A Pirate's Life (quest)

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Disambig.png This article is about the Tall Tale. For the story arc of the same name, see A Pirate's Life.
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A strange Castaway warns of danger, both to the Sea of Thieves and the pirate’s life itself...

A Pirate's Life is the first Tall Tale in the A Pirate's Life Arc. The Tale Book can be voted for at the Castaway's Camp on any Outpost. The Tall Tale can be cancelled by voting at the Ship's Voyage Table.

The details on the location of the Tale Book, related Commendations and unlockable Cosmetics are all presented in the Tall Tales Reputation Menu.

The reward for completing the A Pirate's Life Tall Tale is 8,000 Gold.

This Tall Tale must be completed in order to access the second Tall Tale, The Sunken Pearl.



The Castaway

Can you feel it? The ill wind, blowin' from beyond the horizon…
These wild waters, them call to me.
They've seen much to chill the blood… A deep hunger, a heart of fire…
But them always promise the freedom of the sea.
Now though, a new danger is comin' on the tides.
Already, it change this world to his likin'.
An' if what it wants can't be found, it will take… everythin'…
Want to know its name…?
Mmm… The one who brought this ruin lie in iron below the feet of the Ferryman, trapped for all forever in the Sea of the Damned.
Nobody but its captain may tread below the deck of that ship.
That means to learn the truth with your own eyes, you'll have to stow away.
But if the Ferryman, him catch you, your destiny might end there…
Still listenin', hmm? Then listen close!
All you think you know about your life and death is only the beginning.
With your heart still beatin', you will see those cursed chores with new eyes… when you raise up the Flame of the Souls!
All I can do is show you the way…

(The Castaway casts a spell, opening a Tunnel of the Damned)

I travelled to another world, an' now you will do the same…
Take these words for the journey.
If you read them right, them whisper what has been – and what is yet to be.
Whispers to help you save a pirate's life…
Now make sail!
The door is open. The prisoner is waiting. And our time is tricklin' away…

After the Castaway delivers the dialogue, set sail through the portal she has opened, and you will find yourself and your ship in the Tunnel of the Damned.

Warning: You cannot bring treasure with you into the Sea of the Damned. Your worldly possessions must stay behind. So, if you’ve got something worth selling, do so before you sail through that portal!

Tunnel of the Damned

In the Tunnel of the Damned, your ship will sail on its own will. Also, you will be met with a variety of ghostly apparitions. First, you’ll be met by a ghostly parrot. Then, you’ll see rowboats approaching, each seemingly ferrying a soul. Then you’ll also see shadowy ships in the distance, while ghostly pirates appear and disappear on your ship. Near the end, you’ll hear an ominous ghostly voice intoning cautionary advice, which is the familiar voice from the Pirates of the Caribbean ride.

Ghostly Parrot

Dead men tell no tales. (squawk) (whistles)
Shiver me timbers. (squawk)
(squawk) Trinkets and coins. Trinkets and coins. (squawk)

Ghostly Voice

Ye come seekin' adventure and salty old pirates, eh?
Sure, ye've come to the proper place.
But keep a weather eye open mates, and hold on tight...
...with both hands, if you please.
There be squalls ahead, and Davy Jones waiting for them what don't obey.

After exiting the Tunnel of the Damned, you will emerge in a strange new land within the Sea of the Damned.

Strange Shores

After not having control of your wheel, it is now time for you to take the wheel, and dock your ship at the shores of an island of jagged rocks and palm trees.

Enter into the cave, and begin your journey through Dead Man's Grotto. Along the way, the ghostly voice from the Pirates of the Caribbean ride greets you with lines. While in the Grotto, you will receive the Flame of Souls, which you will use to light lanterns and braziers throughout the tale.

Ghostly Voice

Burn, bright accursed light, upon tales of old and ill deeds, long past...

(After passing through the gate)

DEAD... MEN... TELL... NO... TALES...

(After lighting all three lanterns in this area)

DEAD... MEN... TELL... NO... TALES...

(After entering the shipwreck area)

Ghostly Voice

If ye be brave enough to proceed, the curse of Dead Man's Grotto awaits ye...

(After leaving the shipwreck area)

Ghostly Voices

(Distant Singing) Yo ho, yo ho, a pirate's life for me...

(After proceeding up the cave)

Ghostly Voice

DEAD... MEN... TELL... NO... TALES...

