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.

Little Room Jazz Bar

When sensory overload hits, and you need to decompress, head south to 821 Duval and the smoothest spot on the island -  The Little Room Jazz Bar. A recent discovery for me, and a spot I can't wait to get back to. 

Step inside and take a moment to let your eyes adjust to the dim light. Saxophones, Violins and Mandolins adorn the rich maroon walls. Candles light the dark wood high top tables and a flat screen running footage of sharks and other fishes creates a relaxing backdrop behind a portion of the bar. 

Though performers aren't on an elevated stage, the main seating area offers plenty of room for jazz lovers and two side rooms feature stuffed chairs and a couch for a more comfortable listening experience. 

Live jazz starts at 8pm nightly and the club offers two daily happy hours. 2-8pm and 12:30am to 2:30am. Don't ask for a well drink though. The Little Room's offerings are limited to craft beers and wine. For my party, that worked just fine. My son grabbed a glass of white wine and my friend James and I downed a couple of beers. (James and I are pictured below)

You can check their website, for a list of daily performers, though I'm not sure it's current. We were there this past Tuesday and what we heard didn't sound anything like the Haitian infused Jazz I was expecting. Whomever it was, entertained the crowd with a couple of sets that mellowed us enough to continue our crawl up Duval.


Update:  I should have actually read the white board I wandered past at the front door - a duo called, The French Connection was the featured act that night. 

"Here a cluck, there a cluck everywhere a cluck, cluck"

Mark here. It's time for a chicken post. I had to do it.  It was a gimme.

A quick explanation for those who haven't been here yet,  Key West is loaded with feral chickens. They populate every silly part of this island.  Even after I've told you, you'll still be amazed and amused by them. They're descended from released fighting cocks and escaped domestic birds and now roam freely.

They're beautiful critters and they certainly add charm and color to the town.  No doubt about it.  I am certain tourists take more pictures of chickens than Hemingway's House. On the whole, they are pretty cooperative models and their vibrant colors seem to naturally complement the tropical flowers.

They definitely seem to enjoy the lifestyle.  On any given day, you can find chickens hanging out at the beach...

...or just lounging in the sun.

That's not to say they are all freeloaders.  This fellow seems very good at waiting tables.  That said, I suspect he would have stolen your order when it arrived. Not a good way to keep your job.

Others seem satisfied with simpler jobs like cleaning "floors" at outdoor restaurants.  I guess it's important to find the job that suits you best. It's honest work, after all.


Now for the downside, those devils don't just crow at dawn. I've heard them bellowing at 3am like drunken college kids.  The locals often find them pretty annoying.

I suppose when it comes to Key West's chickens,  the best approach is to just take them for who they are, a charming addition to the landscape.  If Key West stands for anything, it's "live and let live." Then drink a Rum Punch.

Restaurants - Blue Heaven

One of the most popular breakfast options in Key West, you'll find Blue Heaven tucked in Bahama Village, at the corner of Petronia and Thomas, just a short walk from Duval Street. The main seating area is outside under the Spanish Lime trees. Free range, err, roaming chickens and roosters wander through the tables most days, looking for handouts. (just not this day)

The food is excellent but a bit on the expensive side. Mark and I headed here spur of the moment a few days ago in desperate need of breakfast. By the time we got our food, we were so hungry we forgot to take pictures, sorry. You'll have to believe me when I say it was as beautiful as it was tasty. I gorged myself on the airy blueberry pancakes and was squirted in the eye by more than one gigantic blueberry my forked pierced.  Mark had a fluffy ham and cheese omelette and could barely finish it. Their specialties are a variety of Eggs Benedict dishes including a Lobster Benedict, ordered by a guy at the table next to us. I really wanted to ask for a bite.

If you're used to a breakfast that includes the staples - bacon, toast, fruit, you're out of luck. Everything here, is á la cart, so costs add up quickly.  Mark and I stuck with the basics, his omelette, my 2 pancakes, a coke and an ice tea and the bill, with tip, was 27.84. If you're not on a tight budget, I'd say go. Otherwise, you'll get just as good a meal, for a bit less, at Two Friends Patio, and they don't hit you with the á la cart thing. 

If you have to wait on a table, as we did, you can pass the time at the ping pong table. 

This is Jesk, one of the resident cats. On the Blue Heaven website, they were offering her up for adoption in 2007. I guess it didn't take. 

Mark and I killed time at the bar, while we waited for a table. 

Key West Custom House: Art and History Museum

Mark here.  Want to hear about a place we should have checked out a long time ago? The Custom House, on the northwest corner of Key West, near Mallory Square, is definitely one of the most striking buildings on the island.  The 3-story, red brick structure is gorgeous and it's entrance is graced by a 40-foot sculpture of two ballroom dancers. Inside, it houses the Key West Art and History Museum.

Either before or after you go inside, take the time to walk around the outside of the building. The grounds are gleefully populated with a bunch of marvelous sculptures of people enjoying life.  The artist, Seward Johnson did a terrific job of capturing folks enjoying simple pleasures and some more formal or exotic ones, as well.  Many of the statures are positively lifelike. I'm not going to post pictures of the statues. I want you to have the full delight of seeing each one fresh.

