Mickey is eager to set sail on Donald's boat, which leads the duck to reveal his secret: he doesn't know how to sail.
The episode opens with Donald relaxing on his boat drinking a coconut drink. He suddenly hears Daisy calling him and he wonders why she, Mickey, and Minnie are there. Daisy tells him she came to see her "captain in action". Mickey reminds him that he always told them he'd take them sailing one day and leads the girls onto the boat. Donald tries to get Mickey not to untie the boat from the boardwalk post but he ignores him and does it anyway.
Donald starts sweating while Mickey is ecstatic about sailing. Mickey tells Donald he's not looking so good and Donald whispers to Mickey that he doesn't know how to sail. Mickey shouts out loud what Donald told him, catching the attention of Minnie and Daisy, and Donald quickly covers Mickey's mouth to hush him.
Donald reveals to Mickey that Daisy bought him his outfit because "she loves a man in uniform". Donald states that if Daisy finds out he can't sail, it's over for them and pleads to Mickey for him to help him. Mickey tells him to not worry and to pull himself together. He then says that they just need to tie the boat back up to the post but he suddenly realizes that they are far away from the boardwalk. Mickey then tells Donald to just fly up and open the sail. He tries to but fails and Mickey tells him to just stop.
Moments later, they build a motor on the back of the boat. Mickey tells him to pedal and he'll steer. Donald tries to pedal but suddenly, a shark pops out of the water. This causes Donald to get scared enough to pedal with full speed and it makes the boat sail fast. The boat abruptly stops and Mickey looks behind him to see Donald running across the water trying to escape the shark. Mickey saves him by using a lasso to grab and him. As Donald is pulled back by the lasso, he smacks into the mast. Mickey tells him to pull the rope to release the sail.
Donald starts to get seasick and Daisy calls for him below and tells him he's so brave. Daisy asks Minnie if she ever told her that Donald was the best sailor. Minnie replies by telling her that she said that if he keeps up with the lies and the tantrums, then he can go fly a kite. Daisy replies back by once again saying that he is the best sailor. Daisy blows him a kiss and the heart smacks into him and makes him lose his grip on the pole. He grasps back on and releases the sail. Donald starts cheering that he finally did it and suddenly gets struck by lightning, which makes the sail burn and a storm start.
The force of the wind makes Donald's shirt pop up and causes the boat to sail forward fast making Minnie and Daisy scream. The boat starts going over waves and the boat starts sailing over to a whirlpool. Mickey, Minnie, and Daisy hang on for their lives. Mickey notices a rope attached to Donald and whips it, making the pole break off. Mickey uses Donald's shirt like a kite, lifting the boat out of the tornado. They fall back down into the water and using Donald's shirt again as a sail, they quickly sail back to the boardwalk.
Mickey pulls Donald back down and Daisy tells him that she knew he'd save them. He reminds her that his shirt is torn and she gives him a pilot outfit and calls him "Pilot Donald". Donald tells them to get ready for take-off and Mickey looks amazed and asks Donald if he can fly a plane. Donald tells him no and Mickey facepalms, ending the episode.
- Tony Anselmo - Donald Duck
- Chris Diamantopoulos - Mickey Mouse
- Tress MacNeille - Daisy Duck
- Russi Taylor - Minnie Mouse
- This is the only episode to air in August 2014.
- The previous titles of this episode were Donald the Sailor and Sailboat Time.
- The whirlpool that almost sucks the boat in was similar to the one from The Sorcerer's Apprentice.
- Donald has actually gone sailing in numerous other cartoons.