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This essay aims to provide a concise account of the celebrated encounter between two titans of seventeenth-century thought, the English poet John Milton and the physicist and astronomer Galileo Galilei. The encounter, which later became the subject of literary compositions and pictorial depictions, has long been the subject of heated philological and historical disputes, aimed at determining its veracity and nature. A strand of modern criticism has described the encounter as apocryphal, most likely an invention of Milton himself. Reanalyzing the whole issue, using primary sources and later interpretations, in this examination we firstly argue for the veracity of the encounter. A second and more substantial line of reasoning developed here examines the role played by Galileo’s figure in the Miltonian corpus, ultimately leading us to an assessment of Milton’s personal judgement of the new science proposed by the Pisan scientist. In order to achieve a more complete understanding of the astronomical references encountered in Milton’s production, they are examined from the perspective of the culture and knowledge of the time in which they were enunciated, of earlier literary examples and even of modern scientific notions.