A Permanent Vacation Under the Florida Sun

Dawna and Greg Thomas enjoy playing pickleball at The Villages.

Gregg Segal

But the dominant pastime, in terms of geography, is golf. The Villages is best understood not as a town but as a peopled golf-delivery landscape: 36 nine-hole executive courses and a dozen larger country club courses are embroidered into the suburban culs-de-sac, with some 65,000 golf carts—many gaudily customized to resemble old-timey jalopies—serving as the primary mode of transportation. The homes, which range from under-$200s two-bedroom villas to million dollar-plus McMansions, nestle in a manicured ocean of greens; like Cheever's suburban swimmer, you could golf from one end to the other, 36 holes a day, for 15 days without repeating a hole.

'It's like being a kid in a candy store'

Like the other Disneyland, the Villages is best appreciated with a certain suspension of disbelief. Venturing beyond the borders of the development is called "going outside the bubble," says Greg Thomas, 66, who moved here with his wife, Dawna, 61, from Virginia Beach, Va., in 2012, and still seems blissfully dazzled at his good fortune. "It's like being a kid in a candy store," Greg says. "And then you get sick from all the candy."

"But in a good way," Dawna quickly adds.

Unlike her more recreation-focused neighbors, Donna Kempa, 56, still has a foot in the real world: She works part time as a financial auditor for a western New York health insurer. While husband Tony, 72, plays softball with pals, she telecommutes from a home office in their five-bedroom house. She's also the treasurer for the POA, or Property Owners' Association, which is the closest thing to a watchdog organization Villagers have.

Like most POA members, Kempa loves TV, but not quite as uncritically as many fellow Villagers: Sometimes she misses the restaurants of her old hometown, the opportunity to hang out with younger people. And something else: She wonders about the future. "I worry about sustainability," Kempa says. "What's going to happen when the baby boomers are done with this? What will happen to this place?"

Last year, the Villages sold more than 2,200 new homes—a huge amount, and enough to keep its ranking as the best-selling master-planned community in the nation. But the figure has declined for the last several years. Blechman observes that the current young retirees coming to the Villages are "the last of the lucky pensioners," since it takes a healthy regular income to maintain the permanent-vacation lifestyle for years, or decades. In the uncertain age of the 401(k), golf-centric retirement meccas like this may fade. "These places will turn into necropolises," he predicts. "All utopias fail."

Ah, but that's a problem for tomorrow's Villagers, whoever they are. For now, with a sun setting over man-made Lake Sumter and the outdoor bartenders mixing mudslides, it's time to grab a stool and watch the Villages Twirlers and Drum Corps—a troupe of majorettes in full uniform—parade through the square like the world's oldest high school marching band, batons flashing in the twilight. Roll your eyes at this if you must. Or smile and clap along.

"It's a made-up place," Komoroske says. "But the people are real."