Captain Hook gets a boo-boo on his finger while hammering in a nail trying to hang up a portrait of his mother in his cabin. He wishes to hear his mother sing to him to make his boo-boo go away. Hook hears a singing starfish in the distance, which happens to be Marina's pet starfish that she calls Sandy. Marina entrusts Jake and his crew to watch Sandy as Marina goes off to her water ballet class. While Jake and his crew watch after Sandy, they are distracted by an odd hula dancer soon revealed to be Mr. Smee, but it was too late. Captain Hook captures Sandy with a bucket and soon flees into the brush of the Never Land Jungle. Just as Hook wishes Sandy's song can heal his boo-boo, Jake and his crew soon track Hook and Smee to Hook's hidden treasure cave on Never Land, but Hook had planed for the young pirates arrival leaving a web like vines blocking the entrance. Using their clever wits, Jake and crew discover a flaw with Hook's trap and manage to slip pass into Hook's hidden treasure cave. Captain Hook over hears that his plans have failed and decides flee, but forgets about his trap that he set for Jake and crew. Hook and Smee find them ensnared within the web bouncing deeper into Never Land jungle until they are launched by a palm tree landing in Curvy Path Hills. Jake and his crew soon reach the hills with the assistants of Cubby's map. Jake and his friends knew which path to take to catch up to Hook. Hook and Smee soon hear Jake and his friends have caught up with them and decide flee yet again until he and Mr. Smee find themselves deep within Tiptoe Pass. The slightest noise will cause the massive towers of coconuts to tumble down. Hook tries to prevent Sandy form singing by stuffing him under his hat as he creep through Tiptoe Pass with Jake and his crew in pursuit. But as Hook and Smee try to slip through Tiptoe Pass, Sandy starts to squirm underneath Hook's hat. As the captain tries to keep the starfish from moving, the large feather on his hat tickles Smee's nose, causing him to sneeze loudly and the towers of coconuts to rain down upon them. Jake points out the emergence Izzy leaps into action using her pixie dust on everyone rescuing from the falling coconuts. Jake quickly swoop over to Captain Hook recovering Sandy from his hat. Hook orders Jake to return the starfish to him at once. Jake refuses informing the greedy captain that he and crew will return Sandy back to Marina before warning Hook to move out the way. Hook merely laughs at Jake's words, but soon he is swarmed by a flock of passing ducks which removes the pixie dust and gets him the ultimate boo-boo by sending him plummeting into one of the tower of coconuts. Smee quickly flies down to his captain, who emerges form the pile of coconuts in pain. Hook asks Smee to sing the boo-boo song to heal him,which Smee promptly does. With Hook no longer a threat Jake and his crew fly back to Pirate Island where Marina was waiting for them worried. Jake and his crew explain the whole ordeal to Marina. With her pet safely back in her arms, Marina thanks Jake and his crew for saving Sandy. Lastly, Jake and his friends put all of the gold doubloons they collected in their adventure back into the Team Treasure Chest.
Back aboard the Jolly Roger, Hook was in his cabin resting his body with so many boo-boos after the ordeal he suffered today. In hopes of trying to make Hook feel better, Mr. Smee tries to hang Hook's mother portrait closer, but stumbles back on Hook's bandages resulting in the portrait landing on top of Hook who soon collapses to his boo-boos. Smee is last seen trying to sing the boo-boo song once more.