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A Pirate's Life Tall Tale guide - Sea of Thieves

A walkthrough of A Pirate's Life, the first chapter of the new Tall Tale, in Sea of Thieves, including the journal locations and commendations guide.

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A Pirate’s Life is the latest Tall Tale in Sea of Thieves. This is a collection of five chapters, the first of which is also called A Pirate’s Life. In this guide, I’ll provide a detailed walkthrough of the first chapter, including the Tales of the Damned and The Crew of the Headless Monkey journal locations and the other commendations and secrets found throughout.

A Pirate’s Life Tall Tale guide

A Pirate’s Life is the first chapter of the new Tall Tale, A Pirate’s Life. This takes players into the Sea of the Damned to rescue someone that is trapped aboard the Ferry of the Damned. The first chapter has ten Journals to find, and several side quests to unlock. Here’s the full list of commendations and a short description of what each entails.

A Pirate’s Life commendations

  • Strange Shores – Navigate Dead Man’s Grotto
  • Tales of the Dead – Rescue the Cursed Captain
  • Waiting for Eternity – Summon the Ferry of the Damned to Sailor’s Grave
  • Raising the Dead – Discover Dougie, the buried pirate
  • Treasure for the Dead – Return Dougie’s treasure
  • A Powerful Thirst – Fill Captain Bone’s tankard with special grog
  • Ship of Thieves – Open the door to the locked ship in Sailor’s Grave
  • Secret of the Grave – Discover the secret of Sailor’s Grave
  • The Prisoner – Release the Ferryman’s Prisoner
  • A Pirate’s Life – Complete “A Pirate’s Life”
  • Tales of the Damned – Discover the Captain’s Journals in Sailor’s Grave
  • The Crew of the Headless Monkey – Discover the Journals of the Headless Monkey’s Captain
  • Mist and Memory – Complete all Commendations in A Pirate’s Life

Starting A Pirate’s Life

sea of thieves a pirate's life guide

To start A Pirate’s Life, begin by voting on the book beside the Castaway. Listen to her story and then sail through the portal that will open up nearby. Look for the glowing green portal between two rocks out in the ocean – there will be a green light shooting up to the sky with clouds swirling above.

Sail through the portal and into the next area. You will be on an automatic ride across the ocean and into another portal on the other side. Once you pass through this second portal, sail to the island ahead of you and weigh anchor – this is the beginning of the Dead Man’s Grotto.

Dead Man’s Grotto

After you make landfall, head deeper into the island, passing through the wrecked hull of a ship. You will spot a statue with a bell, beside which is a cave system. Head inside.

sea of thieves a pirates life dead mans grotto

You will come across a fire with some skeletons and two rowboats leaning up against a gate. Raise your lantern and grab the Flame of Souls. Now use it to light to the lanterns in the rowboats. Go through the gate.

The next area will have more skeletons and three lanterns to light. The first is on the right-hand side being held by a skeleton with a seagull on his head. The next is in the middle of the room – you will need to move the skeleton’s arm to get the lantern. The last is found by following the flowing water to a wrecked rowboat. With the three lanterns lit, the gate will open.

The next area you reach will have some skeletons beside a stool and wrecked crates. The first time you arrive, ghosts will appear to be partying. On your left is a waterfall, go through it to find an oar handle. Take the oar handle up the ramp in the previous room to the top where it can be used to repair a door lever. Repair it and use the lever to open the door.

In the next room, work along the right-hand wall, being careful not to fall into the mist. If you fall in, walk back to the beginning and try again. Go across the running water and into the next area.

This next area has some wooden obstacles to traverse. Use your lantern to light the lantern on the crate to summon the ghostly images. Now, go up to the anchor and turn it to lower the drawbridge.

Go across the drawbridge and use the pulley to raise a platform to reach the other side. Walk along to the end of the path to find another lantern that you must light. Wait for the ghosts to row up, at which point the next drawbridge will lower.

