If you're doing this as a fresh master, you will want another person with you. A Grand Master can solo this quest
Rewards
32,575,000 experience
Shinguards
Walkthrough
Go to Lynith Beach from the world map
Head to Lynith Beach South and board the ship at 44,19
Go down the stairs to 19,17 and enter Pirate Hall 1
Go around to get into the Main Hall
To start, you will need to speak to any of the pirates in the side rooms
Speaking to them without a pirate item on (overarmor, helmet) will have them throw you into the brig. We want this at this time.
Hunt the pirates in the brig. You are going to need one of each of the following items. If you're bringing a party, each of you will need one:
Red Pirate Bandana
Black Pirate Bandana
M Pirate Shirt
M Pirate Garb (this felt like the lowest drop rate item)
Once you have all of the items, head back to the Main Hall and equip a pirate item (overarmor or helmet)
From the main hall, go to 32,18
Speak to Savage Sable
Select "Are you okay?"
Select "That's not right."
Select "I sure can Sable."
Speak to Sable again
Select "I have your Red Pirate Bandana."
If you don't have the bandana in your inventory when you select this option, you'll be thrown back into the brig
You are rewarded with 75,000 experience
Leave the room and head to the room at 16,3
Speak to Salty Sam
Select "Are you looking for something?"
Select "Would you like me to get you one?"
Select "Please stop jumping, I will be back with it."
Speak to Salty Sam again
Select "I got your Black Pirate Bandana."
If you don't have the bandana in your inventory when you select this option, you'll be thrown back into the brig
You are rewarded with 250,000 experience
Leave the room and head to the room at 23,3
Speak to Jolly Roger
Select "Could I get you something?"
Select "Ah, no problem. I can find one."
Speak to Jolly Roger again
Select "I found a Male Pirate Shirt."
If you don't have the shirt in your inventory when you select this option, you'll be thrown back into the brig
You are rewarded with 750,000 experience
Leave the Main Hall north at 1,11 and exit back to the Pirate Ship Deck
Head up the stairs and enter the Navigation Room at 11,15
Speak to Captain Wolfgang
Select "What else do you need Captain?"
Select "Would you like me to get you one?"
Select "Yes Captain, be back soon."
Speak to Captain Wolfgang again
Select "Captain, I got your Male Pirate Garb."
If you don't have the garb in your inventory when you select this option, you'll be thrown back into the brig
You are rewarded with 1,500,000 experience
From here, take off your pirate item(s) and head back to the Main Hall
Speak to any of the pirates in the side rooms to be thrown back into the brig
Speak to Daltoo at 67,7
Select "Sorry I left you."
Select "Oh, yeah I found the way out."
Select "I'd love to."
From here, you will need to walk slowly with Daltoo and escort him out of the Pirate Brig
There will be flashing tiles on the ground. In order for Daltoo to follow you, you must stay within these flashing tiles. Daltoo also will not move if you're standing in front of him, so if he isn't moving, try getting out of his way
Escort Daltoo through the brig all the way to the northwest exit
Daltoo will exit and you will be teleported outside of the ship back at Lynith Beach South
Re-board the pirate ship and get back into the Main Hall
Get thrown into the brig again
Speak to Daltoo
Select "Didn't I escort you out?"
Daltoo hands you Shinguards (boots) and you are rewarded with 30,000,000 experience; you have completed the quest