How to Drink Like Hemingway in Key West

March 15, 2017

How to Drink Like Hemingway in Key West

The non-definitive 7 bar, Hemingway inspired, historically inaccurate drinking tour of Key West.

There have been lots of famous people who have called Key West home.  Of all the big personalities that have walked her streets, drank in her bars and puked in her bushes, few have made the same impact as Ernest Hemingway.  Writing about Hemingway in Key West has already been done too many times. Instead we are going to follow in his wobbly footsteps as we drink. Hemingway took his drinking seriously and today if you follow our simple guide to drinking like Hemingway in Key West, you will too.


Annual Hemingway Look Alike Contest, Sloppy Joe's Bar - ©2010 Carlton Grooms


Rule #1 – We’re drinking the hard stuff.  You are permitted a beer from time to time if you are not up to task like the locals.  Honestly you really can’t be expected to keep up.

Rule #2 – Drink hard but not so hard you forget about all the fun you are having in Key West.  Don’t forget to eat. We like having you here but if you pass out, you stop spending money.

Rule #3 – We are starting at noon. It’s 5 o’clock somewhere but in Key West it’s always happy hour.  You have an hour at each stop.  Don’t worry too much about the clock but there is one bar where you must arrive at 3:30pm sharp.  Read on.

Bar #1 – The Rum Bar (1117 Duval). Our good friend Mike from introduced us to the bartender Bahama Bob.  He’s the real deal and the type of bartender Hemingway loved.  Don’t ask Bahama Bob for a fruity, sugary, touristy boat drink.  Don’t ask him for a drink at all.  Tell him you learned you are doing this crawl from Go2TheKeys and let him decide what you should drink. Of course it will all be rum.  Which brings us to the next rule.

Rule #4 – Key West is a rum town.  You should stick to rum on this drinking adventure.  The Keys have a colorful history with rum running during prohibition.  One of those rum runners was Raul Vasquez (1890-1957) who owned the property that is now the Rum Bar you are drinking at.  So be respectful.  Drink rum.

Bar #2Blue Heaven (729 Thomas St.) As you step back out into the sunshine head down Amelia St and hook a right onto Whitehead.  You will pass Hemingway’s house after three blocks.  If you see a cat with six toes don’t worry, that’s what happens when you inbreed. If you see a cat with seven toes, you’re getting behind on the alcohol power curve.  Take note and slow down a bit, you’ve got a great bar ahead of you.  After you pass Hemingway’s go one more block and take a left on Petronia St.  Blue Heaven will be at the next corner on the right.


Leah at Blue Heaven Bar - ©2010 Conch Republic Bikinis


A series of buildings set around a large outside courtyard Blue Heaven also has a tie to local lore.  The building used to be a brothel, gambling house, bar and even held cock fights and boxing matches.  Hemingway, an avid boxing fan, refereed many matches here.

We love to sit at the outside bar.  If you are a Kenny Chesney fan you’ll recognize it as the set for his video, “The Good Stuff”.  This is a great bar to be outside but still enjoy the shade.  Take a picture of yourself in the outdoor shower and have a try on the big swing.

Bar #3 – The Green Parrot (601 Whitehead) This bar has been around since 1890 and is right around the corner from Blue Heaven.  Head back up to Whitehead, take a left and it will be on the corner.

Playboy called The Green Parrot the definitive Key West Saloon.  Any magazine that can get hot women to pose naked for them must know a thing or two about bars as well.  What are you ordering here?  Rum of course, but I’ll give you a pass if you go for the beer because they have a great selection of craft drafts.  See if you can find the Go2TheKeys stickers around the bar.


Inside the Green Parrot. Great live music! ©2011 Carlton Grooms


Watch the clock while at The Green Parrot.  You’ll need to leave here at 3:15pm sharp to make your next stop!

Rule #5 – Look for the Go2TheKeys stickers around town.  Stickers are kind of a guerrilla marketing tool in Key West.  Our buddy Mike, that’s him in the picture below, put us onto this.  Don’t be surprised to see a LOVE RUM? sticker and a Go2TheKeys sticker side by side in most places in town.

