Captain Ron

Martin Harvey (a middle-aged office worker) lives a humdrum existence in Chicago with his wife, Katherine, and their two children, Caroline and Ben. However, his mundane routine is disrupted when he inherits a 60-foot sailboat once owned by Hollywood icon Clark Gable from his recently deceased uncle. The vessel, christened Wanderer, is moored on the picturesque island of St. Pomme de Terre ("Saint Potato"), and Martin sees an opportunity to sell it. Katherine, initially hesitant, agrees to join him on this venture after their daughter Caroline announces her engagement.

The Harveys' arrival at the island reveals a stark contrast between their orderly lives and the chaos that awaits them. Upon inspecting Wanderer, they're dismayed by its dilapidated state, prompting the yacht broker to cancel his plans to dispatch an experienced captain to help them navigate the waters to Miami. Instead, he hires Captain Ron Rico, a one-eyed, laid-back sailor with a storied past as a Navy veteran who claims to have piloted the USS Saratoga.

Captain Ron's unorthodox methods and eccentricities are quickly apparent when he takes Ben's money in a game of Monopoly, only to charge him later for beer. Despite this, he displays a loyalty towards Martin, whom he affectionately refers to as "Boss." Martin, however, is skeptical of Captain Ron's abilities, dubbing him "Moron" in his diary.

As the Harveys set sail for the Caribbean, they're forced to make an unexpected stop at a random island. There, Martin decides to embark on a nature hike, only to stumble upon a group of guerrillas led by General Armando. Captain Ron, ever the pragmatist, bargains for Martin's freedom by offering the guerrillas a lift to their next destination in exchange for some firearms. This move leaves Martin incensed, as he's adamant that his yacht will not be armed. He subsequently tosses the weapons overboard, realizing too late that this decision will force him to provide transportation to the guerrillas.

In the midst of this chaos, Katherine and Martin find themselves reinvigorated by their shared passion for the romantic legacy of Clark Gable and Carole Lombard. The initials "C.G." and "C.L." marked on the bedpost in Wanderer's cabin serve as a catalyst for the couple to reconnect on a deeper level, culminating in a passionate night spent exploring each other's desires.

As the sun dips into the horizon of San Juan, a foreign land that bears little resemblance to its American counterpart, Martin and Katherine find themselves shackled in a local jail cell, accused of smuggling guerrilla fighters. Meanwhile, Caroline and Ben revel in the vibrant nightlife of the city, rubbing shoulders with the eccentric Captain Ron and the locals. Amidst the merriment, Caroline takes the plunge and gets inked with a permanent tattoo, while Ben's carefree evening is marred by the shattering of his glasses, and Captain Ron suffers the indignity of losing his prized glass eye.

Following their release from custody, Martin and Katherine are forced to make haste, leaving behind the debauched atmosphere of San Juan. However, fate has other plans in store for them. As they bid farewell to Captain Ron, they encounter a band of pirates who relieve them of their prized yacht, leaving them adrift on a makeshift raft. The duo finds themselves washed up on the shores of Cuba, where they stumble upon their stolen vessel, now piloted by its former captors.

Captain Ron, ever the opportunist, sees an opening to redeem himself in Martin's eyes and decides to feign injury, forcing the latter to take charge of the escape. Drawing upon the sailing skills honed under Captain Ron's tutelage, they manage to hoist the sails and make their getaway as the pirates give chase. The United States Coast Guard, responding to a distress call from the resourceful Captain Ron, arrives on the scene, apprehending the pirates and clearing a safe passage to Miami.

As Martin and Katherine set sail for their destination, they find themselves torn between parting ways with Captain Ron and keeping the yacht that has become an integral part of their journey. In the final act, Captain Ron is seen to have undergone a remarkable transformation, shedding his rough-around-the-edges persona in favor of a more refined demeanor as he assumes the role of captain for a young couple and their small motorboat. The most striking change, however, is the absence of his trusty eye patch – a testament to the power of redemption and new beginnings.