By the time I get to Gasparilla Island, a glorified sandbar off Florida’s west coast that’s about an hour’s drive from Fort Myers or Sarasota and a whole lot harder to reach from everywhere else, Labor Day has come and gone. I’m seeking the warmth of the sun, and a genuine Florida beach town that will serve as an antidote to the forests of condos and hotels that line the coasts north of Miami and south of Tampa.

I find three generations of Joiner women relaxing in mismatched chairs at the far end of their marina, which has been trading in gasoline, tackle, snacks, sundries, and gossip since 1926. Isabelle Joiner, daughter of the founder, tells me she has been sitting in pretty much the same place, gazing out at the same inlet, for seven decades, going on eight.

There’s a heron perched on a log and sunlight filtering through the tall grass past a gas pump near the water’s edge. It might be 1950 or 1990, who could tell? “Oh, there’ve been changes,” Joiner replies. “We used to shuck and sell oysters from right in there,” she says, nodding toward the shack abutting the dock. “Can’t now. They need to be inspected.”

Birds pay a visit to the Gasparilla Inn's 18-hole, Pete Dye golf course. (Photograph by Steven Martine)

White ibis pay a visit to the Gasparilla Inn’s 18-hole, Pete Dye golf course. (Photograph by Steven Martine)

I’ve already figured out that it’s more fun to hang with the locals, an insular community of some 500 square-knot tiers, rum slingers, odd-jobbers, and historic preservationists, than the “beachfronters,” those part-timers who swell the head count tenfold at the height of the winter season in a blaze of preppy plaid.

But what makes Gasparilla special is that it takes both demographics to give the place its personality. Their interactions on the compact streets of the island create narratives that are part John Cheever and part Sherwood Anderson, accompanied by the lilt and thrum of a Jimmy Buffett song.

Katharine Hepburn, who owned property in the island’s only town, Boca Grande, was a beachfronter. So are the Bushes, Pappy on down, who arrive in force every Christmas and occupy a dozen or so rooms at the Gasparilla Inn, the lemonade-colored clapboard hotel at 5th and Palm that holds an outsize presence in the community.

While the Joiners wear fishing-derby T-shirts and faded shorts, beachfronters are resplendent in full Palm Beach regalia: lots of pink and green, and Vineyard Vines ties for dinner at the inn. If they putter around town in golf carts or on bicycles as if they know just where they’re headed, it’s because they do.

That’s the thing about Gasparilla: Those who’ve been coming down for weeks at a time all their lives have the same proprietary feeling as those who never leave.

The Joiners’ vistas haven’t changed in generations, but the Bushes’ haven’t, either. Merely renovating the inn’s dining room was a perilous undertaking. “Fortunately, most of our longtime customers understood it had to be done,” says the former hotel general manager, Jack Damioli, putting an emphasis on the “most.”

A 1980 ordinance called the Gasparilla Act restricted building heights, limited density, and banned billboards and neon. I can’t find anyone willing to argue against any of that. Just in case, the Gasparilla Island Conservation and Improvement Association has created a photoshopped view of what the island might look like if the legislation didn’t exist, including a wall of condos rising from the shoreline. It circulates periodically as a frightful reminder.

At the inn I meet Cannon Jones, who works the front desk. Her dad, Yogi, bought property here in 1986, when she was a toddler. The family migrated down from Connecticut each winter holiday that followed. Cannon stayed north for college, but when Yogi died three years ago, she needed somewhere secure that felt like home. She knew exactly where that was.

Cannon was married beneath the boughs on Banyan Street, which had been barricaded for the occasion. Her groom, Nick Wenzel, is a local who has been “on island,” as they say, since puberty–fishing, guiding, loitering, part of the fabric of the place. I can’t help seeing Cannon and Nick as one of those royal marriages that unite two disparate domains.

Boca Grande Lighthouse, built in 1890 (Photograph by Steven Martine)

Boca Grande Lighthouse, built in 1890 (Photograph by Steven Martine)

One evening, just as the old-fashioned street lights start to blink on, I pedal my rented bike to The Temp to meet them for a drink. The restaurant is formally named The Temptation, but nobody calls it that. It’s nearly as much of a meeting place and gossip center as the post office, where the town gathers daily because there’s no home mail delivery. Cannon and Nick are the only ones at the bar. “In about five minutes, this place will start to fill up,” Nick says. It does, in a stream of ones and twos, nearly all of whom wander by to say hello.

Later we head across the grandiosely named Park Avenue for grouper at PJ’s Seagrille. Then it’s back for a nightcap at The Temp. I’m tipsy when I leave, but the moon is high and bright and the bike sturdy and forgiving. I pedal the three blocks to the inn in a state of wistful melancholy, wondering what it might be like to be young and unencumbered and living in this timeless town, or at least coming down for the season.

Ultimately, of course, what’s timeless about a beach town is the beach. The next morning I ride to the inn’s Beach Club, which isn’t the prettiest coastal access on the island but is easily the most outfitted. I walk past the tiki bar and the lunch buffet, clamber down the seawall, and launch myself into the water.

The sky overhead is spotted with clouds, while out toward Mexico it’s the hue of molasses. The gulf has a roar and roll of an ocean. I swim awhile. Then I settle into a whitewashed wooden chair and watch the weather come in, as it always has and always will.

This piece, written by Bruce Schoenfeld, first appeared in the June/July 2014 issue of National Geographic Traveler magazine. 

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