Challenge #1 – Every hot girl who sends us a picture posing topless by a Go2TheKeys and LOVE RUM? sticker will get a free bikini from Conch Republic Bikinis.  No shit, serious.


Mike from and Carl practicing this tour. ©2011 Carlton Grooms


Bar #4 – Captain Tony’s Saloon (428 Green St.). This yellow building was the original Sloppy Joe’s and Hemingway drank here from 1933 to 1937.  So should you.  He arrived here at 3:30 every day, after a morning of writing in his pool house.  You should be arriving at that time as well.  As you leave The Green Parrot, stay on Whitehead and you will walk past the famous Mile Market 0 sign.  Stop and take a picture. Then stay on Whitehead until almost the end when you take a right on Greene.  It’s actually called Sunset Lane at that point but you’re probably already to drunk to read anyway.

Hemingway’s drink here was ...Rum.  Correct.  Try the rum punch and keep the glass, even the locals have a few in their kitchen.  Have an extra for us.


Inside Captain Tony's. ©2010 Carlton Grooms


Challenge #2 – Find the original words of Jimmy Buffett’s song, “Last Mango in Paris.” He wrote them on a wall so he wouldn’t forget the chorus running around in his head.

Bar #5 – Sloppy Joe’s Bar (201 Duval).  Guess who named this place? You got it, Hemingway.  He named it after a club in Cuba that was part bar and part seafood store. The floor was always nasty from the melting ice kept on the fish.  The patrons teased the owner Joe for having a sloppy place.


Sloppy Joe's Bar at night. ©2010 Carlton Grooms


A lot of Conchs and locals alike will call us out for taking you to this bar.  We can see their point but we do not agree.  We like this bar.  We like Bonnie who is always behind this bar. (Tell her hello for us).  We like to watch people who use too little sunscreen and drink too much beer come and go.  We like the live music. You can easily be led down the sugary pre-made rum drink path here.  Avoid the siren’s song of bad mixed drinks and order a simple Cuba Libre. 


Sloppy Joe's Bar ©2010 Carlton Grooms


Bar #6 – Hog’s Breath Saloon (400 Front St.).  Stumble back out onto Duval and head right.  Hog’s Breath is hidden one hundred yards down on the left, tucked in behind Ripley’s Believe it or Not.  This bar has a great outdoor setting and is home to the famous Homemade Bikini contest, an event near and dear to our hearts. It is held every October 28th during Fantasy Fest and draws huge crowds.  Some women plan their bikini all year, some pull together whatever they can muster on the spot.  All are a ton of fun. You might have to tack back to beer here as the next stop is going to be large.  Drink here until just before sunset and walk the straightest line you can to Mallory Square. Don’t fret you are less than 100 yards to the water.  Enjoy the fire eaters, comedians and dogs that take tips as the sun sets into the ocean.  Ahh, don’t you feel the calm.  The tingly sensation of feeling alive and enjoying the moment?  Yes?  Great.  Now it’s over, time to go drink some more.

Challenge #3 – The Hog’s Breath has a webcam right by the outside bar.  Your challenge is to make your own bikini and then send all your friends to the web address ( where you are modeling it.  Don’t forget to tweet us @Go2TheKeys so we can watch as well!

Bar #7 – El Meson De Pepe (410 Wall Street).  No not that Wall St. This place wasn’t around in Hemingway’s day but he’d like it if it were.  We’re stopping here to tip our hat to the days when Hemingway took his boat the Pilar across to Cuba.  Key West and Cuba have a lot of shared history.  In Hemingway’s day over half the residents were Cuban.

I’ve brought you to El Meson De Pepe for authentic Cuban food and to soak up some of that alcohol that is helping you make an ass of yourself.  Don’t forget to have a few Mojitos to wash that food down; here they are amongst the best in town.  When you are done eating, stay for the live music and dance some.  Don’t know salsa?  You just might after all that liquor you’re putting down your throat.

This is our last stop with you on this drinking tour, we hope you’ve kept up and have the energy to keep going.  Now that you know a little more about the town, go, be free, explore and make your own fun!

Challenge #4 – Dance the Salsa at El Meson de Pepe.

Rule#6 – Have fun, be safe, tip well and don’t drive in your current state.  Thanks for coming to Key West.


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