean from the operational perspective of the captains and crews of the coastwise merchant vessels engaged in that trade. In doing so, this work seeks to recast these particular smuggling mariners as agents of a unique professional maritime skillset, whose expertise created paths for upward mobility in their communities and careers. Returning the mariners’ skills and core occupation to their historical identity refines and corrects arguments about mariners’ perceived attitudes toward the Navigation Acts, smuggling, and the American Revolution. Focusing on operational skills differentiates the coastwise mariners engaged in the trade between British North America and the West Indies trade from trans-oceanic mariners, navy crews and other shoreside maritime professions during this period. The success of the coastwise smuggling trade further situates these smuggling mariners in the eighteenth-century historiography of advances in navigation, ship construction, and rigging design.