As Jack Chester (John Candy) confronts the aftermath of several air traffic control blunders, he receives an unexpected blessing: a five-week paid leave from his high-pressure job. This timely break provides Jack the chance to reconnect with his family—wife Sandy and children Jennifer, Bobby, and Laurie—as they set off for a long-awaited summer vacation from Atlanta to the scenic Gulf Coast resort town of Citrus Cove, Florida.
Yet, their serene getaway quickly spirals into a whirlwind of chaos and unforeseen events. Shortly after arriving, the family faces their first setback when they are unjustly denied access to an upscale seafood restaurant by the smug local sailing champion Al Pellet (Richard Crenna), who takes on the role of Jack's main nemesis. This public humiliation drives them to dine at The Barnacle, a quirky pirate ship-themed restaurant managed by the amiable Scully (Rip Torn).
As their vacation progresses, a mix-up over their rental property's address leaves the family scrambling late at night for alternative lodging, ultimately landing them in a shabby beach shack teeming with foot traffic. Meanwhile, the original landlord's sudden illness allows Al Pellet to seize control over their situation, complicating matters even further.
Jack's injury from a sailing mishap involving Al hampers his ability to enjoy quality time with his family, pushing him to forge an alliance with Scully and bond with their eccentric neighbors, the Sanders. Tensions boil over when Al demands that the Chester family vacate after their two-week rental period expires.
Desperate to prevent their eviction, Jack cleverly challenges Al to a high-stakes sailing regatta in Citrus Cove: if he wins, he secures an additional two weeks of rent; if Al triumphs, the Chester family must leave. Though Al is initially dubious, he reluctantly accepts the challenge, setting the stage for a gripping confrontation that could change their vacation—and lives—forever.
As the Chester kids drift into a dull routine, they discover newfound excitement by helping Jack, Scully, and the intriguing Sanders revitalize The Barnacle. Angus, Scully's loyal right-hand man, plays a vital role in acquiring the perfect sail dimensions, readying their ship for competition on the open sea. At the same time, Jack's adventurous youngest daughter, Laurie (portrayed by an unnamed actress), seeks thrills as she implores Yorku, a mystical character with wild, grey locks, to engage her in playful fantasies down in the ship’s shadowy cellar. Enveloped in an enchanting world of whimsy, Laurie accompanies Yorku as he sweeps her into a realm of imagination and fun. Little do they know that The Barnacle is destined to surpass all odds and achieve an unforeseen triumph against Pellet, aided by a stroke of luck, a sudden gust of wind, and Jack's trusty, oversized trousers.
