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The rule of thumb I go for with boats is that the vessel with worse steering has right of way. For instance a freighter has right of way over a sailing boat regardless of direction or wind because the freighter isn't going to be able to change course in any appreciable amount of time.

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Freighters have right of way in constrained waters, but offshore they still need to make way for sailboats.

(Yes, I know colregs is a bit more nuanced than that, but I think this is a decent approximation)

Plastic boats give way to wooden ship, wooden ships give way to metal ships, and nothing gives way anything much smaller than itself - Not the colreg rules, but a good approximation for unskilled crew members. Especially on a wooden ship.

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