(After passing through the door)

No fear have ye of evil curses, says you?
Arrrgh... Properly warned ye be, says I
Who knows when that evil curse will strike the greedy beholders of this bewitched treasure?
DEAD... MEN... TELL... NO... TALES...

(After lighting the lantern on the crate)

(Ghostly rowboat appears travelling down the stream)

Ghostly Voice

Sit closer together, and keep your ruddy hands in board! That be the best way to repel boarders!
And mark well me words mateys... Dead men tell no tales!

(After lighting the lantern by the drawbridge)

Ghostly Voice

DEAD... MEN... TELL... NO... TALES...

(After entering the treasure room)

Ghostly Voice

The truth lies before ye... In this place, dead men'll always have tales to tell...

(After crossing the dropped bridge)

Ghostly Voice

Perhaps ye knows too much... ye've seen the cursed treasure. Ye know where it be hidden
Now proceed at your own risk. These be the last 'friendly' words ye'll hear
Ye may not survive to pass this way again...

Ghostly Voice

DEAD... MEN... TELL... NO... TALES...

After emerging from Dead Man's Grotto and lighting the beacon, you may make your way into Sailor's Grave.

Tales of the Dead

Upon arriving in Sailor's Grave, you must light a brazier to open the gate to the shipwreck town. Upon entering, you will hear a voice calling out to you. This is the Cursed Captain, a friendly skeleton whose head has been locked in a cage. He will show you the way up to him, from which you will drop his cage to the ground. Afterwards, he will tell you where the key to the cage is, and you can free him. He will be your guide through Sailor's Grave, showing you interesting locations throughout the town. When you are ready, he will direct you to the lighthouse, where you will light a beacon to call the Ferry of the Damned to you.

Deep in the Caribbean

Light the beacon (with the lighthouse) between the two rotatable sails on the destroyed ship in the town, a bridge begins to lift unveiling a new area within Sailor's Grave. The Headless Monkey shipwreck is a reference to the game series Monkey Island. The music playing in this area is a version of the Monkey Island game theme. There are five Headless Monkey Journals to find in and around this wrecked galleon. Two of which require the Headless Monkey Key found by the helm of the ship, to open the door to the Captain's Cabin. Entering the Headless Monkey area for the first time will reward pirates with the Secret of the Grave Commendation. This chapter is optional and is not required to continue with the Tall Tale.

The Damned Stowaways

Upon the Ferry's arrival, the Cursed Captain will take a key in his mouth, and show you to his ship. After being reunited with his body, he will show you to a rowboat, which you will take to stow away on the ghostly ship. Upon reaching the Ferry, you will hear the Ferryman giving a speech to the deceased souls aboard his ship. While the Ferryman will urge you not to, you can light the Well of Fates with the Flame of Souls, breaking open the hold of the Ferry. Upon entry, you will find Jack Sparrow, who can be set free with a key you will take from the Prison Dog.

Saving a Pirate's Life

Upon being set free, Jack Sparrow will attempt to sneak off the ship, but is caught. Shortly after, the Flying Dutchman will emerge from the water, and a battle will commence.


There are 5 journals scattered throughout Sailor's Grave. However, there are a second set of 5 journals in a secret area within the second half of the map.

Cursed Captain's Journals

The Haul of a Lifetime​

(On a table on the top deck of the tavern, Sailor's Grave)

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The Haul of a Lifetime, by the Cursed Captain
After years of scrapin’ by with barely two coins to rub together, we’ve finally struck it rich! Me crew an’ I sailin’ full speed with a hold full of glorious treasure.
They said this ‘Sea of Thieves’ would be packed with plunder – an’ knock me down with a feather if they weren’t tellin’ the truth. Who knew pirates had it in ’em?
But I best be mindful that haven’ a heaping hoard of plunder and keepin’ said hoard are two very different prospects. What I wouldn’t give for a pirate lair o’ me own…
Until I find the proper place to stash me loot, I’ve ordered me crew t’ head far away from the Outposts. We’ll leave the Sea of Thieves and chart a new course if we have to!
Funny thing, though… All these jewels an’ there’s one I can’t seem t’ put down. I found it in me palm again just now. Best t’ hide it from the crew. Best t’ keep it close…


Off the Edge of the Map

(On a table in the back of the ship in front of the tavern, Sailor's Grave.)

