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 - Rum Punching up Duval

Mark had a evening off work, so we jumped on the bikes and headed into Key West. The plan was to rum punch our way up Duval Street. Since booze on an empty stomach is never a good idea, we started at Kelly's Caribbean Bar, Grill and Brewery for Jerk Wings. These plump meaty wings are sweet yet have enough heat to keep you reaching for your cocktail.

Happy hour runs 4-7 and is always crowded. To get the specials, you have to be at the bar, so get there early. We arrived about 5 and were lucky to find two seats near the door. I ordered a rum punch and Mark immediately abandoned the plan and ordered a mojito.

This is a tricky drink to get right. Bartenders almost always blow it when it comes to the sugar mix. Too much and it's sickly sweet. Too little and all you taste is club soda. This one had a nice mix of lime and mint and leaned just a tad on the sweet side.

My rum punch was nearly perfect. For me, perfection is equal parts of dark rum, coconut rum, pineapple juice, orange juice and a splash of grenadine for color. No one part of the drink should stand out more than any other. Kelly's came pretty close to the mark with just a splash too much pineapple juice. It wasn't enough to knock the other ingredients out of balance though, so if we hadn't been moving on, I would have been quite happy to stay for a few more. Happy hour prices: well drinks 2.50 and one pound of wings, 4 bucks.

Kelly's has two claims to fame. The building is the original site of Pan Am Airlines, and Kelly is none other than Kelly McGillis of Witness and Top Gun fame.  She left Key West after a divorce and the bar is now owned by her ex-husband.  If you go, look for her Top Gun jacket in a small case above the bar. It's not well lit and out of eyesight, so it's easy to miss.

Back on the bikes, we pedaled south on Whitehead, to avoid the crush of tourists on Duval, and made our way to the Rum Bar. This intimate little place, on the ground floor of the Speakeasy Inn, has tables on the wraparound porch and enough seating inside for about a dozen.

Our favorite bartender, Bahama Bob had just gotten off work and we made a mental note to get here before 6 pm next time. Bahama Bob uses a secret recipe, perfected in Cuba, for the best mojito on the island.  The man is worth an entire blog post, so we'll come back to him later.

I grabbed a table for two, by the window, and Mark got the drinks. Still in a mojito mood, he took a chance. I stuck with rum punch.

The sweetness of the mojito was closer to where it should have been, but it suffered from an extra splash of club soda.  My drink must have been nearby when the bartender was mixing because some of that club soda, a non ingredient in rum punch, ended up in mine and it's not a tasty addition. Club soda cuts the flavor of the juice and turns the drink into an odd second cousin of the rum punch. It wasn't a disaster, mind you, I had no problem finishing it. It just wasn't a true rum punch. If there were happy hour price, these two drinks weren't included.

One more stop felt in order, so we continued south up Duval to the Southernmost Beach Cafe.

If you get here before sunset, this is the best place on the island to watch the orange ball drop below the horizon. A long pier stretches into the ocean offering a sensational view. The pier does fill up quickly, with lots of bulky tripods, so you need to be in place well before the sun goes down.

The satellite dish in the far distance is on the Naval station, the true southernmost point in Key West. If you're not military, you'll have to settle for a photo at the buoy, just around the corner from Southernmost Beach Cafe.

me at the buoy back in Jan of 2012

If you're not interested in the view, head straight to the bar. Specialty drinks, during happy hour, are just 3 bucks, so this place fills up fast. There was no room at the bar so we had to sit along the wall with a tiny shelf for a table. Mark stuck with mojitos and I went with a rum runner. (from the happy hour menu) It's basically a rum punch with blackberry and banana liquor. These bad boys are potent, so don't drink 3 and then try to get on your bike to ride home.

At this point, we forgot to take anymore pictures so just imagine one of the glasses from above. If you've seen one rum punch, you've seen them all. It's the taste that sets them apart.