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 my simple guide to drinking like Hemingway in Key West, you will too.

Hemingway look alike contest Sloppy Joes Key West

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). My good friend Mike from introduced me 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 Carl at Conch Republic Bikinis sent you and let him decide what you should drink. Of course they 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.  (I could tell a joke now about West Virginia but I know I’ll get a lot of hate mail.)  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

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, referred many matches here.

I 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 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.  As a point of fact, Nicholle Lottman our very first model, was named Playboys Sexiest Bartender of the Year 2010.  Just for some self-congratulation, I found her before they did!  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 Conch Republic Bikinis sticker behind the bar.

The Green Parrot

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 Conch Republic Bikinis stickers around town.  Stickers are kind of a guerilla marketing tool in Key West.  My buddy Mike, that’s him in the picture below, put me onto this.  Don’t be surprised to see a LOVE RUM? sticker and a Conch Republic Bikinis sticker side by side in most places in town.

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

Mile Marker 0 Key West

Mike from and me 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.

You will be drinking Papa Dobles here, Hemingway’s favorite drink.  Rum, lime, grapefruit and some drops of maraschino cherry juice.  Have an extra for me.

Inside Captain Tony's Saloon

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 Joes Bar Key West

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

A lot of Conchs and locals alike will call me out for taking you to this very touristy bar.  I can see their point but I do not agree.  I like this bar.  I like Bonnie who is always behind this bar. (Tell her hello for me).  I like to watch people who use too little sunscreen and drink too much beer come and go.  I 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 my favorite, a Cuba Libre.  Just make sure Bonnie uses quality rum.

Sloppy Joe's Bar

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 bar and courtyard setting and is home to the famous Homemade Bikini contest, an event near and dear to my heart. 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 Gulf of Mexico.  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.

Reviews 728x90

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 me @conch_bikinis so I 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 my last stop with you on this drinking tour, I 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.

Don’t forget to follow me at:



Nicholle Lottman Playboy Sexiest Bartender

Nicholle our first model and Playboy's Sexiest Bartender 2010. Southernmost point. ©2010 Conch Republic Bikinis


23 Responses to “How to Drink Like Hemingway in Key West”

  1. RumShopRyan April 21, 2011 at 5:12 pm #

    For whatever reason, it seems like the Green Parrot is always the last bar we end at. It’s open late, has great music and has a local vibe. Irish Kevin’s, Sloppy’s and Hogs Breath are staples, but the Green Parrot always seems the be the dessert of the night.

    Great story Carl!

    • Carl Grooms April 21, 2011 at 5:25 pm #

      Thanks Ryan. I agree, I tend to linger at the Parrot myself. I like the great choice of craft cold beer. Cheers. Looking forward to Buffett.

  2. Damon @ Let's Tiki April 22, 2011 at 3:01 pm #

    That sounds like a great tour. I haven’t been to Key West in a long time. I need to get down there!

    • Carl Grooms April 22, 2011 at 3:03 pm #

      If I’m in town I’ll do it with you. If not, you’ll have to send me live updates so I can laugh.

  3. Web Design April 23, 2011 at 9:51 pm #

    Hey, I read your blog post about How to Drink Like Hemingway in Key West | Coastlines & Tan Linesâ„¢ – thank you.

  4. Tucson Real Estate Pro April 24, 2011 at 1:52 am #

    Um, yes please! Great post, thank you!!!

  5. dogs April 24, 2011 at 6:43 pm #

    I would like to start my own blog one day. This was a really nice blog that you made here. Keep up the success

  6. mikerosss April 25, 2011 at 6:16 pm #

    found your site on today and really liked it.. i bookmarked it and will be back to check it out some more later

  7. Kate April 27, 2011 at 12:17 pm #

    This is AWESOME! Heading to Key West in late May and we are so going to do this one. Will report back!

    • Carl Grooms April 27, 2011 at 12:19 pm #

      Glad you enjoyed it Kate. Don’t forget to take the sticker challenge. Haha. If you are on twitter hit me @conch_bikinis so I can follow along :)

  8. Dave J July 21, 2011 at 1:51 am #

    Great Blog, I have followed the route several times (altho not always in that order and often adding in a few more stops) during the Fantasy Fest. Some how usually seem to forget what the rest of them were tho’……………Couldn’t be the rum could it ?????

    Last Mango in Paris. I JUST this week listened closely to the beginning of the song and now realize just WHO Jimmy was singing about. Sure hated to see that grand old letcher pass on. KW is a more than a bit less without him.

    • Carl Grooms
      Carl Grooms July 21, 2011 at 10:43 am #

      Dave thanks for the note. I kinda followed the route again last weekend. We’re doing a Key West Crawl on 17 September for a big group. If you are around or can make it . . . .

  9. Ivan Mccaffity August 17, 2012 at 4:18 pm #

    Omg! Superb posting, My wife and I appreciated the idea. Do you plan in advance to actually carry out a follow-up document? You actually need to come critique my webpage too! it is actually on the subject of website.

  10. Kendra Lamers August 17, 2012 at 11:25 pm #

    Omg! Awesome posting, My wife and I liked the idea. Do you intend to actually perform a follow-up blog? You ought to come examine my own rrnternet site as well! it is actually relating to website.

    • Shawn Martin
      Shawn Martin August 24, 2012 at 11:14 am #

      Perhaps one day, lol. We’ve done this so many times…

  11. Michael August 20, 2012 at 2:38 pm #

    My girlfriend and I just did this bar tour ourselves…my parents convinced us to go on a cruise with them (which I’m not a fan of) and I agreed only if it stopped in Key West…she had never been the crazy rock before so when we got off the ship at 8am I took her to the Southernmost Point, and then started our bar tour at 8:30…6 bars and $180 later I had to be dragged back onto the ship (mostly because I didn’t want to leave)!

    • Shawn Martin
      Shawn Martin August 24, 2012 at 11:13 am #

      So many people leave our little island in that state. Makes for some great stories though! Glad you had a good time.

  12. Bill January 31, 2013 at 12:55 pm #

    Was there 15 years ago, wish we had your info then. At the time I called the place THE LAND OF QUEERS, BUMS AND MIDDLE AGED COUPLES IN RENTED CONVERTIBLES. We’re going back mid Feb. with another couple and will follow your plan exactly. THANKS! (no convertible this time)

    • Shawn Martin
      Shawn Martin January 31, 2013 at 2:45 pm #

      Key West is certainly an interesting and diverse place; but that’s what makes it so magical! Send us some pics no Facebook of your Hemingway Crawl! And good luck!

  13. Bill January 31, 2013 at 3:24 pm #

    Since you know the place so well, I was wondering how well you know the accommodations. Right now we have reservations at the Merlin Guesthouse. Any thoughts or suggestions?

    • Shawn Martin
      Shawn Martin January 31, 2013 at 9:42 pm #

      No idea about the Merlin but you are right around the corner from the Rum Bar, and the southernmost point, you are a bit south of the busy part of Duval so that is good in my opinion. I like that area to stay personally if you don’t mind a walk to the Sloppy Joes end of the street.

      If you want to be closer to the action (but still off the path) try Angelina Guesthouse. My personal favorite. But, no small kids (if there are any coming).

      Hope you all have a great time! Tell Bob at Rum Bar Shawn from Coastlines says hi. Certainly try any rum he offers you, and he also makes a great mojito! Also, you must have one of his Painkillers!



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