This paper investigates the fate of Greek wine in England in the late Middle Ages and the early modern period. It will be explored how Cretan wine was challenged by Spanish and Atlantic wines and eventually even replaced after the Ottoman conquest of Crete. The hypothesis is that the histories of Cretan, Spanish, Atlantic and Port wines are entangled for they all catered to a fairly stable consumer's taste for sweet wine. I will argue that interventions by political authorities, in the form of privileges, free trade areas, customs and monopolies mattered in this process because they changed incentive structures. For even if actors do not comply with regulations, they still have to cope with them; using opportunities and avoiding costs, which from the legislators' perspective might often be fraud.