I've yet to see the current holiday shop stocked with anything - is my luck really just that bad? Every time I check it, it says it was stocked four or five minutes ago, but is empty. Is anyone else having this problem/is there some trick I should be using to catch it stocked?

It stocks approximately every six minutes. Meaning when you see it say "stocked five minutes ago," you should stay and keep refreshing because it will be stocked shortly.

It only gets a little stock at a time, and it goes quickly, so you have to be there at the minute of restock or you won't get anything.

If you have access to Carl Quests you have a slight chance of getting a new or retired item from that shop from his quests.

The Mystery Box once had the shop in it's rotation once, if you check the box every day it could happen again, we're all kinda hoping for it actually lol.

The ocean depths vending machine gives out pirate stuff too.

ahh thanks I was finally able to nab some things! yeah I've been doing the Carl quests but I haven't gotten much :( thanks I'll check that!

any quest that drops items has a chance to give you a prize from the pirate shop: Blue Building, Cursed, Library and Pete

Wizard and Quentin also drop items, but they don't pull from the regular shops so they can't give out pirate items.

oh cool thanks!