In the next area will be a pile of gold. Use the path around the perimeter to reach a series of platforms. Jump across them to reach the other side.

The next room has a ladder on the right, climb it and use your cutlass to cut the rope, causing a platform to fall down. Climb down the ladder and run across the platform to find a pulley and a mast. Use the pulley to pull the mast toward you. Jump on it and ride it to the other side. Cut the next bit of rope to drop another platform down and jump across. Slide down the water slide to the next area – Sailor’s Grave.

Sailor’s Grave

Sailor’s Grave is where you will spend the majority of your time, completing the various commendations and finding the 10 Journals. As a word of warning, the journals must be collected before taking the Cursed Captain’s skull to its final location in the ship with the red sails. You can use the following links to jump to the journal locations, which are below:

The first lot of journals (Tales of the Damned) are found throughout the main area and can be collected as you follow the story. The journals for The Crew of the Headless Monkey are in a specific location that is locked unless you complete all the side quest commendations, which are listed below.

sea of thieves a pirate's life chapter 1 sailors grave

Begin by descending the mountain to a locked gate. On the left will be a brazier that you must light with your lantern, this will unlock the gate and raise the bridge.

Follow the path to the center of the area, you should begin to hear the Cursed Captain talking. You first task will be to rescue the Cursed Captain.

Use the stairs below the captain to reach the top of the wreckage – you will go around the back of the ship a bit. Cross the lashed together masts to the other side and then run up the bowsprit and into the ship that’s smashed on the rock. Drop down into the water and swim to the other side.

You will come across a platform with a pulley system. Use the pulley to lift yourself up to the next level. This platform contains another pulley as well as the locked door of the ship – this last bit is for later. Use the next pulley to raise a pallet of crates and barrels. Jump across to the next level.

Another pulley will be on the right-hand side. Use them to move two platforms across the gap. You must jump across them to reach the other side. If you fall down, turn around and use the platform-pulley system you used to reach the top.

Climb the bowsprit to the cage. You will need to use a cutlass to cut the rope, lowering the cage to the ground below. With the cage lowered, you will need to find the cage key.

The cage key is found in the tavern, which is to the side of the area. Enter it and go up behind the bar to find a pulley. Use the pulley to lower the chandelier, which has the key on it. Grab the cage key and take it back to the Cursed Captain and unlock his cage.

At this point, the Cursed Captain will direct you to go to the lighthouse, however, now is a good time to do all the other side quests around Sailor’s Grave. So let’s do that.

Find Dougie

sea of thieves a pirates life poor dougie

Now, you will need to find Dougie, the buried pirate. Head back into the tavern and into the room up behind the bar. There will be a map on a table – use your lantern to light the candles. Ghosts will appear and point at a red X on the map. You will need to head to this location.

sea of thieves a pirates life raising the dead

To find the X, head towards the ship with the red sails and continue along the path until you find a hole in the ground with some gold around it. Follow the trail of gold coins to a broken ladder, to reach the top use the mast that’s fallen down.

The coins will lead you back down the rocks and toward a wreckage beside the tavern. There will be a hole in the ground, dig here to unearth Dougie. Light his lantern to bring him to life.

Find Dougie’s treasure

sea of thieves a pirates life treasure for the dead

Next, you will need to find Dougie’s treasure, this begins with finding the treasure map. Head back toward the center of the area, where the Cursed Captain’s cage is located. On the side of the area will be a boardwalk heading around the rocks to the front of the broken ship. Open the ship door and head inside to find a skeleton in a bed.

Use the pulley on the left-hand wall to open the curtains. On the right is a door to the balcony that has three torches to light, two beside each other and one around the corner.

sea of thieves find dougies treasure

Head back to the bed and move the skeleton’s arm to see through its magnifying glass. You will see a red X on the map (it’s outside the tavern).

