This essay considers the teaching of Italian in early modern England by looking at the texts, methods, and individuals involved. It considers some ways in which audiences not conforming to the traditional stereotype of the ‘Italianate gentleman’ shaped Italian pedagogies across the period, and analyses little-known print and manuscript texts that shed light on these audiences. It asks how, if at all, English students of Italian might have encountered the debates of the questione della lingua, moving from the evidence provided by pedagogical texts to the experiences of travel and Anglo-Italian personal relationships. Both were crucial to shaping English readings of the questione and, in at least one case, to the formulation of an Italian-inflected contribution to debates on the English language. Lastly, it looks at how ideas of ‘correct’ or prestigious written and spoken Italian were constructed for English learners of the language, both in pedagogical texts and in individual encounters with the Italian peninsula.