Preparing for Return to Monkey Island: How to be the Mightiest Pirate in The Secret of Monkey Island

We’re all very excited for Return to Monkey Island here at Expansive.

It still feels like a fever dream that later this year we’ll be playing a brand new Monkey Island game from Ron Gilbert and Dave Grossman. Let alone one that continues the story from LeChuck’s Revenge!

Of course, we’re well aware that some people may be looking to revisit the originals before then and are finding themselves a little bit stuck.

Never fear, we’ve put together some handy walkthroughs for some of the game’s toughest puzzles in Part One which might just arr’lp!

Part One: The Three Trials


How to find the Swordmaster

One of the Three Trials is to defeat the Swordmaster, but first you need to figure out where she is! Fortunately, the trusty shopkeeper in Melee Island knows exactly where to find Carla. Mostly because he’s a little bit obsessed with her.

Just ask him, and he’ll leave the shop unattended to go visit. This is your cue to follow him closely through town and into the forest clearing. Eventually he’ll take you right there so you can sneak by and confront the Swordmaster for an epic showdown! Although…you should probably have a Sword and know how to use it first!

Where can I get a Sword and the right training?

Fortunately, the Storekeeper also has a good enough Sword you can buy (along with a Shovel, but we’ll worry about that later) As for how to pay, you can get some money by helping the Fettucini Brothers at the circus.

Before you do, go back to the Scumm Bar and head to the back next to the Three Very Important Looking Pirates. Wait for the Chef to walk out, sneak into the kitchen and pick up the pot. While you’re there, get the fish from the seagull on the jetty by walking onto the bottom right plank three times. When it’s launched in the air, snatch it from underneath its beak. Now dip the fish in the pot of stew and pull it back out again (You’ll need this later)

Once you’re done, you can head to the Fettucinis and when they try to fire you out of the cannon, put the pot on your head and you’ll be rich beyond your wildest dreams. Well, rich enough to buy the sword back in town, at least.

But just because you have a sword, doesn’t mean you’re ready for battle. Head back to the map and across to the bridge where the Troll is asking for a toll. Give him your stewed fish and pass through to a house where you’ll meet a Sword Trainer. Convince him you have what it takes and you’ve got the money to prove it and he’ll teach you the basics of Insult Sword Fighting.

Now can I beat her?

Not quite. Now you need to start tangling with the random pirates roaming around the map. Just wait for one to bump into you and start challenging them.

You’ll need to beat at least three of them and keep fighting your way through them until you’ve learned all the Insults and Responses. There’s 16 altogether, so it’s probably best not to go back to the Swordmaster as soon as they say so.

Here’s all of the insults along with the right comeback.

Insult Comeback
You fight like a dairy Farmer! How appropriate. You fight like a cow!
This is the END for you, you gutter crawling cur! And I’ve got a little TIP for you, get the POINT?
I’ve spoken with apes more polite than you! I’m glad to hear you attended your family reunion!
Soon you’ll be wearing my sword like a shish kebab! First you’d better stop waving it like a feather duster.
People fall at my feet when they see me coming! Even BEFORE they smell your breath?
I’m not going to take your insolence sitting down! Your hemorrhoids are flaring up again eh?
I once owned a dog that was smarter than you. He must have taught you everything you know.
Nobody’s ever drawn blood from me and nobody ever will. You run THAT fast?
Have you stopped wearing diapers yet? Why? Did you want to borrow one?
There are no words for how disgusting you are. Yes, there are. You just never learned them.
You make me want to puke. You make me think somebody already did.
My handkerchief will wipe up your blood! So you got that job as janitor, after all.
I got this scar on my face during a mighty struggle! I hope now you’ve learned to stop picking your nose.
I’ve heard you are a contemptible sneak. Too bad no one’s ever heard of YOU at all.
You’re no match for my brains, you poor fool. I’d be in real trouble if you ever used them.
You have the manners of a beggar. I wanted to make sure you’d feel comfortable with me.

Now when you’re ready you can head back to the Swordmaster. But be warned, Carla plays by her own rules and actually has her own insults. This can definitely get confusing and throw you off, but don’t worry you’ve got everything you need, just look out for cue words and you’ll be fine.