Go back outside and to the front of the tavern. The place to dig is a few feet from the tavern’s wooden planks. Dig up the chest and now take it back to Dougie. Hold the chest and interact with Dougie to place the chest on the ground. Dougie will give you his key to unlock it.

Use Dougie’s key on the chest to open it. Grab Poor Dougie’s Medallion and head back to the center of the area.

Skeletons playing chess

sea of thieves a pirates life a Powerful thirst skeletons playing chess

The next task to complete is the commendation, A Powerful Thirst. This is achieved by going to the two skeletons that are playing chess. They are found in the back of the broken ship, behind the Cursed Captain’s cage. You must also do this commendation if you want to do Ship of Thieves and Secret of the Grave.

sea of thieves a pirates life captain bones special recipe required

You can leave Dougie’s medallion here. Light the candle using your lantern. Watch the skeleton’s move, at one point the one on the right will try to drink but will be out of grog. You will now need to find Captain Bones’ Special Recipe.

To find Captain Bones’ Special Recipe, go from the Cursed Captain’s cage back to the pulley lift. This is found through an alleyway lit by torches. Go through the alley, use the pulley lift, and jump across the crates. 

sea of thieves captain bones special recipe

You will now be looking for a small hole in the side of the rock that can be jumped into from the small platforms. Jump into the cave, grab the bottle of grog, unlock the gate, and return to the chess-playing skeletons.

sea of thieves a pirates life ships key

Use Captain Bones' Special Recipe to fill the skeleton’s tankard. After the skeleton explodes, you will need to put Poor Dougie’s Medallion on the table as the buy-in. Next, put the Cursed Captain’s skull on the body. When you’re able to, grab the Ship’s Key from the table. This is used to unlock the ship at the top of the pulley lift.

The locked door – Ship of Thieves

sea of thieves a pirates life ship of thieves

After completing A Powerful Thirst, getting Poor Dougie’s Medallion, and claiming the ship’s key, you’ll be able to unlock the locked door you found at the top of the pulley lift. Doing this unlocks Ship of Thieves.

sea of thieves a pirates life ship of thieves

Take the Ship’s Key to the center and go back down the alleyway to the pulley lift. Use the key on the door to unlock it. Go inside and grab the coins from the floor. Head out the back and use the pulley on the right-hand side to turn the sails – this will let you use the lighthouse to light the brazier.

With that out of the way, you can continue to the lighthouse.

Sailor’s Grave – The Lighthouse

sea of thieves a pirates life lighthouse

With all the previous tasks done, you’re in a good spot to continue to the lighthouse. Make your way there with the Cursed Captain and cross the bridge. Climb to the top of the lighthouse and place the Cursed Captain on the headless skeleton.

Now, climb the ladder to the very top and use your lantern to light the brazier. One wheel will turn the beam of light and the other will tilt the light up and down.

Turn the light around and light up the brazier you revealed by moving the sails behind the locked ship door. This is critical in acquiring the Journals of the Headless Monkey’s captain. You can now safely light the other three braziers out across the water. After the Cursed Captain is ready to go, grab him and head back down – you should now go and get the Journals of the Headless Monkey’s captain.

Sailor’s Grave – The ship with the red sails

sea of thieves a pirates life ship with red sails

After you’ve gotten all the journals, you can now take the Cursed Captain to the ship with the red sails. He’ll open the door for you, granting you access to the inside. Be sure to pick him up and take him with you. The final journal is also inside in the captain’s quarters.

Pop the Cursed Captain’s skull on his body and then grab the Cabin Key from him after his speech. Use it to unlock the back door. Walk through the next ship, jump into the rowboat, and row straight until you see the Ferry of the Damned. Dock your rowboat to its stern, get onto the ship, and climb the ladder to reach the deck.

The Ferry of the Damned

Once aboard the Ferry of the Damned, use your lantern to light the Well of Fates. Once it explodes, head below deck.

Light the lantern beside the door to unlock it. In the next room, close the sarcophagus to reveal a torch, light both torches in this room to unlock the door. Go into the next room and down the stairs. Head to the other side of the room and interact with the dog to get the keys. Unlock the door to free the prisoner. Now, follow the prisoner back to the top of the ship.

sea of thieves a pirates life guide

All that’s left to do now is to defend the Ferry of the Damned. Use the cannons to fire upon the Flying Dutchman. Replenish your fruit and cannonballs using the resource barrels below deck. At some points, Ocean Crawlers will come aboard, defeat them and keep up the fight. Continue going until the fight ends and the Ferryman talks to you once more. Go through the door to get back on to your ship. Sail it out until you return to the Sea of Thieves.

A Pirate’s Life Journals

There are ten journals to be found in the first chapter, A Pirate’s Life. Five of these journals are written by the Cursed Captain and are all found in the Sailor’s Grave. The other five are from the captain of the Headless Monkey, and are found in a secret area.

Tales of the Damned - Journals

sea of thieves a pirates life tales of the damned journal 1

The first journal is called The Haul of a Lifetime and it’s in the tavern, at the very top on a table.

sea of thieves a pirates life tales of the damned journal 2

The second journal is called Dissent in the Ranks and it’s in the room with the skeleton in the bed, on the bedside table.

sea of thieves a pirates life tales of the damned journal 3

The third journal is called Off the Edge of the Map and is found on a table near the two skeletons playing chess.

sea of thieves a pirates life tales of the damned journal 4

The fourth journal is called Strange, Yet Familiar and is found at the top of the lighthouse on a small bookshelf by two skeletons.

sea of thieves a pirates life tales of the damned journal 5

The firth journal is called Lights Out and it is found in the captain’s quarters of the Cursed Captain’s ship, on a bookshelf.

The Crew of the Headless Monkey – Journals

The journals of the Headless Monkey’s captain are found at the start of the area, all around the shipwreck of the Headless Monkey ship. You will need to have completed all the other side quests in the area in order to move the sails behind the locked door on the ship. With the sails moved, you can use the lighthouse to light the brazier.

To reach the Headless Monkey journals, backtrack past the Cursed Captain’s cage, sticking to the northern side. You will come across a now-raised bridge, granting you access to a previously inaccessible location. Cross it to find a shipwreck of the Headless Monkey. Grab the key from the skeleton at the wheel to unlock the door in the side of the ship.

sea of thieves a pirates life the crew of the headless monkey journal 1

The first journal is called Somewhere in the Caribbean and is by the wheel of the ship.

sea of thieves a pirates life the crew of the headless monkey journal 2

The second journal is called Raising the Mad Monkey and is in front of the wheel, on the mast.

sea of thieves a pirates life the crew of the headless monkey journal 3

The third journal is called A Headless Monkey and is near the mast in the center of the wreck.

sea of thieves a pirates life the crew of the headless monkey journal 4

The fourth journal is called Fresh Waters and is in the bookshelf behind the locked door.

sea of thieves a pirates life the crew of the headless monkey journal 5

The fifth journal is called A Fateful Pursuit and is on the table beside the map behind the locked door.


A Pirate’s Life is the first chapter in the similarly-named Tall Tale in Sea of Thieves. By completing the above steps in the given order, you should finish the chapter with all the commendations unlocked and all your rewards. The main challenge will be reaching the Headless Monkey ship – if you can do that you’re all set. Be sure to check out the Shacknews Sea of Thieves Guide for more tips and content to help you get your sea legs.

Guides Editor

Hailing from the land down under, Sam Chandler brings a bit of the southern hemisphere flair to his work. After bouncing round a few universities, securing a bachelor degree, and entering the video game industry, he's found his new family here at Shacknews as a Guides Editor. There's nothing he loves more than crafting a guide that will help someone. If you need help with a guide, or notice something not quite right, you can Tweet him: @SamuelChandler 

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