Poet Moondog embraces a life filled with indulgence and a free-spirited essence in and around the sun-kissed Florida Keys. Despite perceptions that his glory days are over, he is gradually crafting his next book while enjoying the perks of his local legend status. His reckless antics are funded by his affluent wife, Minnie, much to the dismay of their soon-to-be-married daughter, Heather, and Moondog's disapproving agent, Lewis. Throughout his escapades, Moondog finds himself entangled with various women, oblivious to the passionate affair Minnie is having with his friend, R&B singer Lingerie.
The drama unfolds when Moondog arrives tardy to Heather's wedding in Miami, where he provocatively gropes the groom, Frank, in front of shocked guests. Later on, amidst a discussion about his outrageous antics, Minnie confesses to Heather about her secret affair—knowledge that remains hidden from Moondog. During his adventures, Lingerie introduces Moondog to an extraordinary strain of cannabis, said to ignite his creative flame, cultivated from a secluded Jamaican pond.
At the wedding's reception, Moondog attempts to mend fences with Heather and Frank during the cake-cutting ceremony. However, the situation escalates as he witnesses Minnie and Lingerie in a moment of passion. In disbelief, he dives into a nearby fountain and bolts. That same night, Minnie tracks down Moondog at a local bar, leading to an evening of wild karaoke and dancing, which ultimately results in Minnie recklessly steering into oncoming traffic. Tragically, she passes away in the hospital, leaving half of her estate to Heather, while her other half remains frozen until Moondog proves himself by completing his novel.
Frustrated by his stagnant career, Moondog retaliates against Lewis's lack of support by rallying homeless individuals to vandalize Minnie's mansion. Facing possible jail time, he opts for a year of rehabilitation but escapes with a fire-loving companion, Flicker. The duo parts ways, leading Moondog back to Miami. There, he encounters an old acquaintance known as Captain Wack, who offers him a job co-captaining dolphin tours. In a twist of fate, Captain Wack's eagerness to swim with dolphins results in a painful encounter with sharks, severing his foot.
Now a fugitive in Miami, Moondog reconnects with Lingerie, who reveals the depth of his relationship with Minnie but insists that she truly loved Moondog. Despite these bombshells, Moondog remains unfazed. With Lingerie and Jimmy Buffett sharing stories about outrageous experiences meant to elude recognition, Moondog decides to adopt a similar strategy, which inadvertently draws the attention of law enforcement. With Lingerie's guidance and a stash of Jamaican weed, Moondog escapes to Key West.
With a renewed sense of purpose, Moondog pens his poetic memoir titled The Beach Bum, which is met with critical acclaim, ultimately earning him a Pulitzer Prize. As Heather goes through a divorce, she recognizes her father's transformation, unfreezing his inheritance, which Moondog insists must be given to him in cash and placed on a grand sailboat. However, during a lavish celebration of his newfound wealth, Moondog whimsically ignites the cash, triggering spectacular fireworks and pandemonium. Unfazed, he drifts away on his boat, as the audience, driven by the allure of falling money, barely notices his escape.
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