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When two pirate icons cross paths, something magical happens. Sea of Thieves’ "Legend of Monkey Island" Tall Tales aren’t just fan service—they’re a full-fledged fusion of witty storytelling, layered puzzles, and nostalgic flair. Blending Rare's open-sea chaos with the razor-sharp humor of Guybrush Threepwood’s world, this trilogy of quests reimagines the classic Monkey Island experience for a new generation of pirates.

This guide will walk you through each of the three chapters, from your first step on Mêlée Island to your final clash with the undead menace LeChuck, ensuring you unlock every reward, find every hidden journal, and understand every challenge along the way.

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Getting Started: How to Begin the Monkey Island Quests

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To launch these Tall Tales, visit any Outpost and look for the wrecked vessel marked "Capsize Charters," where Captain Kate Capsize offers passage into the Sea of the Damned. Interact with the Tall Tale book aboard the ship to begin your journey.

Each chapter unlocks in sequence, so you’ll need to complete the first to access the next. While sailing solo is possible, bringing along a trusty crew can help split up the work and uncover secrets faster.

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Chapter One: The Journey to Mêlée Island

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You arrive at a ghostly version of Mêlée Island—a near-perfect echo of the original game’s setting. With Guybrush nowhere to be found, it’s up to you to set things right.

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Primary Objectives

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Collect Pieces o' Eight: Coins are hidden everywhere. Search thoroughly—behind barrels, atop beams, even inside furniture. You’ll need these to purchase essential items like the Chef’s Uniform and the History Book.

• Interact with Island Characters: Locals like Murray the talking skull and Spiffy the dog offer essential interactions. Talk to everyone, and remember to sit at the Scumm Bar for a commendation.
• Fix the Town Clock: Completing this side quest advances the story and opens new areas.
• Rescue Otis: Find a way to open his cell—it’s part of a commendation and continues the narrative.
• Face the Ghost Pirates: Use Root Beer Bottles as weapons. You’ll need them to deal with waves of undead that threaten the town.

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Chapter Two: The Quest for Guybrush

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Guybrush is locked in a dream-like trance, and only by completing three legendary pirate trials can you bring him back.

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Legendary Trials

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• Insult Sword Fighting: Combat here is verbal. Match the correct comeback to your opponent’s insult to win. It’s all about memory and wit.
• Circus Obstacle Course: Race through a timed gauntlet filled with collapsing platforms and trick traps. Precision counts more than speed.
• The Beast’s Lullaby: Use the correct musical shanty to soothe a monstrous creature. Contextual audio clues help guide you to the right tune.

Each trial not only progresses the story but unlocks commendations for those aiming to collect every reward.

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Chapter Three: The Lair of LeChuck

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Now you’re deep in enemy territory. The atmosphere shifts—crimson skies, shadowy caverns, and the looming presence of LeChuck set the tone for the final chapter.

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Key Objectives

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• Collect Golden Monkey Idols: Solve environmental puzzles and use visual cues to find and correctly place these idols.
• Read LeChuck’s Journals: These journals reveal not just lore, but clues essential for completing puzzles.
• Solve the Light Beam Puzzle: Redirect light beams using mirrors to unlock a cage and move deeper into LeChuck’s lair.
• Final Confrontation: It all builds to this. Bring your best aim, a few Root Beer Bottles, and quick reflexes for the last face-off.

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Commendations Breakdown

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Each Tall Tale offers a suite of commendations tied to exploration, puzzle-solving, and interaction. Completionists should focus on the following:

For Chapter One: Focus on collecting coins, unlocking the town clock, rescuing Otis, and speaking with every character. This chapter unlocks the Chef’s Uniform, the History Book, and multiple commendations.

For Chapter Two: Complete all three legendary trials—Insult Sword Fighting, the Circus Obstacle Course, and the Beast’s Lullaby. Also, take time to visit each memoir spot scattered through the environment. Your reward includes the Circus Superstar Costume and related commendations.

For Chapter Three: Locate all three golden monkey idols, solve the beam light puzzle, read every one of LeChuck’s journals, and make it to the final showdown. You’ll unlock the Burning Blade Cutlass, the Monkey Island Shanty, and unique ship decorations.

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Ready to Set Sail?

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You can’t chart this course without the game in hand. Grab your Sea of Thieves Xbox One/Windows CD Key from ​ RoyalCDKeys ​ and get ready to sail into one of the most entertaining adventures Sea of Thieves has ever offered. The Tall Tales are available to all players, but having the right crew and the right key is how legends begin.

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Final Thought

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The Legend of Monkey Island quests strike a rare balance—they entertain, challenge, and reward those who take their time to explore. It’s a love letter to pirate storytelling, and a reminder that sometimes the best treasure is the tale itself.

Discover more in our recent article: Top Mods to Enhance Baldur's Gate 3 Gameplay ​