Anyone who was part of the late-night crowd during Key West’s ramshackle glory days, loosely defined as the 1970s and most of the 1980s, remembers the old Conch Flyer.
That’s because bars on the island were legally required to close at 4 a.m. — an hour many of us regarded as deeply unreasonable — but the dark and slightly seedy Conch Flyer, a fixture at the local airport, was conveniently located on county-owned property, and was thus exempt from that law.
Naturally it became an after-hours hub for the high-rollers, renegades, off-duty bartenders, bouncers and strippers who led nocturnal lives.
The Conch Flyer was never fancy. There was an edge to it — an edge that was familiar to us, but disconcerting to outsiders.
Occasionally, for example, ordinary travelers waiting for red-eye flights wandered in around 6 a.m. After taking a quick look around, most of them fled as if they had just remembered an important appointment elsewhere.
You couldn’t blame them. By that time, customers who weren’t illegally alert were glassy-eyed drunk. By dawn on many mornings, the Conch Flyer was no place for the fainthearted.
Sometime in the 1980s, the bar was acquired by John Richmond, a man who understood its anything-goes vibe better than most. John had moved to Key West in 1978 as a young co-pilot for the now-defunct Air Sunshine, nicknamed Air Sometimes because of its erratic schedule.
I remember Air Sunshine fondly, because one of its tiny planes brought me to Key West for the first time in February 1976. I’ll never forget stopping in the plane’s doorway while disembarking, staring in wonder at the palm trees and blue ocean visible across a road whose name I didn’t yet know. I was captivated — just as John Richmond was two years later.
After his stint with Air Sunshine, John flew for Florida Keys carrier PBA Airlines, sometimes known as Air Provincetown. It too had an eccentric on-time arrival record, so we dubbed it Air Probably.
John’s memories include turning departing planes around at the runway’s end to go back for ticket holders who were running late, discovering Miami-bound passengers rolling dice in a plane’s aisles, and witnessing a prominent local hotelier arrange a flying craps game.
Those were the days when Capt. Tony Tarracino, cheerfully roguish owner of Captain Tony’s Saloon in downtown Key West, led groups of pretty, new flight attendants on barhopping “orientation tours” of the island — so enthusiastically that the girls’ next-day hangovers often caused flight cancellations.
When John took over the Conch Flyer, it remained an after-hours “clubhouse” for Key West insiders.
A place with its reputation (and clientele) required no-nonsense bouncers. But these weren’t just any bouncers. Instead of paid staff, they were volunteers: career bouncers from local bars and clubs, who drank at the Flyer after hours and chose to protect it as if it was their own.
They didn’t take attitude from anyone — even famous people like TV news personality Geraldo Rivera, who was unceremoniously ejected after he did an unfriendly exposé of Key West bars.
For decades, the Conch Flyer remained a haven characterized by a freewheeling mindset, slightly outlaw aura and lack of real-world rules. Eventually it evolved, just as Key West and its nocturnal crowd did, into a less edgy but still appealing version of itself.
Today, the venerable Flyer is a place where airline passengers and locals can enjoy drinks, comfortable camaraderie and food ranging from quick bites to casual meals. Its late-night hours are just a memory, but occasionally customers will encounter an old-time Key West resident — who just can’t resist spinning tales of the island’s glory days.