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Off the Edge of the Map, by the Cursed Captain
Ol’ Warty Wilkins has been at sea for longer’n I’ve been alive, and even he swears he’s never seen anythin’ like the storm we sailed through tonight.
The wind must’ve whipped it up out of nowhere! Strange green flashes o’ lightning, an’ great rolls o’ thunder that soundeed almost like words.
We’re past the squall now, though I’ll not be content ’til we’ve cleared this wretched fog so we can sight land at last, an’ get some badly-needed provisions.
Funny thing, though. I’ve not felt hungry fer days, not since the last o’ me hair fell out. Guess there’s no point foolin’ myself any longer. We’ve all heard tell or pirate curses!
Still, so what if that jewel has started t’ change me? If I’m to be turned into a skeleton, then I’ll be the richest skeleton that ever sailed the seven seas! HAH


Dissent in the Ranks

(On a table in the bedroom of the shipwreck to the north of the Cursed Captain's cage, Sailor's Grave.)

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Dissent in the Ranks, by the Cursed Captain
I wanted a pirate lair, an’ now I’m in charge of a whole pirate town! More ships an’ sailors keep smashin’ into the rocks, bringin’ new arrivals and supplies.
It’s that witless Lighthouse Keeper’s fault fer lettin’ the flame go out so often, but I let the pirates stay just so long as they join me ever-growin’ crew.
I heard on ungrateful cur call this town a Sailor’s Grave, but I say that’s a fine name. Why should we return to the land o’ the livin’ an’ risk losin’ me plunder?
Me greedy First Mate wants to move the whole haul into Dead Man’s Grotto to keep it safe, but I’m not lettin’ so much as a coin out of me sight…
So long as we remain, the treasure will be ours and ours alone. An’ if those scurvy dogs don’t want their share, so be it. I’ll take the whole heap for meself!


Strange, Yet Familiar

(On a shelf at the top of the lighthouse, Sailor's Grave.)

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Strange, Yet Familiar, by the Cursed Captain
Just when I thought I was doomed to be bored out o’ me skull by this endless fog, I heard Ol’ Warty cry ‘land ho’, though he didn’t sound happy about it.
There was land looming up ahead, sure enough, though we’d no time to change course before we were onto the rocks, good an’ scuppered.
After explorin’ the grotto, we emerged t’ see yet more ruined ships, an’ a great lighthouse, too! It’s the oddest thing, me crew swears it weren’t there before.
Well, we got her beacon burnin’ bright an’ I appointed one o’ me crew to be the Lighthouse Keeper, so long as that light shines, we’re sure to be rescued.
Until then, I’ve set the crew t’ makin’ us some shelters out o’ these scuttled ships, and maybe even a tavern. Funny how this already feels like home…


Lights Out

(On a shelf in the captain's cabin of the Golden Hare, Sailor's Grave.)

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Lights Out, by the Cursed Captain
Treachery abounds! First me own cabin boy makes off with a box full o’ cursed trinkets, an’ now me crew are plotting to betray me an’ save their own hides!
Someone in these parts has been fillin’ their heads with tales of a Ferryman. Promisin’ that one day he’ll come to take their souls back to the livin’ world.
An’ when that day comes, surely they’ll make off with me precious treasure! Well, I’ll not make it easy for any scurvy wretch that’s plannin’ to jump ship.
If ships can’t make it to town in the dark without scuttlin’ themselves on the rocks, it stands t’ reason there’ll be no Ferry to rescue them neither.
It’s settled then – tonight I’ll be indulgin’ in a little treachery o’ me own! Then we’ll see if Mister Ferryman is still so keen to visit Sailor’s Grave…


Headless Monkey Journals

Somewhere in the Caribbean

(Located at the Headless Monkey's Helm, Sailor's Grave)

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Somewhere in the Caribbean, by Captain Kate Capsize.
Today, with more than a little reluctance, I sold my beautiful glass-bottomed boat.
I could hardly bear to let her go, but she’s too small and too slow for the kind of lengthy sea journey I’ll be embarking on. So it’s bye-bye boat.
I have a pressing need for a galleon, something that will see me through thick and thin as I head out on a journey to find the man who framed me.
Luckily, that same man once chartered my glass-bottomed boat and led me to the location of a particularly spectacular shipwreck.
It’s a shipwreck I intend to salvage, repair, and use to track down the dolt who had me sent to jail in his stead. A dolt named Guybrush Threepwood.


