It has long since been acknowledged that Aristotle's nautical analogy (DA, 413a8-9) is hard to accommodate within the general framework of his hylomorphic psychology. This paper delves into two ancient accounts of the comparison which prove useful in dealing with its more intractable features. While Alexander of Aphrodisias tried to make sense of the analogy by turning the sailor into a dispositional state of his ship, Philoponus struggled to show how a separate substance can nonetheless behave as the ship's "first actuality". It is argued that neither Alexander's psychological naturalism nor Philoponus' ontological opportunism provide satisfactory readings of the analogy. Philoponus's proposal, however, is preferred, as it preserves Alexander's insights to a greater extent than the other way around. Further, Philoponus achieves this result at a lower theoretical price, since he does not need to distort the most obvious features of the nautical analogy.