The episode starts off when Jake, Izzy, and Cubby are finished building a sandcastle. Jake, starts complimenting everybody on the things they put on the sandcastle.Skully comes down from the lookout tower and tells Jake and his crew that the Jolly Roger is coming towards Pirate Island. Jake looks through his spyglass, confirming Skully's warning that the Jolly Roger was heading towards Pirate Island and ponders what Captain Hook maybe up to. Meanwhile aboard the Jolly Roger, Captain Hook plots to take over Pirate Island and claim the island hideout for himself, which Mr. Smee eagerly writes down Hook's scheme as the Jolly Roger sails closer to Pirate Island.
spotting Hook's ship arriving towards the island Cubby gets scared and hides behind the sandcastle, but Jake reassures him that he has already come up with idea to deal with Hook,as he informs the rest of his crew they need to hide their hideout. He also asks the audience if they will help him hide the hideout and keep a lookout for Gold Doubloons. Everybody starts saying what they have and Izzy explains why they have Pixie Dust. They run towards a large Tiki idol, and tells the audience; how to open the hideout secret passage, they have to push the tiki's tongue down. The palm trees move away and the doors open. Jake and his crew run up the stairs and into the hideout and sing "Yo Ho Mateys Away". They start hiding the hideout. They gather up and Jake asks if everything is ship-shape, Izzy and Cubby reply "aye-aye". They get four gold doubloons for completing the pirate problem. They grab the doubloons and start to checking up on Hook; he storms on to Pirate Island, and knocks down the sandcastle with Smee.
They later start looking for the hideout. Hook then starts digging around near the tiki, and then starts thinking of possible places that may reveal the entrance to the hideout. He lies his elbow down on the tiki twice unaware that he opens the entrance to Jake's hideout in the process. Jake and his crew marvel from above the hideout looking down at Hook and Smee. Hook soon comes with the idea that they should go to the top of the nearby mountain to get a better look of the island to find the access to enter the hideout as he and Smee rush off. Izzy chuckles believing Hook and Smee efforts were in vain, as all the hatch doors are closed, but then Skully points out a hatch that they missed.Jake says that they need to distract Hook and Smee so they can close the hatch, as Hook and Smee are climbing the hill. However, Smee's legs starts to get tired, but Hook orders Smee press onward. Cubby pops out, and later Izzy and Jake pop out. Cubby needs help to get in front of Hook and Smee, and Izzy suggests that they should make monkey sounds to distract Hook and Smee. They make monkey sounds, and while Hook thinks that Smee is screeching, Smee says that it is a barrel of monkeys. In the top-right corner is Cubby, climbing up. Cubby appears in the hatch and closes it, and they earn two gold doubloons. The top of the hill opens, and Cubby gets scared. Jake does monkey sounds at Cubby, and Cubby says that it's time for Hook and Smee to get wet, so, Cubby takes hold of the cannon, and points it at Smee and Hook. Water comes out of the cannon, and washes Hook and Smee into the ocean. Later, Hook and Smee climb up to a hollow tree, and Hook thinks that is where the hideout is. Smee goes to take a look, but falls on Hook, who falls into the tree and down a winding slide, onto a barrel and falls off, flying over Bucky and out the waterfall and into the ocean.
Smee then throws a life preserver at Hook, and Izzy says that Hook didn't even know that he was in the hideout, and chuckles. Hook and Smee climb up the side of the hideout, and finds a closed hatch door that Izzy is looking through. Jake and the crew are inside the hatch door, and Cubby comes up with an idea. Cubby says that he needs to fly, so Izzy thinks of what they can use to make Cubby fly. Izzy says that a pinch of pixie dust can help him fly. Izzy sprinkles it on Cubby, who flies out and starts acting like a fly. That distracts Hook who thinks it is a fly. It worked, and helped Jake and his crew hide the hideout. Then they got two doubloons after making Cubby fly to distract Hook, who is still trying to get away from Cubby. He sees Cubby and gets a fly-swatter hook. He swings his hand around, but falls on a board that is attached to a string, and starts zipping away and falls down with the board into the hideout's stairs and starts falling down into the ocean, past the hideout down a ramp and out of the hideout and into the ocean...again. Smee throws a life preserver yet again and drags Hook to shore. Smee tells Hook that they should try another day, but Hook stands up and disagrees with Smee's idea and sneezes onto shore. Smee says that it looks like Hook got a cold, so they go back to the Jolly Roger and Hook sneezes again. The Jolly Roger sails off. Jake and the crew sing the Team Treasure Chest song to summon the Team Treasure Chest from under the sand. The young pirates lastly count all their Gold Doubloons then put them into the chest.