Apparently I wasn’t the worst-ever cocktail waitress at the Afterdeck, the ocean’s-edge bar at the legendary Louie’s Backyard, but I was pretty bad. Yet Phil Tenney, owner of the beloved restaurant until his death in 2024, didn’t fire me.
Maybe it was just a case of Key Westers looking after each other. That was common on the island in the early 1980s — and when my pot-smuggling fiancé was caught by the federales, subsequently disappearing to avoid their clutches, friends decided to look after me.
So despite my inability to uncork a bottle of wine, or remember the ingredients of any drink more complex than a rum and Coke, I served cocktails at Louie’s for a while.
Located in a gorgeous century-old waterfront home, Louie’s was in its second incarnation during my tenure at the Afterdeck. The original restaurant debuted in 1971, opened by Key Westers Frances and Louie Signorelli — with seating for 12, one lone waiter, and a cigar box for a cash register.
Thanks to its charm and the Signorellis’ hospitality, Louie’s flourished. As it grew, it earned a reputation for fantastic food and a casually chic atmosphere.
Key West in the ’70s had an end-of-the-world vibe and Louie’s — overlooking a vast blue ocean that suggested infinite adventures — became one of its hubs. At the bar, local treasure hunters and recovering hippies drank rum with Pulitzer Prize-winning escapees from the literary mainstream. (Other customers included a dog named Ten Speed, whose favorite cocktail was Kahlua and cream.)
Eventually, the Signorellis’ stewardship of Louie’s ended and it was purchased by Phil and Pat Tenney. After lovingly renovating and enlarging it, a process that took nearly a year, they opened the new Louie’s in December 1983.
By that time, Key West was a magnet for boundary-pushing writers, actors and musicians bent on redefining their creative genres. Among them were novelist and poet Jim Harrison, “A Rumor of War” author Phil Caputo and “pirate laureate” Jimmy Buffett, known for memorializing the Key West lifestyle in song.
At Louie’s Afterdeck, they found a place where they could be themselves, share drinks and discussion with like-minded cohorts, and draw inspiration from tales spun by the world-class fishing guides and free-spirited locals who also frequented the bar.
Buffett, before he bought his Key West home, rented a second-floor apartment in the house beside Louie’s — so the line “I stumbled next door to the bar” in his song “Trying to Reason with Hurricane Season” can only mean one place.
Eventually Buffett loaned his apartment to “gonzo journalist” Hunter Thompson, author of the book “Fear and Loathing in Las Vegas” and renowned for outrageous behavior.
In the apartment below lived Chris Robinson, a long-haired man with a luxuriant moustache and a storyteller’s soul, who later tended bar at the Afterdeck for 18 years.
Robinson’s tales of Thompson include a midnight boating mishap when the author fell out of his craft while trying to dock it. The vessel continued circling on its own, crashing into nearby boats and running amok in a local marina, with Thompson — convinced it was out to get him — paddling frantically away.
I too frequented the Afterdeck, soaking up the atmosphere and the stories with wide-eyed appreciation, both before and during my stint waitressing there. When (much to Phil Tenney’s secret relief) I quit to pursue my first writing job, that didn’t change.
Even today I wander over to the place with friends now and then, sitting on the wide wooden deck, recalling past escapades and gazing at the endless ocean.
Phil Tenney is gone now, but his influence remains in every meal served and every drink poured. Louie’s and the Afterdeck are ably spearheaded by Phil and Pat’s son Jed. And the cocktail waitresses, mercifully, are far more skilled than I ever was.