Or, you can just check out the handy guide below…

Insult Comeback
Now I know what filth and stupidity really are. I’m glad to hear you attended your family reunion.
Every word you say to me is stupid. I wanted to make sure you’d feel comfortable with me.
I’ve got a long, sharp lesson for you to learn today. And I’ve got a little TIP for you. Get the POINT?
I will milk every drop of blood from your body! How appropriate, you fight like a cow!
I’ve got the courage and skill of a master swordsman.
  1. I’d be in real trouble if you ever used them.
  2. He must have taught you everything you know.
My tongue is sharper than any sword. First, you’d better stop waving it like a feather-duster.
My name is feared in every dirty corner of this island! 1. So you got that job as a janitor, after all.2. Too bad no one’s ever heard of YOU at all.
My wisest enemies run away at the first sight of me! Even BEFORE they smell your breath?
Only once have I met such a coward! 1. He must have taught you everything you know.2. I’m glad to hear you attended your family reunion.
If your brother’s like you, better to marry a pig. You make me think somebody already did.
No one will ever catch ME fighting as badly as you do. You run THAT fast?
My last fight ended with my hands covered with blood. 1. I hope now you’ve learned to stop picking your nose.2. Your hemorrhoids are flaring up again, eh?
I hope you have a boat ready for a quick escape. Why, did you want to borrow one?
My sword is famous all over the Caribbean! Too bad no one’s ever heard of YOU at all.
You are a pain in the backside, sir! Your hemorrhoids are flaring up again, eh?
I usually see people like you passed-out on tavern floors. 1. Even BEFORE they smell your breath?2. I’m glad to hear you attended your family reunion.
There are no clever moves that can help you now. Yes, there are. You just never learned them.

Congratulations, you’ve finished one of the Three Trials and got the T-Shirt to prove it!

How to find the Treasure

This is often the Trial that catches people out and for good reason. The steps to get there can be quite tricky but we’ve got you covered.

Your first point of call is the dodgy-looking pirate on Melee Island street corner who’s selling maps to treasure (Yes, these are actually genuine) – Using the Pieces of Eight you got earlier, you now know how to find the X-Marked Spot.

Next up, go back to the Storekeeper and pick up the Shovel, you’re going to need it!

Head to the map and go to the Fork. This is where the steps indicated on the map come into play. First, though, go to one of the two exits at the top of the screen and pick up a yellow flower petal you see there. That’ll come in useful for the other Trial!

Now, then, time to follow the steps. Go…

  • Left
  • Right
  • Left
  • Right
  • Up
  • Right
  • Left
  • Up

Once you enter the clearing, head right and you should see a bulletin board and a large X on the ground. Take the shovel to it and you’ll get the treasure.

Or should I say another T-Shirt…

How to find the Governor’s Idol

The final Trial is all about Thievery and the Governor’s Mansion is your target. Remember that Yellow Flower you picked up on the way to the Treasure? It’s about to become very useful.

First head to the Scumm Bar and if you haven’t already, pick up the hunk of meat from the Kitchen (once again waiting for the Chef to leave) and dip it in the stew to get some stewed meat. Now use the Yellow Flower with the meat and head back outside. Go past the Storekeepers shop and the alleyway and go out underneath the archway towards the Governor’s Mansion.

Before you can go inside, you’ll need to do something about the Poodles. The drugged meat will send them right off to sleep but don’t worry, they are only sleeping.

Once inside, the game will kind of play itself for a little while once you enter the back room. You can interact at various stages, but this is essentially an extended cutscene as Sheriff Shinetop gets involved, trying to stop you. Once you lock him inside, you realise you need something else to get the Idol. Back outside we go.

You need to chat to Otis in the Jail Cell. Problem is, his breath is so bad you can’t even face him. The Storekeeper has just the thing, a roll of breath mints which you can buy from him by just asking. Give Otis one and you can have finally have a conversation. He wants to do something about the rat in the other cell, so give him the Gopher Repellant you just picked up from the Governor’s Mansion and he’ll return the favour with some Carrot Cake. Aww, how nice.

