Sea of Thieves is getting its biggest and most exciting update yet. Tied in with Season 3, the new “A Pirate’s Life” update will see this swashbuckling world cross swords with Disney’s Pirates of the Caribbean film franchise. Not only will this season revolve around a brand new storyline, but it will introduce a host of changes to the game’s world. Along with new story content, players can complete challenges tied to the new Tall Tales. Finishing all of these will unlock new cosmetics for your pirate, so it’s definitely worth beating as many as possible. Most of these are tied to a secret quest revolving around Poor Dougie’s key, chest, medallion, tankard, and opening the locked ship.
(Keep in mind you need the Cursed Captain’s head to finish this side-quest so do not put his head on the final skeleton body!)
How to Complete Poor Doguie’s Quest
Raising the Dead – Poor Dougie’s Chest Key Location
When you arrive in Sailor’s Grave, make your way to the docks on the left near the large lighthouse. You will see a small path leading underneath the dock where there are some barrels and crates lying around. Take out your shovel and begin digging where the trail of gold coins ends. You will unearth Poor Dougie who has a chest key tied around his neck. Dougie will request that you find his treasure chest, which is thankfully not that far away!
Treasure for the Dead – Poor Dougie’s Chest Location
Now that you’ve unearthed Poor Dougie, head towards the tavern. To your left, you’ll see a small wooden path leading towards the back of a ship where to skeletons are playing chess. While facing the path to the chess-playing skeletons dig to the left of a small pointed rock (shown above). You’ll discover a chest that you can bring to Dougie, who will give you his key to open it. Inside is Dougie’s Medallion, which you’ll need to progress this side quest.
A Powerful Thirst – Captain Bones’ Special Recipe Location
Take Poor Dougie’s Medallion and bring it to the chess-playing skeletons. Set it on the table near them for now and make your way to the pully system you used to reach the Cursed Captain’s head. Stop when you arrive at the two suspended panels you can move with the pullies. Arrange them so they are roughly around the middle, but close enough that you can jump to them. On the right, you’ll find a small cave that you can jump into from these panels. Inside on the floor to the right is Captain Bones’ Special Recipe. Grab the bottle and bring it to the skeletons by the chess table. Light the candle with your lantern and then give the skeleton on the right side the drink.
Ship of Thieves – Unlocking the Locked Ship
Upon giving Captain Bones his drink, the skeleton’s head will explode. The Cursed Captain will suggest letting him take the captain’s place, but you will need to buy into the game first. Take Poor Dougie’s Medallion and place it onto the table when indicated. Once this is done, pick up the Cursed Captain’s head and stick it on the body of Captain Bones. After he wins the game, take the key back to where the pully elevator is and use it to open the door to the locked ship. Inside you’ll find stacks of gold which you can interact with and add a few thousand into your inventory for all your legwork.
Upon completing Poor Dougie’s questline you will be able to access the Secret of the Grave and Headless Monkey Journal commendations. Here’s my guide on these separate commendations and journal locations so you can 100% this Tall Tale.