If you read Big Whoop: Unclaimed Bonanza or Myth?, you'll be given some info that'll get you started on the right track. Enter the cabin and ask about your choices for where to go.
Before looking for any map pieces, it's convenient for this walkthrough to get started with Phatt Island, so go there. After the ensuing scenes, pull the rock-hard mattress and use the stick underneath to extract a bone from the dead prisoner in the adjacent cell. Give the bone to Walt, use his small key to unlock your cell, and open the manila envelope on the shelf. You are now free to roam the island.
Go to the alley to the left of the library, where a gambling game is taking place.
- Follow the kid into another alley, where he'll obtain the next winning number from somebody behind the door. Observe that the password is the number of fingers shown in the first of each pair of hand signals; what the person says while showing the signals is intended to mislead you. Knock on the door, ask about the next winning number, give the correct password thrice, and use the number to win.
- Place a bet and you'll win.
Claim the invitation, go to Booty island, and show it to the keeper of the costume shop. Take your costume and exit the wharf from the left. Head to the mansion and you'll be stopped at a small structure, where you'll be forced to don your costume. Proceed into the mansion, pick up the map on the picture frame to the left, and attempt to escape. When you meet Elaine, sweet-talk her until she throws the map out the window.
- Before going outside, return to Elaine's room and take the oar on the wall. As you attempt to pick up the map piece on the ground, the wind will blow it to the cliff on the southern edge of the island. Pick up the dog and walk around to the side of the house. Pick up the garbage can to make some noise, and the chef will come out of the kitchen to chase you. Run a quick lap around the mansion, enter the kitchen, steal a fish from the pot, and go to Phatt Island. Walk up to the fisherman on the right side of the wharf, and challenge his fishing skills. Show him the fish to win his fishing pole, and use it to reel in the map piece at the cliff of Booty Island.
- A bird has taken the map piece to the big tree in the north. Go there and place the oar in the tree hole next to the plank. As you attempt to walk on top of the oar, it will break. After the ensuing dream, take the broken oar to the woodsmith on Scabb Island for repair. Return to the tree and now use the reinforced oar with the hole. Walk on top of the oar, pick up the plank, place it in the next hole, walk on top of the plank, and keep working your way up the tree this way until Guybrush does it automatically. Enter the closest hut and use the dog with the pile to find the map piece.
- Go outside and retrieve the map piece on the ground.
Since the cook was killed on Scabb Island, his remains will be found in the cemetery. However, his coffin is in the locked crypt (one of the small buildings on the right). The key is found in Stan's Previously Owned Coffins on Booty Island, but you'll need some equipment before you can steal the key.
- Enter the Booty Island antique shop, which is immediately at the island entrance. Purchase the well-polished old saw (in a barrel near the store entrance), and head to the Scabb Island laundry place. Use the saw on the scary sleeping pirate's peg leg, and go to the woodsmith's. Because the woodsmith is away for emergency services, you may steal his hammer and some nails (on the right of the cabin entrance).
- Go to the Scabb Island woodsmith and pick up the hammer and some nails.
Go to Booty Island and enter Stan's store, which is to the right of the costume shop. Ask Stan for a good used coffin, and close the lid as soon as you have the opportunity. After receiving a complimentary clean, white hankie, use the hammer with the nails and steal the crypt key hanging on the large tombstone in the back, and use it to enter the Scabb Island crypt.
- All the coffins are inscribed with quotations, so you'll need to find a book of quotations. Visit the Phatt Island library on the right side of the wharf area and use the card catalog near the entrance. You'll find the title Famous Pirate Quotations under Quotations, but it has been signed out by the governor. Memorize a random book other than Disaster: Great Shipwrecks of Our Century and Recipes, Voodoo: The Joy of Hex (you should borrow those two as well while you're here). Obtain a temporary library card from the librarian, sign out the book, and enter the mansion on the south side of the island. Talk to the guard blocking the stairs and find a reason to displace him from his post. Proceed upstairs and swap your random book with the one on the governor's belly.