Raising the Mad Monkey

(On the broken mizzenmast in front of the Headless Monkey's Helm, Sailor's Grave.)

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Raising the Mad Monkey, by Captain Kate Capsize.
If I’m to locate Threepwood and teach him a very pointy lesson about having innocent people locked up so you can steal their beverages, I’ll need help.
I knew I’d need the help of the local authorities, but infuriatingly, Governor Marley turned out to have eloped with non-other than Threepwood himself. Yuck!
Fortunately, if there is one thing we’re not lacking in this part of the world, it’s bureaucrats. Governor Phatt was ready and willing to meet with me.
I must confess that it turns my stomach to think of my pieces of eight going to feed that man’s endless gluttony, but I’m willing to do what must be done.
Besides, if what I hear about Threepwood’s honeymoon destination is true, I’ll soon have more than enough treasure in my hold…


A Headless Monkey

(By the broken main mast of the Headless Monkey, Sailor's Grave.)

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A Headless Monkey, by Captain Kate Capsize.
THREEPWOOD! A name I shall take great pleasure in etching into a gravestone with my own dagger for what he did to my new ship’s pride and joy.
I’d quite forgotten that the witless, hopeless, clueless buffoon previously removed the head of the figurehead that gives the Mad Monkey its name!
One day I shall take great pleasure in tying the selfish swindler to what remains of the figurehead and parading him around the port, but until then…
Making do, I have returned from the shipwright with a new nameplate for our ship. Together, my new crew and I shall sail on the Headless Monkey!
That’s a name that a certain Guybrush Threepwood, pirate pretender, and his job-ditching bride Governor Elaine would do well to remember…


Fresh Waters

(On a bookshelf in the Headless Monkey's Captain's Cabin, Sailor's Grave.)

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Fresh Waters, by Captain Kate Capsize.
I have a ship, she has a name. I have a crew, we have our course!
The Sea of Thieves is a legendary pirate paradise, home to some of the most feared marauders to ever sail the seas – or so the stories go.
Naturally, only Threepwood would be arrogant enough to presume he has a place there, let alone treat it as a romantic getaway spot for his honeymoon.
If he’d been sailing alone I’m sure he’d be marooned by now, but while Elaine has seriously bad taste in husbands, she’s a capable pirate.
I have to assume that Threepwood somehow made it to the Sea of Thieves. And that means I must do the same.


A Fateful Pursuit

(On a table in the Headless Monkey's Captain's Cabin, Sailor's Grave.)

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A Fateful Pursuit, by Captain Kate Capsize.
Did Guybrush Threepwood make it to the Sea of Thieves? I may never know for sure. I, on the other hand, never arrived. Also, I think I might be slightly dead.
The Headless Monkey is a wreck once again, already part of the weird pirate town they’ve got going on here. There’ll be no salvaging her this time.
I do still have a ship, though – my little glass-bottomed boat! How can it be here, in this strange not-life full of ghostly voices? Maybe I shouldn’t ask.
My crew are off in the tavern, and I don’t think they’ll be leaving any time soon. They’re at home here in a way that I can never be. I miss the sunlight!
I am going to set sail, find a way back to life and then… Well, let’s see what the seas have in store! I’ve realized revenge isn’t worth living, and certainly not dying, for.


Commendations and Rewards

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Strange ShoresSuccessfully navigate Dead Man's Grotto.n/a
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Tales of the DeadRescue the Cursed Captain.n/a
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Waiting for EternitySummon the Ferry of the Damned to Sailor's Grave.n/a
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Raising the DeadLearn what happens to pirates who betray other pirates.n/a
Treasure for the Dead emblem.png
Treasure for the DeadReturn a treasure to its 'rightful' owner.n/a
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A Powerful ThirstHelp quench the thirst of one who cannot help themselves.n/a
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Ship of ThievesFind a way to open the door of a locked ship.n/a
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Secret of the GraveDiscover the secret of Sailor's Grave.n/a
The Prisoner emblem.png
The PrisonerRelease the Ferryman's prisoner.n/a
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A Pirate's LifeComplete 'A Pirate's Life'.Lock icon.png Unlocks the Cursed Captain's Hat in the Clothing Chest.
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Tales of the DamnedDiscover the Cursed Captain's Journals in Sailor's Grave.n/a
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The Crew of the Headless MonkeyDiscover the Journals of the Headless Monkey's Captain.n/a
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Mist and MemoryLegendary Commendation: Complete all commendations for 'A Pirate's Life'.Lock icon.png Unlocks the Cursed Captain's Sails in the Ship Customization Chest.