The historical exhibits focus on the early days of Key West and the building of the Overseas Railroad. Building that railroad was a fantastic engineering feat and they have several displays that really show just how fantastic. They also have several great displays illustrating what life was like in the Lower Keys during the days of Hemingway and earlier. I think a lot of us are closet history buffs so I think that stuff is cool.

They also have several exhibits of artwork from local artists and, hands down, my favorite exhibits are the bas relief wood sculptures by Mario Sanchez.

He was the son of a cigar maker and a local folk artist who depicted everyday life on the island.  He worked outside under a tree using simple wood chisels and dime store brushes. For me, that adds to it's charm. I love their light-hearted tone and simplicity.

Mario based many of his characters on actual local folks and the museum does a nice job of sharing some of the back stories of the people in the works. If you look carefully, you'll notice many of these people as recurring subjects. You may also notice that the atmosphere of tolerance and acceptance in Key West goes back at least 100 years.  It's evident in many of his pieces.

We waited over a year to visit the Custom House but, once we got there, I was delighted. It's definitely worth the time.

Captions for a Rainy Day

Me at the recent Star Trek Into Darkness showing. 

If you're a hearing impaired resident or visitor to Key West and want to catch a movie, you're in luck! The local Regal Theater behind the Wendy's off Roosevelt on the north side of the island, has closed caption glasses. All you have to do is ask for them at the box office, when you buy your ticket. If you don't have a Regal Rewards card, they will ask you to sign a checkout form.

The glasses are easy to use. The manager will set them to the correct channel (theater number) and all you have to do is hang the receiver around your neck and put on the glasses. Sometimes, the cord for the receiver won't be attached to the holders on back, if it's not, just slide the cord under the clips and you're good to go. 

Captions are a light green and appear to float in the air in front of you. If you move your head, the captions move with you. A nice plus, if you have to reach for the popcorn. 

You can adjust where the captions appear by holding onto the black piece on the side of the glasses and clicking it up or down. 

If you're watching a film that's longer than 90 minutes, the top of your ears will get a little sore. I slide the glasses on so that some of my hair is over my ears and that helps. 

Some caption glasses out there are also for the visually impaired and they will describe the action on the screen. I am not sure if these glasses have that ability, but I did have one manager ask if I needed the audio turned on, so they probably do.  You can check with the theater, before you go, if you have any questions. 

Regal Theater 3338 N. Roosevelt Blvd, Key West, FL - (305) 294-0000

Happy Hour - Alonzo's Oyster Bar

I can't count the number of times we've walked past A& B Lobster House and Alonzo's Oyster Bar, on our way to someplace else. In the last year, Mark had suggested dinner a few times, but the word Lobster always made me leery of prices.  And then, a couple of days ago, he pointed out that the two were separate entities and suggested happy hour at Alonzo's.  Oh yeah. There's that word bar at the end of the sign.


Alonzo's is located in a great spot, on a corner of the pier in the Key West Bight,  next to where they feed the Tarpon everyday at 4 pm.  If you've never watched a swarm of Tarpon (many topping 150 pounds), fight over super sized chunks of fish, you're missing one of the best shows in Key West. Occasionally, you'll spot a Nurse Shark or Manatee gliding through the scene. Feeding starts promptly at 4, so arrive 10-15 minutes early for a good spot. After the show's done, at about 10 minutes after 4, turn around and hit Alonzo's.

There wasn't room at the bar, so we asked if we could get a table for happy hour. Some bars in Key West won't honor the happy hour menu unless you're at the bar, so it's always good to check. Alonzo's didn't mind and we were seated at an inside table after about a ten minute wait.





Happy hour is from 4pm - 630pm daily with all appetizers and drink specials half price. Mark went with a mojito, his favorite, and I jumped onto a key lime martini.  The mojito wasn't as perfect as Bahama Bob's mojito over at the Rum Bar, but he thought it was pretty darn good.  My key lime martini was the best, by far, that I've had on the island. It was sweet and creamy with the traditional graham cracker rim. Some places skip the graham cracker rim which violates all sorts of happy hour rules and thusly nullifies their ability to call their monstrosity a key lime martini.

More importantly, it's a direct violation of the Key West By-Laws,

Rule 4, sec 4,

For a drink to be declared a "Key Lime Martini", said drink must have graham cracker crumbs around the rim.  A drink without graham cracker crumbs, can, however, call itself a Lime Martini but must omit the term "Key" from the name.  

Just like every sports bar in the world has buffalo wings, every eating spot in Key West has their own versions of fish dip and ceviche.  Since we're fans of both, we had to order one of each and neither disappointed. The fish dip was on the mild side, light on the spices, and topped with capers and chunks of red peppers. It was served with 3 different type of crackers. The ceviche was a excellent with onions and peppers with the conch meat, giving it a decent kick. Still hungry, we ordered the fish fingers and were a bit disappointed. They were okay, as far as fish fingers go, but the sauce was basic tartar and there was really nothing that stood out about the dish.

In the end, my fears of an expensive bill were unfounded. We ordered two specialty drinks, two sodas, three appetizers and the bill was only $30.  On our next visit, I'll request an outside table for some people watching. A true spectator sport here in Key West.