Longtime pirates and newcomers alike continue to set sail for the wild crossover between Rare’s multiplayer sandbox and Disney’s Pirates of the Caribbean franchise. Since its release in 2021, Sea of Thieves: A Pirate’s Life has remained one of the most celebrated expansions in the game’s history, and even in 2026, the tall tales starring a digital (and delightfully tipsy) Jack Sparrow are still a rite of passage for any crew. Among the many tasks woven into this cinematic adventure, locating all five Headless Monkey Captain journals stands out as a mini treasure hunt that tests a pirate’s eye for detail. The payoff is well worth it, rewarding players with progress toward commendations and a special surprise that the community has long been asking for.

Before anyone can step foot onto the doomed vessel, a fair amount of nautical legwork must be done. The wreck of the Headless Monkey is sealed away behind a rickety bridge in the spooky Sailor’s Grave. To lower that bridge, players need to lend a hand to the eternally unfortunate Poor Dougie and track down Captain Bones’ Special Recipe. This whole sequence not only unlocks the next chapter of the tale but also topples a chain of commendations along the way, making the effort doubly rewarding. Once that bridge creaks open and the ghostly silhouette of the Headless Monkey comes into view, the real search can begin.

Here is a step-by-step breakdown of where to find every journal onboard the wreck. Keep a sharp eye out for skeletons, lanterns, and scattered ship parts—they’re the best landmarks for navigation.

📜 Journal 1 – “Somewhere in the Caribbean”

The moment you clamber onto the Headless Monkey shipwreck, head for the wheel. Right there, sprawled beside a skeletal crewmate, lies the first journal. Don’t leave without grabbing the cabin key from that same skeleton—it’s vital for the later journals.

📜 Journal 2 – “Raising the Mad Monkey”

Turn around from the wheel and you’ll spot it immediately, tucked snugly against the ship’s mast. It’s hard to miss once you know where to look.

📜 Journal 3 – “A Headless Monkey”

Eagle-eyed pirates might have caught a glimpse of this one while boarding. If not, make your way amidships. Underneath a broken mast, right beside a glowing lantern, is the third journal. The combination of light and shadow here makes it one of the more atmospheric finds.

📜 Journal 4 – “A Fateful Pursuit”

Now, remember that cabin key you picked up earlier? Time to use it. The cabin door sits on the far side of the wreck. Inside, a small table holds the fourth journal, neatly placed between an old map and a flickering lantern.

📜 Journal 5 – “Fresh Waters”

You’re almost done. Just a couple of meters from the cabin table, inspect the nearby bookshelf. The final journal rests there, waiting for a collector’s touch.

Collecting all five journals is satisfying on its own, but the true treasure comes from tying together every tall tale in the crossover. In true Rare fashion, the developer has hidden a particularly coveted reward for pirates who complete the entire A Pirate’s Life saga. While we won’t spoil it here, fans have consistently dubbed it one of the most requested features ever introduced to the game. It’s the kind of unlockable that makes revisiting these adventures—even years later—an absolute delight.

The Headless Monkey quest also acts as a clever piece of worldbuilding, weaving together the slapstick humor of Jack Sparrow with the eerie atmosphere of the Sea of Thieves. Every journal entry adds a little more flavor to the cursed ship’s backstory, giving players a reason to slow down and read amidst the chaos of naval combat and skeleton raids.

For those attempting the hunt for the first time in 2026, a few tips can make the voyage smoother. Team up with a full crew to divide the search, keep your lanterns raised in the darker corners of the wreck, and always check interactive maps shared by the community if you get turned around. The Headless Monkey is not a gigantic ship, so the journals are never far apart, but the dim lighting and twisted debris can still play tricks on even veteran sailors.

Sea of Thieves: A Pirate’s Life remains available on PC, Xbox One, and Xbox Series X/S. Whether you are reliving the adventure or discovering it for the first time, the hunt for the Headless Monkey journals is a timeless piece of pirate storytelling that continues to charm players across the globe. 🌊🏴‍☠️