walk the plank – a morbidly playful means of disposing of captives or enemies by extending a plank from the side of the ship and prodding the victim until they stepped off the end, falling into the sea. Historical accounts show that walking the plank did take place, but it was a very rare occurrence.
warp – a (slow) method of moving a ship into the wind by deploying an anchor and then pulling the ship along the attached cable.
weather side - the side of the ship towards the direction from which the wind is coming.
weigh anchor – literally, to lift the anchor out of the water in preparation for moving the ship. By extension, to prepare the ship for getting underway.
wench – a woman, particularly a young woman.
wherry – a small boat used to carry cargo and passengers on rivers and canals, particularly on the Thames.
windward – towards the direction from which the wind is coming.
yard – a spar on a mast from which sails are set.
yardarm – a horizontal pole (a spar) extending from a mast; sails are affixed to yardarms.
ye – a form of the word “you.”
yellow jack – a flag flown by ships, ports, etc. suffering from fever, plague, or that are under quarantine. By extension, the sickness itself (”He died of the yellow jack.”) Ships would be advised to steer well clear of ports flying the yellow jack.
yo-ho-ho – the canonical Pirate expression, apparently originating in Robert Louis Stevenson’s Treasure Island.

