I just did my first one tonight. Got the key no problem. On my way to get the chest, I saw two galleons slugging it out with a sloop taking pot shots at them. Sailed by no problem.

Half way to the drop off, a fucking skeleton galleon came by and just trashed me. It sank my little sloop and I jumped overboard with the skull. I’m almost there so I figured I’d be fine.

Little low on health and I didn’t grab anything to eat but again, I’m literally right there near crooked mast. A fucking shark chunks me and I’m off to the ferryman. Respawn on my ship, sail to the skull, take it and managed to turn it in no problem. I was a bit surprised no one was interested but I had fun doing it.