The Most Interesting Bar in Key West

Your long distance, but faithful correspondent, Mark is back.  This post is a bit long but I think you'll understand.

With apologies to Sloppy Joe's and every other place near Duval Street, for pure character, I think Capt Tony's is the unquestioned leader of the pack. Where else do you get pirates, hangings, tombstones, Jimmy Buffet and Hemingway on one package?  It bills itself as the "Original Location of Sloppy Joe's" but it's way more than that.

It's easy to find.  It's a big yellow building just a half block west of Sloppy Joe's on Greene Street and barely off Duval.  There is a big ole Goliath Grouper out front as part of it's sign. Definitely hard to miss.  After you've had some Pirate Punch, go outside, stand with your back to the fish and try to throw a coin in it's mouth.

This building truly was the original location for Sloppy Joe's and where Hemingway spent much of his time from 1933-1937. But all good things must get screwed up. In 1937, in a dispute over the rent, Joe Russell moved his place just down the street to it's current location.  In 1958, this old bar was bought by a Key West icon, Tony Tarracino. He was a boat captain, gun runner and former Mayor.  Hence, the current name.  Tony ran for office on the platform that he intended to drink, gamble and chase women until the day he died.  He also declared himself the most honest politician in America.  He was elected.  Classic Key West.

When you first enter the door closest to Duval, you'll immediately notice a large tree growing through the floor.  Back in the day, it was deemed perfect for hanging pirates.

Unfortunately, when they began to construct the building, they found that dead pirates didn't get much of a burial.  They apparently dragged them a short distance away and dropped them in shallow graves.

Today, beneath the pool tables lie the remains of a whole bunch of them.  Don't worry, if you look around the base of the wall, you'll see the bottles of holy water that keep their spirits quiet. Go ahead and enjoy your game.

By now, you have certainly noticed that the ceiling is covered in signed bras, dollar bills and business cards.  If you want to add yours, just ask the bar tender for the staple gun.



 The bar stools are painted with the names of famous people who have sat on them and, in many cases, were frequent patrons.  The biggest names, are actually on stools now hanging from the pool room ceiling.

If you come in the door just a little farther east of Duval, there is, almost always, a singer playing guitar for the folks. On this day, it was a talented fellow named, Gary. That is exactly where Jimmy Buffet got his start.  As a matter of fact, if you go into the Men's Room, you can see where he penned the chorus to "Last Mango in Paris." I wonder what he was doing at the time?

Yes, Ladies, women go in there all the time.  Guys, if it's a late Friday or Saturday, they don't always knock.

If you thought this was enough, you are sooo wrong.  It's time to tell you about the two tombstones you'll find.  Over near the pool tables, there is a tombstone in the floor (hell, it's apart of the floor) that belongs to a girl named Elvira.

She once worked in the kitchen and was married to an older guy who drank wildly and elevated carousing and philandering to new heights, even while she was in back.  One day, she had enough and came out and slit his throat. Although they didn't see any recourse to hanging her (especially after she killed her kids, too), they liked her well enough to keep her close.  I guess, true friends are forever. Today, she haunts the place as "the Lady in Blue."

The second stone is at the base of the tree but no one is buried under it. (Didn't expect that, did you?) The stone belongs to an old girlfriend of Tony's. Supposedly, when she passed away, her husband found old love letters between her and Tony.  He got angry, ripped up the stone, drove it to Key West and threw it down outside the bar. He yelled in the door, "If you want her so bad, you can have her!"  Unfazed, Tony had the stone brought in and protected in case the husband changed his mind but he never came back.

Now, there is no way you will ever go to Key West and not visit Tony's, is there?

“All you need in this life is a tremendous sex drive and a great ego, brains don’t mean a shit,”  Capt Tony.

Happy Hour Series - Schooner Wharf

Anyone who's ever perched on a bar stool between 4 and 6:30 pm knows it's not just the drink that makes the hour happy. The bartender, the band, the view, and the company absolutely make or break a spot.

In the interest of science, and because we have nothing better to do with our afternoons, we've decided to hit every bar in Key West looking for that sweet mix that makes the perfect happy hour.

Okay, we've just discovered that over 360 places in Key West have liquor licenses so we're narrowing down our parameters to bars we find while wandering around the island.

Schooner Wharf kicks off the series with the earliest happy hour on the island - 7 am to Noon.  You read that right. 7 am.

Since they also serve a great breakfast, Mango Mimosas's are the perfect complement to any item on the menu.

Trust me, there's no better breakfast than one you wash down with a Mango Mimosa.







The music starts at 12 on most days and 6 days a week you'll hear Michael McCloud kick it off. While his dog, Cindy, hangs by his side, Michael will treat you to some outstanding folk tunes. His original music is currently played on five XM/Sirius channels. Be sure to listen for his song about an ex-waitress that he didn't like. It's hysterical. Also, be sure to give Cindy a scritch. She's a sweetie. In the evening, you may hear the Doerfels, a unique and talented family group that is great fun. Look for their guitars made out of old hockey sticks.

Look for us most weekdays around 9am.

 You can check out the place on their webcam


When you leave, be sure to head out along the waterfront. You are sure to see some huge Tarpon lolling around just below the surface or you might even be treated to a Manatee. Manatees are cool.

A Wilder Time at the Bull

If you're just looking for a drink, pretty much any door you step through in key west will lead you to a barstool. Even the donut shop has applied for a liquor license.  But if you want to dance your ass off and make some new friends while downing a few beers, head over to The Bull, on the corner of Duval and Caroline.

Every Tuesday, Wednesday and Thursday night starting at 8pm, Dawn Wilder energizes the crowd with an eclectic mix of oldies, rock, disco and classic country. She takes requests, knows a hell of a lot of songs and will ring a big red cow bell and shout thanks when you drop a bill in her tip jar. 

Something about Dawn's easy style and powerful pipes brings out the happy in the crowd. Everybody's singing along and the small dance floor is packed throughout the show.  Last Thursday, a couple of drunks jumped up on stage to harmonize and Miss Wilder was a good sport, sharing the mic for several songs before politely shooing them off stage when they got a little rowdy near the sound equipment. Since the Bouncer didn't look all that pleased, I'd recommend against trying to join the act when you visit. 

Make sure you stroll by The Bull, before going inside, someone will be out front offering 2 for 1 drink coupons.We're usually there on Thursdays, so say hello. We're the ones in the crowd singing the loudest.