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The Shipman is not someone you'd want to meet in a dark alley in the dead of night. He's the quintessential bad boy – an unsavory type who heeds no law or conscience. If he beats you in a fight, he'll chuck you overboard and send you "home," meaning, to the afterlife. And when the tavernkeeper has his back turned, you'll find him stealing the wine. Despite his criminal nature, though, the shipman's actually pretty good at what he does, calculating tides, navigating the stars, and bringing the ship safely into the harbor with the best of them.
Like the Knight and the Merchant, the shipman is one of the best-travelled pilgrims, having been all over Britain and Spain as part of his job. And about that job: the commercial shipman's trade is one that is only possible because of the rise of the new mercantile class, which needs ships (and the men who sail them) to carry its wares to ports all over Europe. So, with the Shipman, we have yet one more pilgrim who's benefiting as a member of England's new economy.