A commoner drinks at Captain Tony’s Saloon, Key West, Fla.

If the Green Parrot Bar is my favorite Key West bar for chilling out and hiding among the locals, then Captain Tony’s Saloon must be my favorite bar on the island for getting a truly “only in Key West” experience.  There really is no other bar like Captain Tony’s I’ve ever encountered, and its uniqueness can be traced to its storied history, and an owner with a gloriously checkered past. 

Here are just a few historical reasons why Captain Tony’s Saloon is one of a kind: 

·         The first known building on this site was an icehouse that doubled as a morgue;

·         Even before the building’s morbid beginnings, it was the site of several hangings and burials;

·         In a later life as a telegraph station, it reported the news of the sinking of the battleship Maine, which started the Spanish-American War, across the world;

·         The site has also been used at various times as a bordello, a cigar factory and a speakeasy; 

·         After Prohibition, as Sloppy Joe’s Bar it supposedly became not just the first bar in Key West, but in the entire state of Florida;

·         Ernest Hemingway drank here – a lot – before Sloppy Joe’s moved down the street;

·         Since 1958, when a local charter boat captain named Tony Tarracino purchased the bar, it’s been known as Captain Tony’s Saloon.

Then there’s the legend of Captain Tony Tarracino himself.  To say he was larger than life is not an exaggeration.  With a history that included bootlegging, gambling, gunrunning and surviving a mob hit, his story would be fascinating even before he decided to become a bar owner.  But what a bar he inherited.

Tarracino would eventually become more famous for his saloon than for his other exploits, thanks in part to Jimmy Buffet, who honed much of his own persona playing gigs at Captain Tony’s Saloon in the early 1970s.  Buffet later immortalized Tarracino in his song “Last Mango In Paris.”   

It should also be noted that Tarracino even spent one term as Key West’s mayor.  Frankly, I can’t think of a better choice for the office.

I’m proud to say I met Captain Tony on my first visit to his bar way back in 2002.  He was sitting on a stool behind this gift shop greeting guests as they entered and exited.  He knew and remembered several of them personally.  The epitaph displayed on the wall is quite fitting and one I’m sure he would appreciate. 

So, let’s take a tour of the place, and you’ll immediately see how … ahem … deep-rooted the history of the bar and the character of its former owner are throughout Captain Tony’s Saloon.

Coming in to the left of the saloon’s large squarish bar, … there’s a huge tree inside the building.  A real tree that’s still alive.  More interestingly, it’s the original gallows tree from the days of hanging those found guilty of piracy.  The building, along with all the bras, business card, license plates and dollar bills, would come much later.   

Look under the tree for one of the grave markers still inside the bar.  Obviously, it’s not original to this place.  Rather, it was deposited here by a jealous husband who learned his wife frequented Captain Tony’s Saloon to rendezvous with her lover.  Or so the story goes.   

Toward the back of the bar is plenty more dark and dingy space for drinking, seemingly illuminated by Captain Tony’s mayoral campaign sign.  It’s appropriately weathered with age but then again so is everything else on the walls.    

Off to the side you’ll find the stage where bands play and, if you’re lucky, an occasional surprise celebrity passing through. 

Coming back counterclockwise around the bar, as the bra collection gets even more impressive, you’ll begin to see light breaking the darkness of the interior … if it’s daytime of course.  A game room is separated from the main bar area and provides pool and foosball as a distraction from drinking, whatever music may be playing and the inevitable people-watching.   

For me, the best place to absorb it all at Captain Tony’s Saloon is at the front of the bar near the entrance.  Order yourself a signature Pirate’s Punch – a wonderfully smooth and fruity rum concoction – and watch the insanity slowly unfold. After all, you’re only a few steps from Duval Street.   

And on this particular afternoon, we were lucky enough to have acoustic entertainment provided.  There are worse ways to spend a couple of hours in Key West than sitting in Captain Tony’s and sipping your cocktails to the rhythm of live music.   

Plus, you never know who you’ll wind up sitting with, or on.  Take a closer look at each bar stool, and you’ll find the name of a celebrity who’s been to Captain Tony’s Saloon before.  Full disclosure:  I took this picture for a female friend who is rather enamored by Sean Connery. 

There’s one more tradition at the bar that you should know about. According to legend, if you stand in front of the entrance and can flip a quarter into the fish’s mouth, you’ll have good luck for the rest of your time in Key West.  I don’t know if it works, but it is entertaining to watch so many people stop and try. 

Sloppy Joe’s has the name recognition.  The Green Parrot Bar has the local charm.  But Captain Tony’s Saloon is Key West in a nutshell.  And a lot of nuts can be found there.  Even if you’re not much for adult beverages, you owe it to yourself to check out Captain Tony’s Saloon when you come to Key West.