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-foot 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 become engaged. When the Harveys arrive at the island, they discover that the yacht,
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 named Captain Ron Rico (
Ronrico is a rum brand); a laid-back, one-eyed Navy veteran who claims to have piloted
USS Saratoga. He launches immediately after he realises the borrowed car he arrived in rolled off the dock and sank. 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, whom he refers to as "Boss." Martin, who doesn't like Ron, calls him "
Moron" in his diary, and believes 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 the Harveys arrive at their next destination,
San Juan, 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. 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 help from Captain Ron, they are able to escape with the yacht. Captain Ron learns that they underestimate 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, and distance themselves from the pirates. The
United States Coast Guard, responding to a distress call from Captain Ron, arrives and stops the pirates, creating a safe passage to Miami. The Harveys 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 appears to have cleaned up his appearance and has quickly taken on a new role as a captain for a young couple and their small motorboat. Notably he is no longer wearing an eye patch. == Cast ==