Donald tries to compose a Hawaian song to win the $1000 prize offered by the fruit company. Even though Huey, Dewey, and Louie try to create a Hawaian atmosphere for inspiration, it fails and Donald must go to Honolulu. In order to go with him, the nephews convince Donald to go as stowaways in one of Uncle Scrooge's ships, but they are found and Donald has to pay the trip.
In Honolulu, Donald finds the inspiration he needed, while the nephews find there's a lot of tourists composing songs for the prize, so they decide to write their own song to share the prize with Donald if they win. Donald also finds Daisy composing and hopes that if he doesn't win, she does. However, all their hopes are destroyed when they see Gladstone Gander writing and sending a letter. As Gladstone always wins, Donald and Daisy rip their song letters and tell the story to the nephews, who rip their letter too. Nothing in Honolulu distracts them from their sadness.
Donald, Daisy and the nephews find Gladstone in the ship back home, but they find he was just writing a letter to his neighbor to cut the grass. Now that he knows of the prize, Gladstone goes to write a son, but is tied by Donald. Everybody rewrites their respective songs, but Louie notices the ship won't reach Duckburg until after the closing date to send the letters. They throw their letters overboard and untie Gladstone, who writes a song and then reminds the others about telegraphs. The sad Donald knows Gladstone will win, but then they hear from the ship captain that Scrooge is going to buy the fruit company. Donald tells Gladstone that he won't be able to get $1000 from Scrooge, but Gladstone trusts his luck.
At the end, Gladstone wins the prize, and he's paid $1000... in pineapples. Donald and the nephews laugh at the sight of Gladstone trying to sell the pineapples.