If only he’d have eaten it / opened it up, as he would have found a file to help him escape. We can help him another time, but for right now we need this to complete the Trials. Head back to the Governor’s Mansion, dive back in through the hole in the wall and another cutscene begins!

Eventually, you’ll get the Idol and be confronted by the Governor who seems more than happy for you to take it. Congratulations! Well, kinda…

The Sheriff is not happy, so he captures you and throws you in the water along with the Idol. There’s something dodgy about him. You could leave Guybrush under water for ten minutes and let him die, or you could pick up the idol you’re tied to and climb back up, picking your sword up along the way.

Now it’s time for congratulations! Maybe…

Getting a band together

Guybrush is kind of a pirate now. Good timing, as the Governor’s been kidnapped. To get her back, he’ll need a mighty crew to pull off a mighty rescue mission. Fortunately, you’ve met some solid characters on Melee Island who could help out. Including one guy who’s in a bit of a jam.Time to bust him out.

Once the Ghost Ship has gone and the cutscene has ended, head to the Scumm Bar and pick up all the tankards you can see. In the back, the Chef is upset so the Kitchen is all yours.

Use one tankard on the grog barrel in the back and move outside as quickly as you can, you’re going to need to be fast. Keep an eye on the tankard in your inventory and as soon as it starts to melt, use the tankard on another empty one to transfer the grog. You’ll need to keep doing this until you get back to Otis who’s still stuck in jail. If you’ve done it right, you should be able to pour the grog from a tankard on the cell’s lock and Otis will be free. He will be overjoyed and seem to run off, but he owes you one and will remember his debts.

Next up is the Swordmaster. Humbled by you earlier on, Carla seems to be lacking a bit of purpose and upon hearing the Governor is kidnapped, she’s more than happy to join your crew. Nice!

Last up is Meathook, who resides on the island at the top of the map. If you haven’t visited him up to now, you’ll first need to go back to the Village and past where you met the dodgy map dealer and the three would-be pirates, there’s a door you can enter before going under the archway that will take you to a voodoo priestess. Inside, you’ll find a Rubber Pulley Chicken on the table, grab it and head back to Meathook’s.

Use the Rubber Chicken on the cable wire after climbing the ladder and you’ll sail over to his house and can walk right in. When you tell Meathook the Governor has been kidnapped, he says he’ll join your crew but only if you do something he couldn’t…face his fear. Walk deeper into the house, touch the murderous winged devil and Meathook will be all yours to command.

Now we have a crew.

But what about a ship?

Yeah, that would be helpful, wouldn’t it? Time for a trip to Stan’s Previously Owned Vessels. A man you can trust as far as you can throw, but you don’t really have much choice.

Listen to his rantings and ravings about the different ships on offer, you need to go for the ship that costs the lowest amount of money, only to discover you still can’t afford it. So when the option comes up, you should mention you want a ship on credit. At this point, Stan will direct you to the Storekeeper of Melee Island who might be able to help.

Head on over there and when you ask the Storekeeper about credit, say you have a job. Then pay very close to how he opens the safe. This is usually random so you’ll need to remember the combination. When he can’t fill out the credit for you, ask the Storekeeper to find the Swordmaster again for you, then when he’s gone open the safe using the combination by pulling and pushing the lever, take the note and leave.

Go back to Stans, check out the cheap ship again and when it comes to Extras, say you can live without all five of them to get the cost down even further. Then ask Stan what he thinks its worth, then you can make him an offer for 5,000 Pieces of Eight. Stan will eventually agree, take the credit note from you, and you have yourself a ship! Woohoo.

Return to the Village and the Dock and prepare for Part II of The Secret of Monkey Island.

That’ll do it for Part 1 of The Secret of Monkey Island. We’ll be back for the remaining Parts at a later date, but in the meantime let us know if you have any questions/ if you’re stuck in a particular area.

The countdown to Return to Monkey Island is on!

About the author

Sally Willington

Sally is relatively new to gaming since a newfound addiction to Nintendo Switch. Now they just can't stop playing, anything and everything. Sally especially loves a good RPG and thinks that Yuna may just be one of her favourite characters ever.
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