The film opens with Chicago businessman Martin Harvey (Short), and his family (wife Katherine, daughter Caroline, and son Benjamin), finding out that they've just inherited a vintage yacht that once belonged to Clark Gable. Upon arriving in San Pomme-De-Terre to claim it, the Harveys realize they need to hire someone to help them sail it to Miami so they can sell it. Unfortunately, that 'someone' turns out to be the bumbling, mischievous, eyepatch-sporting rascal, Captain Ron (Russell). With his somewhat dubious nautical skills and excessively laid-back attitude, Captain Ron ends up taking the Harveys on a wild adventure around the Caribbean, and while he manages to charm the rest of the family along the way, he ends up causing some serious tension with Martin himself.
This film contains examples of:
- The Alleged Car: In this case, the alleged boat. It's in extremely poor condition despite the fact it previously was owned by Clark Gable. Probably because it's been in storage for decades.
- Big Damn Heroes: Both Captain Ron and The United States Coast Guard toward the end.
- Bilingual Bonus: San Pomme-De-Terre translates to "Saint Potato" (a mix of Spanish and French), and the name of the pirates' ship, "Albondiga", is Spanish for "Meatball".
- Bratty Teenage Daughter: Caroline. First, shes getting engaged to her boyfriend when not even out of high school (said boyfriend is practically tailor-made to be her parents worst nightmare), then shes sneaking off with every boy she meets on every island they visit, coming back from one such adventure with a tattoo. Shes also uninterested in pulling her weight on the boat.
- Captain's Log: Martin starts a log of their adventures, but his jealousy of Captain Ron's easy charm with his family leads to it becoming just a book of complaints about everything Ron does. After Ron saves them from the pirates, Martin starts a new log which is much less crabby and notes that the previous log mysteriously got destroyed by the pirates.
- Eyepatch of Power: Captain Ron, though he's quite a departure from Kurt Russell's other one-eyed role.
- Cloud Cuckoo Lander: Captain Ron is a hard-drinking, womanizing, ex-Navy sailor-for-hire of questionable skill and judgment. Of course, he turns out to be right surprisingly often...
- When questioned about maritime right-of-way rules, he dismissively says, "Don't worry, they'll get outta the way." He learned this lesson from having previously been a helmsman on USS Saratoga. That their 40-foot sailboat is decidedly smaller than an aircraft carrier evidently hasn't occurred to him.
- Fun with Homophones: Martin is dismissive when Captain Ron tries to warn him to look out for gorillas on an island, claiming they aren't a native species. He soon gets captured by a small ragtag army - Ron had been saying "guerrillas".
- Male Gaze: Captain Ron loves him some Katherine and Caroline...
- Precision F-Strike:Captain Ron: We're all gonna fuckin' die!
- Ruthless Modern Pirates: Martin, who had previously scoffed at the idea of pirates being a real thing, suddenly regrets throwing all of Captain Ron's guns overboard.
- Shower of Awkward: When Captain Ron catches Martin and Katherine "playing 'hide-the-salami' in the shower." He rightly reminds them that the boat carries a finite supply of fresh water.
- Spit Take: Benjamin, upon learning of his parent's shower antics.
- Strip Poker: Ben learns the game from Captain Ron
- Waking Non Sequitur:Captain Ron: I didn't do it! I didn't do it, I swear!
- Walking Shirtless Scene: Not only does Captain Ron spend most of the movie without a shirt on, he even spends a couple of scenes wearing only a snug little Speedo, and another scene shows him in his underwear, a pair of itty-bitty briefs. Good thing he has the physique for it, otherwise...