Martin Harvey, a middle-aged office worker, finds himself trapped in a monotonous life in Chicago alongside his wife, Katherine, and their two children, Caroline and Ben. Their routine is disrupted by the unexpected inheritance of a 60-foot sailboat, previously owned by the legendary Hollywood star Clark Gable. This vessel, aptly named Wanderer, is docked on the beautiful island of St. Pomme de Terre ("Saint Potato"), and Martin initially sees it as an opportunity to sell. Although Katherine is wary at first, she relents to join him after their daughter Caroline announces her engagement.
Upon arriving on the island, the Harveys quickly realize the dissonance between their meticulously ordered lives and the overwhelming chaos they are about to face. Their first inspection of Wanderer reveals a boat in shambles, leading the yacht broker to retract his decision to assign an experienced captain to assist them in navigating to Miami. Instead, he sends in Captain Ron Rico, a one-eyed, carefree sailor with a colorful history, claiming to have once helmed the USS Saratoga during his Navy days.
Ron’s bizarre ways become apparent almost immediately, as he swindles Ben in a game of Monopoly before charging him for drinks. Despite these antics, Captain Ron grows loyal to Martin, whom he endearingly calls "Boss." Yet, Martin maintains a skeptical outlook on Ron's abilities, referring to him as "Moron" in secret writings.
As the Harveys embark on their Caribbean voyage, an unexpected detour leads them to an unfamiliar island. There, Martin’s adventurous spirit prompts him to go on a nature hike, which results in a shocking encounter with a group of guerrillas commanded by General Armando. Pragmatic as ever, Captain Ron brokers a deal for Martin’s release by exchanging a lift to their next location for firearms—a decision that infuriates Martin, who staunchly believes their yacht should remain unarmed. In a moment of anger, he tosses the weapons overboard, only to find himself having to accommodate the guerrillas.
Amidst this turmoil, Martin and Katherine rediscover their passion for one another, inspired by the romantic history of Clark Gable and Carole Lombard. The initials "C.G." and "C.L." etched on the bedpost in Wanderer's cabin serve as a bridge to rekindle their connection, leading to a night filled with intimate exploration of their desires.
As night falls over San Juan, a city vastly different from their own, the couple's adventures lead them to a local jail, where they are wrongfully accused of smuggling guerrilla fighters. Meanwhile, Caroline and Ben delve into the vibrant nightlife, mingling with the eccentric Captain Ron and the locals. In the midst of the revelry, Caroline decides to get a permanent tattoo, while Ben faces a setback as his glasses shatter, and Captain Ron endures the humor of losing his prized glass eye.
Once released from custody, Martin and Katherine are forced to leave the raucous environment of San Juan in a hurry. However, as they bid farewell to Captain Ron, they encounter a band of pirates who steal their beloved yacht, leaving them stranded on a makeshift raft. Their misadventure leads them to the shores of Cuba, where they unexpectedly find their yacht—now navigated by its former captors.
Seizing his chance for redemption, Captain Ron pretends to be injured, compelling Martin to take charge of their escape. Armed with newfound sailing skills imparted by Captain Ron, they manage to raise the sails and flee as the pirates pursue them. The United States Coast Guard appears in response to a distress signal from the resourceful Captain, apprehending the marauders and ensuring a safe journey to Miami.
As Martin and Katherine set sail toward their destination, they grapple with the decision of parting ways with Captain Ron, juxtaposed with their attachment to the yacht that has woven itself into the fabric of their experiences. In a poignant conclusion, Captain Ron seems to undergo a transformation, shedding his rough exterior to embrace a more polished role as captain for a young couple and their small motorboat. The undeniable highlight of this change is the absence of his iconic eye patch—a sign of the possibility for redemption and new beginnings.