- Return to the crypt, read Famous Pirate Quotations and memorize Rapp's line. Browse through the coffins until you find the one inscribed with Rapp's quotation, open it, take some of his ashes, and go to the swamp shack. Attempt to pick up Ash-2-life™, which is found in the jar in the middle of the bottom shelf. If you did not borrow Recipes, Voodoo: The Joy of Hex earlier from the library, do so now and bring it to the Voodoo Lady. Return to Rapp's coffin, use Ash-2-life™ to resurrect him, and agree to do a favor for him. Find the weenie hut (shack) on the beach and use the key to enter. Turn off the gas by turning one of the four knobs above the oven doors, and inform Rapp of your findings to obtain his map piece.
- Browse through the coffins until you find the one with Rapp's name, open it, and pick up the map piece.
The cabin boy apparently sold his map piece to the Booty Island antique shop.
- Since you don't have 6,000,000 pieces of eight, you'll need to trade something in. If you keep talking to him, he'll tell you that he wants the figurehead of the Mad Monkey. Exit the shop and continue going right past Stan's store to find a spitting contest, so give it a shot.
- Go to the bar on Scabb Island and show the barkeeper your library card so that you can buy a Yellow Beard's Baby and a Blue Whale. Mix the yellow drink with the blue drink to make a green drink. Go to the antique shop and purchase the ship's horn on the wall near the parrot, and return to the spitting track and examine the flag markers. Blow the ship's horn and quickly pick up the flags to bring them closer to the fault line. Use the crazy straw with your drink, and spit when you see the lady's red scarf blowing in the wind. Show your hard-earned spit plaque to the antique dealer and convince him to buy it for 6000 pieces of eight.
- If you have not borrowed Disaster: Great Shipwrecks of Our Century from the Phatt Island library, do so now. Read the book and memorize (or write down) the coordinates found in the book. Talk to Captain Kate Capsize, the woman outside Stan's store, and charter a ship. Go to the coordinates, take a deep dive, take the monkey head off of the sunken galleon and pull the anchor on the left. Trade in your treasure for the map piece in the antique shop.
- Buy the map piece sitting on the owner's desk.
- While you're still in the big tree, go to the gazebo in the far branch and take the telescope. Talk to Captain Dread and tell him that "I'd just like to cruise aimlessly for a while." Pick up the parrot chow on the deck, enter the Booty Island antique shop, and purchase the sign to the right of the parrot. Place the parrot chow on the hook where the sign used to be so that you can buy the mirror (the owner will not sell it if his parrot is looking at it). Ask Kate for a leaflet, and go to Phatt Island. Place the leaflet on the poster of you, go inside the jail, and open the gorilla envelope on the shelf. Visit the Scabb Island bar, impale the banana with the metronome, and pick up Jojo. Return to the Phatt Island jail and open the vanilla envelope for a bottle o' near-grog.
View the Phatt Island map and go to the waterfall west of the wharf.
- Walk along the path to the top of the waterfall. Once at the top, use Jojo with the pump. Descend back to the base of the fall.
Proceed through the gaping hole and the tunnels, then enter the cottage at the top of the hill.
- Tell the retired pirate to "prepare to die" and you'll find yourself in a drinking contest. When he gives you your mug o' grog, quickly pick it up and empty its contents into the tree on the left. Refill it with the near-grog, and prepare to win. After he's knocked out, place the mirror on the mirror frame and open the shutters by the door. Go outside and put the telescope in the grotesque statue's hand. Go back inside and push the brick that has a circle burnt into it. If you pushed the correct brick, you will fall next to a bathtub.
- Walk to the left side of the room and open the trap door on the floor.
Take the hand and map away from the skeleton.
Piecing it together
If you want to reduce your inventory load, go to the library and return all your books to the librarian.
- Enter the library, open the lighthouse model by the door, and steal the model lighthouse lens.
Go to Wally on Scabb Island.
- Give the model lighthouse lens to Wally.
Let him examine the map pieces, and agree to run an errand for him. Notice that a crate has appeared in the swamp on your way back to Woodtick. Go inside of it when you are ready to continue.