This chapter studies interimperial trade from the vantage point of New Granada’s Caribbean ports from the effective instauration of what the Spanish called “free and protected trade” from the mid-1780s to the final years of the independence wars that led to the creation of the Republic of Colombia. Following the paths of ships that frequently crisscrossed imperial political borders connecting New Granada’s Caribbean coasts to foreign colonies, it argues that from the 1780s the Caribbean was turning into a de facto free trade area largely, but not exclusively controlled by Great Britain from the Caribbean commercial center of Kingston, Jamaica. Largely based on previously unexplored Jamaican shipping returns, this reconstruction of New Granada’s commercial networks presents the main routes, ports, types of vessels, frequency of travel, modes of trade (legal and illegal), and commodities traded. Preceded by a brief historical context of the period leading up to the 1780s, the central section of this chapter demonstrates the eighteenth-century progression toward free trade in Caribbean waters and the ways in which the combined effect of war and innovations in commercial regulations made it possible for Great Britain, through its main Caribbean entrepôt, Kingston, to corner most of the benefits to be obtained from interimperial Caribbean trade.