Escape from Margaritaville

I recently dreamed I was in a public park. The grass was cartoonishly green, a kind of chlorophyll utopia, and families sprawled across it as if they’d been carefully arranged for a Chamber of Commerce brochure. My suitcase sat at my side. I felt lost. Like a misplaced airport refugee, I looked up.

Looming above the park was a billboard—a monstrosity of sun-bleached cheer—featuring a leathery couple in their seventies. They were bronzed like overcooked turkeys, grinning wide, basking in the eternal glow of some Florida condo where “Margaritaville” played on an endless loop.

The “Margaritaville” billboard—two geriatric smiles frozen in sunlit rapture—reminded me that I’d been meaning to watch Some Kind of Heaven, the documentary about The Villages, that gargantuan playground for the aged about forty-five miles from Orlando.

Deep down, I knew I needed to watch this documentary. I was born in Florida, and as my retirement crept closer and closer, I felt an urge to return home. I love the smell of mangos and coconuts at night. Nostalgia is a potent drug. It could cause me to sell my home and buy a condo in Orlando.

So I watched the documentary. It was the opposite of a travel infomercial. It was a horror movie. It started with synchronized water ballet to Neil Sedaka and margarita-fueled Parrothead parties. The Villages are marketed as heaven with a tiki umbrella on top, but for anyone with taste, patience, or shame, the place looks more like an early-onset hell: a tropical gulag where you pay people to micromanage your leisure until leisure itself becomes a program of infantilization.

The film’s most disturbing subject is Dennis Dean—an eighty-one-year-old small-time grifter wanted for a DUI in California, living out of a blue van on the edge of The Villages and scheming his way into the bed of a rich widow. He prowls bingo halls and church socials with the persistence of a con man who has practiced charm until it has fossilized. When police finally close in, Dennis slips back into Nancy’s apartment. In a scene that sticks with you, he lies on her bed while she calls from the kitchen: “Lunch!” He finds his new girlfriend, whom he’s leeching off, annoying. He doesn’t move. He stares at the ceiling fan as if it were a slow, merciless clock, and you can see, plain as day, that comfort can become a prison for someone whose last liberty was earned through deceit. As I watched Dennis staring at the ceiling fan, it hit me: He’s in purgatory.

The director never sneers at his subjects. Pain and longing are shown with a kind of blunt respect. But the portrait of The Villages itself isn’t charitable. It’s a retirement complex caught in mid-regression, a carnival mirror reflecting geriatrics clinging to perpetual adolescence until the spectacle curdles into something queasy and cringe-worthy. The managed fun—shuffleboard courts, themed parties, and scheduled joy—becomes a machine that demands you perform your own amusement. It’s not freedom. It’s occupation by leisure.

And yes, I realized, sitting there with my pride intact and my Florida fantasies suddenly damp, that watching this must have been my wife’s brilliant little psy-ops operation. For a year, I’d been nagging her about moving the family to Florida—stilt houses, salt air, a hammock with my name on it. She was skeptical about moving to Florida. She mentioned hurricanes and unavailable flood insurance, for starters. Florida also had a reputation for government corruption, contractor fraud, and credit card theft. When her credit card was used fraudulently and she called her bank, the customer service agent asked, “You weren’t in Florida recently, were you?”

In fact, she was.

Florida was not paradise. It was a crime syndicate.

She did not discourage me from watching Some Kind of Heaven. She didn’t have to. The documentary demolished my fantasy of returning to my home state within the first thirty seconds, with its water ballet and sedated margaritas. My obsession evaporated.

But only for a minute.

After a quick snack, I was back at my computer looking at luxury condos in Henderson, Nevada.