Martin Harvey is a middle-aged office worker who lives in Chicago with his wife, Katherine, 16-year-old daughter, Caroline, and 11-year-old son, Ben. When he learns his recently deceased uncle has bequeathed him a 60' yacht once owned by Clark Gable, he decides to take his family to the island of St. Pomme de Terre ("Saint Potato") to retrieve it so he can sell it. Katherine resists the idea, but agrees after Caroline announces she has just gotten engaged.
When the Harveys arrive at the island, they discover that the yacht, the Wanderer, is in terrible condition. Upon hearing this, the yacht broker cancels his plan to send an experienced captain to help them sail it to Miami, and instead hires a local sailor, Captain Ron Rico, a one-eyed man with a very laid back attitude, and Navy veteran who claims to have piloted the USS Saratoga. He launches immediately when he sees the car he arrived in roll off the dock and sink. Its owner arrives at the dock and shoots at him.
Captain Ron takes Ben's money in a game of Monopoly, giving him beer to drink and charging him for it later, but shows loyalty to Martin, who he refers to as "Boss". Martin, who doesn't like him, calls him "Moron" in his diary, and believes that he doesn't know what he's doing.
The Harveys decide to stop off in the Caribbean, but learn that Captain Ron doesn't know how to navigate. While on a random island, Martin decides to go on a nature hike, but runs into guerrillas led by General Armando. Captain Ron bargains for Martin's freedom by giving them a lift to the next island, and receiving some firearms in return to fight off pirates. This angers Martin, as he declares there will be no firearms on his yacht and tosses them overboard, before realizing that without them, he is going to have to give the guerrillas a lift.
In the yacht's cabin, Katherine shows Martin the initials of Clark Gable and Carole Lombard marked on the bedpost. They are so excited that they share their feelings and have passionate sex.
When they arrive at their next destination, San Juan, Puerto Rico, Martin and Katherine are arrested for smuggling the guerrillas. Caroline and Ben party with the locals and Captain Ron, which ends with Caroline getting a tattoo, Ben breaking his glasses, and Captain Ron losing his glass eye. Martin and Katherine are released from jail, but forced to leave that night. Martin decides to leave Captain Ron behind and they encounter pirates who steal the yacht, and are stuck floating in a raft.
They land in Cuba and discover the yacht there. The pirates find them, but with the help of Captain Ron, they are able to escape with the yacht. Captain Ron learns that they underrate Martin, and he decides to play hurt, forcing Martin to take control of the escape. Using the skills that Captain Ron taught them, they are able to get the sails up after the engine breaks from lack of oil to distance themselves from the pirates. The United States Coast Guard fires once at the pirates, scaring them away and creates a safe passage to Miami.
They arrive in Miami and part ways with Captain Ron. As they sail to their destination, they decide to turn the yacht around and keep it. In the final scene, Captain Ron (now cleaned up with his hair pulled back and wearing a suit) appears and is now employed by a wealthy couple in a small motorboat. He tells them they should take it out for a spin.Kurt Russell as Captain Ron Rico
Martin Short as Martin Harvey
Mary Kay Place as Katherine Harvey
Meadow Sisto as Caroline Harvey
Benjamin Salisbury as Ben Harvey
Sunshine Logroño as General Armando (as Emannuel Logrono)
Jorge Luis Ramos as General Armando's Translator
J.A. Preston as Magistrate
Tanya Soler as Angeline
Raúl Estela as Roscoe
Jainardo Batista as Mamba
Dan Butler as Bill Zachery
Tom McGowan as Bill
Paul Anka as Yacht Broker
Roselyn Sanchez as Clarisse
C.M. Talkington (credited as Clement Talkington) as the Bicycle Messenger
The film grossed $22.5 million, against its budget of $24 million.
The film premiered on September 18, 1992. It was panned for putting Russell in the comedic role and Short in the serious one, while others say that Russell's fun performance as the irresponsible and sometimes unsympathetic yacht captain carried it through its flaws. It has a score of 24% on Rotten Tomatoes based on 21 reviews with an average rating of 4.2 out of 10.
Salisbury and Sisto were each nominated for a Young Artist Award.