Ahoy there, fellow pirate! 🏴‍☠️ If you’ve been sailing through Sea of Thieves: A Pirate’s Life and thought, ‘What’s up with that skeletal guy under the docks?’ — well, you're in for a treat. I just wrapped up the Raising the Dead side quest, and not only did I get Poor Dougie’s Medallion, but I also unlocked a chunk of that sweet, sweet Yo Ho shanty everyone’s been humming at the outposts. Let me spill all the rum-soaked details, pirate to pirate.

Honestly, when I first stumbled into Sailor’s Grave, I was just chasing Jack Sparrow’s chaos. But then I noticed a trail of gold coins… and curiosity got the better of me. If you’re anything like me, you can’t resist a good hidden treasure — especially when it leads to a talking skeleton with a tragic backstory. And let’s be real, who doesn’t want a medallion that lets you play chess with the Cursed Captain’s head? 😂

Here’s exactly how I did it, step by step, so you don’t waste a single cannonball of effort.

Where to Find Poor Dougie 🦴

First things first: where in the Sea of Thieves is this bony buccaneer? He’s chilling in Sailor’s Grave, the shipwrecked town that’s part of A Pirate’s Life. Specifically, head under the docks near the lighthouse. There’s a tiny path leading under the wooden planks — I nearly missed it because I was too busy ogling the ghostly architecture. Look for the trail of gold coins glinting on the ground; follow it and you’ll spot a mound of dirt begging to be dug.

Pro tip: Bring a shovel (I forgot once and had to row back to my sloop — don’t be like me). Start digging at that mound. After a few scoops, you’ll uncover Poor Dougie himself. But he won’t spill his secrets right away. Light the lantern beside him, and suddenly he’s the chattiest skeleton in the Caribbean, spinning a tale of betrayal by his own crew. 💔

See that lantern? It’s the key to making him talk. I actually spent a full minute just staring at him before I realized I needed to light it. Hashtag pirate problems.

The Treasure Hunt: Two Ways to Find Poor Dougie’s Chest 🗺️

Once Poor Dougie begs you to find his treasure, you’ve got a choice: solve the puzzle like a true legend, or brute-force your way with a shovel. I’ve done both, and they each have their charm.

The Puzzle Route (for the Sherlock Holmes pirates)

This one’s so atmospheric I actually screamed when a skeleton jumped out at me. No, wait, that didn't happen — but it could have.

1. Head to the split shipwreck in Sailor’s Grave. Enter the side that leads to a broken cave and hull.

2. Follow the wooden path until you reach a door. Open it.

3. Inside, you’ll see a skeleton in pajamas lounging on a bed (relatable). Use the pulley to reveal a second skeleton holding a magnifying glass.

4. Go upstairs and light the three lanterns. The light will make the magnifying glass move and — ta-da! — reveal the exact digging spot on a map or through the glass itself (depending on how you interpret the spooky magic).

It’s honestly such a cool little puzzle. I love how Sea of Thieves rewards you for paying attention.

The “I Just Want the Loot” Route 💰

If you’d rather skip the drama, head toward the tavern. Face the tavern and check the left side of the path. That’s where the treasure is buried. It’s not far from Poor Dougie at all — maybe a thirty-second sprint.

Grab your shovel and dig. You’ll unearth a chest that looks like it’s seen better centuries. Bring it back to Poor Dougie, who will hand over the key hanging from his bony neck. Use it to unlock the chest, and inside you’ll find Dougie’s Medallion. Easy loot, right?

That chest design is just chef’s kiss. I wanted to keep it as ship decor, but alas, the quest demands it.

What to Do with the Medallion: Powerful Thirst and More 🧩

So why should you even bother with this side quest? Is it just for the gold? Partly — but there’s a deeper purpose. Dougie’s Medallion is a key item in the Powerful Thirst side quest, which runs parallel to Raising the Dead. Completing both is necessary to unlock that glorious “Yo Ho (A Pirate’s Life for Me)” shanty at the end of all five Tall Tales. Trust me, it’s worth it for the jam sessions alone.

Here’s a quick rundown of how to use the medallion:

• Find the skeletons playing chess near the tavern. Light the candle on their table with your lantern to get them talking. They’re parched and want a drink — specifically Captain Bones’ Special Recipe.

• Follow the clues to brew the drink (I won’t spoil that part entirely, but it involves some spooky ingredients).

• Finally, place Dougie’s Medallion on the chess table. This will attach the Cursed Captain’s head to a skeleton body, letting you play a game of chess — and, more importantly, open a vault stuffed with gold.

Is it a little morbid? Absolutely. Is it hilarious? 100%. I almost lost the chess game but walked away with more coins than I knew what to do with. 💸

A Few Pirate Tips from My Own Misadventures ✨

• Light everything. Seriously, if a lantern or candle looks interactive, light it. That’s how you trigger half the quests in this game.

• Don’t forget to bring the medallion back to the chess table. I accidentally sold a chest not realizing the medallion was still inside once, and had to redo the whole thing. Learn from my pain.

• Enjoy the story. Poor Dougie’s tale is surprisingly sad, and the environment storytelling in Sailor’s Grave is top-notch. Take a moment to explore the shipwrecked town — you’ll find journals, easter eggs, and maybe some extra loot.

Now, in 2026, Sea of Thieves is still going strong with new seasons and adventures, but these classic Tall Tales remain some of the most memorable content Rare has ever created. If you’re sailing through A Pirate’s Life for the first time or returning after a long hiatus, don’t skip the side quests. They add so much flavor — and in the case of Poor Dougie, a genuinely fun puzzle.

So what are you waiting for? Hoist the sails, grab your shovel, and go dig up a talking skeleton. And when you finally place that medallion on the chess table, I’ll bet you’ll be grinning like the Cursed Captain himself. Fair winds and following seas, matey! ⚓️🦜

Data referenced from HowLongToBeat helps contextualize how side objectives like “Raising the Dead” can meaningfully extend a Sea of Thieves: A Pirate’s Life session—especially for completion-minded crews who stop to chase coin trails, solve lantern-and-magnifying-glass puzzles, and loop back to use Dougie’s Medallion in parallel tasks such as “Powerful Thirst” rather than rushing the Tall Tale’s main beats.