Guide to A Pirate’s Life Tall Tale

Journey to the Sea of the Damned

Published in

Golden Sands Blogpost

11 min readJun 22, 2021

A strange Castaway warns of danger, both to the Sea of Thieves and the pirate’s life itself…

Tall Tales are story-based voyages in the Sea of Thieves that you can experience alone or with your crew in Sea of Thieves. They tell a narrative and involve solving puzzles, using unique mechanics, and overcoming perils.

The A Pirate’s Life Tall Tale is the first part of the A Pirate’s Life saga, which consists of FIVE parts depicting the epic adventures of Captain Jack Sparrow from Disney’s Pirates of the Caribbean franchise, finally crossing over into the world of Sea of Thieves!

This guide walks through the A Pirate’s Life Tall Tale, detailing what to expect at each step, how to solve the expansive side quests, as well as where to find those pesky hidden Journals. This guide may contain spoilers, so read at your own risk.

Rewards for A Pirate’s Life

Complete the A Pirate’s Life Tale for the first time to unlock the Cursed Captain’s Hat cosmetic.
Complete every “side quest” (more on these below) along with reading every Hidden Journal on the Tale, and you’ll unlock the Cursed Captain’s Sails
Every time you complete the Tale, you also pocket 8,000 Gold

Overview of “A Pirate’s Life”

The first Tale in the “A Pirate’s Life” saga follows this basic structure:

Sail through a portal to the island in the Sea of the Damned where the Tale takes place
Arrive in “Dead Man’s Grotto”, a linear dungeon to progress through to reach…
Sailor’s Grave- a ghostly pirate town that is a wide open area to explore, filled with a lengthy side quest, and 10 hidden journals you must read to complete all the commendations
If you want to skip the side quests and journal-searching, you can progress straight through the story, where’ll you leave the Sea of The Damned on one last epic encounter…

Note: We will first walk through the “Core Story”, segmenting off the Side Quest and Journal Locations for lower down in the Guide if you wish to avoid them as spoilers. While walking through the Core Story, we will keep descriptions of your challenges vague while pointing pirates in the right direction, so as not to spoil the Story, Lore, or Action.

The Side Quest and Journal Locations will feature heavy spoilers, so read at your own risk!

Beginning the Tall Tale

The Tall Tale can be started from any Outpost in the game, which is where you’ll spawn if you load in to Play from the Main Menu in “Adventure Mode”. Simply walk out to the beach to find the mysterious Castaway huddled around a green campfire.

If you choose to load in to Play from the Main Menu using the “A Pirate’s Life Mode”, you will still enter the Sea of Thieves shared world and spawn in at an outpost, though you’ll spawn directly at the Castaway’s Camp and skip any other pop ups that may distract you when first loading into a session.

In either case, approach the wall backdrop behind the Castaway, and find the model ship next to a tattered old book. You’ll see the pop-up menu for “A Pirate’s Life” and the option to Vote for Tall Tale. Doing so with your crew will prompt the Castaway to deliver introductory dialogue, and now you’re on your way!

Reaching the Sea of the Damned

Once The Castaway is finished, return to your boat parked at the outpost’s dock, and get ready to sail! As described in the narration, a portal will open nearby at sea, so look around for the giant rock formation with green portal effects and swirling clouds above. You’ve gotta sail into there. (NOTE: whenever sailing into such a portal, you will drop any treasure you’ve gathered on your ship before hand!)

Once through the portal, you’ll enter a loading zone called the Tunnels of the Damned. You cannot steer the ship or jump off your boat, you are simply along for the short ride, watching and listening to the ghostly apparitions, until eventually you exit another portal- now in the Sea of the Damned.

Once you resume control of your ship, you’ll be headed for an island straight on. Make sure to come to a safe stop, and then you can head inland. There’s only one cave path to follow, so head through and enter Dead Man’s Grotto…

Navigating Dead Man’s Grotto

Dead Man’s Grotto is a fairly straightforward linear cave that only requires a few simple puzzles along the way in order to progress. There are no side quests or Journals to find in Dead Man’s Grotto, so enjoy the ride.

In each “room”, you’ll find your progress gated behind some simple puzzle. Try scanning around nearby for clues and things you can interact with in order to get the next doorway to open up, like lanterns, levers, pulleys, etc. You’ll never need to back track behind a doorway you’ve already opened.

Simply follow the path forward, and every time a gate stops your forward progress, look around the immediate area for things to interact with. Dead Man’s Grotto is mostly a cinematic ride, but once completed, you’ll arrive in the much more open Sailor’s Grave…

Sailor’s Grave: Finding the Cursed Captain

Now you find yourself in Sailor’s Grave, a much more wide open area to explore.

NOTE: This area has ALL the Side Quests and Hidden Journals to discover, if you are going for total completion. We discuss each of these SEPARATELY at the bottom of this guide, so you can avoid spoilers. We will now detail the CORE STORY challenge needed to progress, and save the side content for down below!

Once you find your way into the area below, you’ll quickly hear the call of a Cursed Captain, begging for your help to retrieve his skull from a hanging cage. Listen to the Captain’s dialogue for hints on how to get up there. It will involve climbing across several structures, diving through a shipwreck, and raising pulleys to eventually reach the top. Try interacting with the cage and see how you can make it fall! Once dropped, approach the Captain below. He explains where to find the key to his cage, which his crew is keeping in a tavern nearby. Once you’ve found his crew, look around for things to interact with until you finally spot the key, allowing you to save the Captain from his prison.

