So I sailed all the way to the southern edge of the map for a Reapers Chest.
And it de-spawned, re-spawned in the far NW corner of the map.
So I beat into a headwind and those annoying waves that turn the ship all the way up there and picked it up.
Sailed almost al the way back to Reapers and get Krakened :(
Sometimes ya just can't win for tryin!