  • Some of the ghostly voices originated from the Disneyland ride, Pirates of the Caribbean.
  • The Cursed Captain can say a variety of lines when the player performs some actions, which include taking him to various locations in Sailor's Grave, performing actions, and even reacting to the secrets of Sailor's Grave.
  • The Headless Monkey shipwreck and the lore in its journals are an Easter egg to the Monkey Island series.

Patch history

  • 2.9.0 (October 19, 2023)
    • Players can now consistently pick up the Cursed Captain’s skull after placing it at Poor Dougie’s grave.
    • Players should no longer be able to become stuck behind the shipwreck hull after opening the first gate.
  • 2.7.1 (December 15, 2022)
    • ‘A Pirate's Life’ – The torches within Dead Man's Grotto will now light correctly when performing the required actions.
  • 2.5.0 (March 10, 2022)
    • It is now impossible to bypass the sidequest to reach the locked ship and the rewards inside.
  • 2.2.1 (August 17, 2021)
    • The Ship's Map Table should now be hidden after joining a Tale already in progress or rejoining a session.
    • When using a Wraith Statue to return to the correct location after using a checkpoint, players should now be facing the intended direction on arrival.
    • If a crew’s ship has been sunk within the Sea of the Damned, the Wraith Statue will still allow players to return by spawning a new ship for them. This ensures that players can always cancel the Tale and return to the Sea of Thieves.
    • When lighting a lantern that requires the Flame of Souls, the prompt should now say "Requires Flame of Souls to light".
    • In Dead Man's Grotto, thick fog banks now visually cover the areas that players are unable to reach.
    • The ghosts within Dead Man’s Grotto now fade in sooner so there is little or no delay, ensuring players do not miss them.
    • The ghostly tankards should now correctly fade in alongside the ghosts in the broken lever room.
    • The music now fades in and out naturally or starts again after passing over the first bridge to Sailor's Grave then immediately walking back across.
    • While exploring Sailor's Grave, players should no longer be able to navigate around the rocks to access the treasure-laden ship before it is opened.
    • Players far away from the lighthouse should now be able to see the movement of its light.
    • Players should no longer be able to use a Rowboat to access the mysterious wreck before it is opened.
    • Players should no longer be able to cross the bridge into Sailor's Grave without using the beacon to raise the bridge mechanism.
    • Upon locating the Cursed Captain's Ship, players should no longer be able to make their way up the rocks to access the ship before it has been opened.
    • There is no longer a pop sound before the Cursed Captain's crew can be seen on the deck of the Cursed Captain's ship.
    • The Cursed Captain's subtitles are no longer missing when the player collects the Cabin Key.
    • After digging up Poor Dougie's Chest, the prompt to use a key on the chest now correctly spells Dougie's name.
    • The collision on the chandelier in the Sailor's Grave tavern now works as intended.
    • Ghost pirates now populate the tavern in Sailor's Grave when the Tale is started from a checkpoint.
    • The tavern ghosts' gunfire VFX and audio no longer continue playing in the Sailor's Grave tavern after the ghosts have faded following the Ferry of the Damned's arrival.
    • Players should no longer respawn on the Ferry of the Damned after dying before they have boarded.
    • Crews reaching the Ferry of the Damned can no longer interrupt the Ferryman's speech and block progress by interacting with the Well of Fates.
    • When interacting with the Prison Dog on the Ferry of the Damned, the prompt now correctly says “Take Brig Key”.
    • Players should now be able to pick up the keys after putting them on barrels near Captain Jack Sparrow's cell.
    • Audio effects now play when the Ferryman throws his sword and Jack picks it up.
    • The prompt for closing the sarcophagi now says “Close” rather than “Open”.
    • If the tunnel migration fails after the Tale is finished, subtitles for Jack Sparrow's dialogue no longer appear.
  • 2.2.0 (June 22, 2021)
    • Introduced.