Once released, you can carry the Cursed Captain’s skull with you all throughout the Tale, and he’ll comment on things you bring him near to. You’ll need to take him with you to make it through the rest of the Tale!

The Lighthouse and Beyond:

Once you pick up the Cursed Captain’s skull, he’ll immediately suggest that you head to the old Lighthouse, which is the next step on the Core Story if you aren’t interested in exploring the Side Quests and Hidden Journals (read on them at the bottom of this guide).

When you approach the Lighthouse while carrying the Captain’s Skull, it will prompt the bridge to raise, allowing you to ascend the lighthouse where you’ll find numerous things to interact with. The Captain’s dialogue helps to understand what you’ll need to do here, and once you’ve figured it out, the Captain will find a Key that he puts conveniently between his teeth, instructing you to then head to his Ship farther up the beach (marked by sails with crossed swords).

If you enter the Captain’s Ship and progress through to his Captain’s Cabin, you will reach a point of no return, where the side quests will no longer be completable once you’ve reached this checkpoint. If you plan to explore Sailor’s Grave more, don’t enter the Captain’s Ship!

The Final Voyage

Once you’ve made it through the Cursed Captain’s ship to the exit out the back of the Captain’s Quarters, take the rowboat for a spin and dock it to the back of the Ferry of the Damned. Now it’s time to take a ride.

After a short dialogue, you can interact with the Flame of Fates in the center of the deck to get the action started. Enter the deck of the ship, and take note that this first room has fruit and cannonball supplies. Through the next couple rooms, look for things to interact with until you manage to open the door and progress. Once you enter the lower hull, the task is clear through dialogue what needs to be done.

When ready, return to the top deck where you’ll face a battle involving numerous threats, making use of your cannons as well as your hand to hand combat. When you complete this battle and finish all of the cutscenes, exit through the Captain’s Door of the Ferry of the Damned, and the Tall Tale will be complete. Congratulations on beginning your journey through A Pirate’s Life! For our Guide to the Second Part of the story, “The Sunken Pearl”, click here.

Yarrrr, here, there be Spoilers…

In the sections below, we’ll detail how to solve the elaborate Side Quest of A Pirate’s Life, and then at the very bottom of the Guide, detail the locations of all 10 Hidden Journals. If you want to find this content on your own, stop reading here!

The Side Quest

Sailor’s Grave has an elaborate Side Quest with multiple steps involved to solve everything. This is required in order to complete all commendations and unlock the best cosmetic rewards.

Step 1: The Map in the Tavern

Find your way to the top floor of the Last Stand Tavern. There, after lighting a candle, a Map is revealed detailed the first clue of the Side Quest. Find the location marked by an X on the map, and once you’re in the right spot, you’ll discover that the treasure here has already been taken! But an obvious clue should lead you to the other side of Sailor’s Grave, where you should dig to discover a hidden surprise. A pirate here has a key to a chest, but you’ll need to explore elsewhere to find it…

Step 2: The Map in the Pirate’s Bed

When you first enter the wider Sailor’s Grave area, you passed through a large ship that was broken in two halves. Find your way inside the interior of the front half, and a Pirate is studying a map in bed using their magnifying glass. You’ll need to get some “light” on the subject, so explore around this area a bit until the map reveals its clues. Once you know where to go, you’ll be able to find the chest that goes to the key in Step 1. Inside is a medallion, which you’ll need soon.

Step 3: The Chess Match

In the back half of the same wrecked ship, find your way inside the rear to discover some skeletons playing Chess. Lighting their candle will bring them to life, but they won’t interact with you until they get a special drink recipe. Leave the medallion here, along with the Cursed Captain’s skull, as they’ll both be needed. But first, we gotta go get that grog…

Earlier in the Tale you used pullies to reach the cage of the Cursed Captain, follow this path again and just behind the peak where the Captain’s cage hanged, there’s a small cell containing the drink we need. There appears to be no way to open the door from the outside… but if you look closely, you’ll find a hidden side entrance instead.

Bring the drink recipe, the medallion, and the Cursed Captain’s skull all to the Chess match. First, give the skeleton the drink, then buy in to the game with the medallion, finally, perch the Captain’s skull onto the skelly, and you’ll finally receive a key.

Step 4: Unlock the Locked Ship

Once again, return to the pulley area from before, atop which you’ll find a locked door of a ship with treasure inside. On the deck of this ship, you can adjust the sails, which are obstructing some kind of beacon/brazier. How can we light this beacon? Think hard, because it’s the final challenge to reaching the end of the Side Quest…

Step 5: Cross the Final Bridge

Back at the bottom of the hill when you first enter Sailor’s Grave, immediately to the right is a bridge that is now accessible. On the other side is a tremendous Easter Egg, along with 5 Hidden Journals to read for commendations (more on them below).

Hidden Journals

The Hidden Journals in A Pirate’s Life are split into two categories. The Cursed Captain’s journals (5) are all hidden throughout Sailor’s Grave, including 1 in his Captain’s Cabin near the end of the Tale. The Journals of the Headless Monkey’s Captain (5) are all hidden across the Easter Egg Bridge you can only cross after solving the Tale’s elaborate Side Quest. Here are the Journal locations: