Although Michael has matured well since the first film, he still feels that by birthright he deserves to start at the top of his father's law firm, whereas his father tells him that he will start him as a job clerking in order to learn the profession from the bottom up. Michael takes a summer vacation with his cousin, Tommy to Australia. Michael has big plans to show Tommy a good time aboard a luxury yacht, until he discovers that the yacht he chartered is actually an old, rusty fishing boat. But when modern-day pirates (led by Frakes, who stole Michael's wallet and discovered his family is very rich and intends on taking Michael for a ransom) chase the fishing boat, the boys are forced to jump ship, leaving them stranded on a desert island with the boat's captain, Jake Hunter, who scuttled the fishing boat to lose the pirates, and later admits he hated being a fishing boat captain and only stuck with it because his father loved it. In the end, they escape in the pirates' boat and leave them stranded on the island. As they escape, they call for the Australian Coast Guard's help. The pirates are arrested and their speedboat is seized. During a lunch, the boys have with Michael's father and Tommy's mom, Michael arrives and tells Jake and Tommy that Frakes' boat is now theirs and that they are going to start their own charter business owned by all 3 of them. Michael also tells his father that he will return home to take the job offer in his law firm.
- Joey Lawrence - Michael Woods
- Matthew Lawrence - Jake Hunter
- Andrew Lawrence - Tommy Biggs
- Anthony Wong - Frakes
- Jaime Passier-Armstrong - Jonas
- Martin Dingle-Wall - Dante
- Susan Walters - Jules Biggs
- Stephen Burleigh - Glen Woods
- Todd Worden - Mark Sanders
- Carly Movizio - Heather Hitt
- Jack Heywood - Valet
- Stephen Collins - Gardner
- The film stars the Lawrence Brothers again, who would star in various movies from the Disney Channel and provide voices to characters in Disney movies and shows.