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Arts & Culture

In Key West's varied history, booze and bars are the throughline

A bartender raises a bottle in front of a bar full of sailors in Key West circa 1950.
Key West Art & Historical Society.
The inside of the Cabana Bar at 605 Duval Street circa 1950.

Sloppy Joe's on Duval Street became famous as Hemingway's hangout almost a century ago, in the 1930s. It turns out the island's history with booze and bars goes back even longer than that.

Cori Convertito is a curator at the Key West Art & Historical Society. She's researched the history of Key West bars, created an exhibit about them at the Society's Custom House Museum and recently gave an online talk titled, appropriately, "Happy Hour With The Historian."

WLRN asked Convertito how bars have shaped and changed with Key West's 200-year history.

CONVERTITO

Bars or saloons or grog shops — they've just been woven into the fabric of Key West since its founding in 1822. We're transient by nature. We always have been. I think we will continue to be as long as the tourist economy is here. And we're a port town. And I think that historically port towns have always been synonymous with sailors and drinking and Key West is really no exception to that.

WLRN

And at one point, there was a vote, right?

CONVERTITO

[In] 1907, the temperance movement was permeating the United States. There's a referendum that goes out, people are signing a petition and it gets on a ballot whether or not we should have saloons, or we should become dry here. It barely, barely passes us staying Wet versus us going Dry.

WLRN

And of course, Key West has been a Navy base from the beginning, but that really expanded during World War I, right?

CONVERTITO

The Naval Air Station Key West opens in 1917, and they're bringing down sailors for flight training so they can identify enemy submarines. They're young. They have money in their pockets, and they're looking for things to do. And one thing the Navy doesn't do is create recreational activities for them, these young men are turning to Duval Street, Caroline Street, to find entertainment and they usually find it in bars.

WLRN

And what was Prohibition like in the Keys? Rumrunning from Cuba seems like it would have been pretty easy.

CONVERTITO

We get Prohibition in 1919. [The] 1920s is a big Florida land boom. Unfortunately for Key West, that's not what's happening here. Our population is decreasing. Businesses are moving to the mainland because there's more space and it's less expensive. And so, during Prohibition, a lot of our locals turn to rumrunning almost because they have to. The Coast Guard's here, the Navy's here, and they're kind of turning a blind eye to it because they see that the locals are dependent upon it. They're not really causing a lot of problems. And we're too close to Cuba to sort of police it.

WLRN

And for a good chunk of the 20th century after World War II, this was a Navy town. What did that mean in terms of bar culture?

CONVERTITO

Our biggest population in Key West happens in the 1950s and 1960s, that post-World War II era. We have a lot of sailors. The Navy has a diverse population in terms of what their specialties are, and this is when you find that bars become very specific to certain sectors, like all the submariners are in [their] own bar, and the aviators are in another bar, and the shrimpers stick to themselves in a different bar.

WLRN

And when the Navy closed most of their facilities on the island in the early '70s, the town was broke, right?

CONVERTITO

Key West, to me, always finds a way to bounce back. Every time we're dealt this bad news economically, in particular, we find a way to regenerate. And that's what happens in the mid-70s. The Navy base closes in 1974,bBuildings are vacant. Businesses are vacant. And that allows for an opportunity for people from the mainland, particularly the gay population, moved down here. Property's cheap, we're kind of off the radar a little bit. We start getting dance clubs and things that kind of cater to that population, but they're open to everyone.

WLRN

Do you have a favorite bar?

CONVERTITO

You can always find me at the Green Parrot. I always know somebody in there. They always have great music playing. I think that is emblematic, to me, of that older Key West drinking culture — just come on in and grab a seat and you never know who you're going to sit next to.

Nancy Klingener was WLRN's Florida Keys reporter until July 2022.
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