I’m not going to deny it: When it comes to imbibing, Key West turned pro a long time ago.

There has long been a liquid history down at the end of A1A, with generations of pirates, wreckers, shrimpers, military, and other locals feeling somewhat justified in their little island being a bit cut off from the mainland to encourage a rollicking, hardworking, hard-drinking atmosphere. My first visit was as a high school student on a snorkeling trip in the ‘70s, and the wide-open attitude of “The Rock” enthralled a teenage boy. My adult self brought my wife, Cherri, to Key West and the Keys, and she fell in love with the place as much as I did. We vacationed there for decades and sipped our way through many pleasant days, as well as living in Key West for a few years before moving up to the Space Coast.

The Green Parrot, band playing

The Green Parrot

Photo Courtesy of the Green Parrot/Facebook

The hospitality industry grew over the decades with increased tourism thanks to ferries, the, and passenger air service. Prohibition only encouraged Key West citizens’ relationship with alcohol, both locally and as a stepping stone for thirsty Americans to liquid delights in Cuba. This was the scene when Ernest Hemingway stepped onto a Key West dock in 1928, and his next twelve years grew a blend of truth and legend still with us today.

I caught up with an old friend down in Key West, Jack Terry. He’s lived and worked for 14 years at Ocean Key Resort as well as the old Rum Barrel, where I used to perform rum tastings. He spent a year as Tommy Bahama’s national rumologist, and has published several works of fiction set in and around Key West. As I sipped one of Jack’s Papa Doble Daiquiris, Jack shared that “Customers always ask me, ‘Where and what did Hemingway really drink?’ As much legend and myth has grown up around Hemingway’s time in Key West, one of the few factual things known is where he drank, and those are the two places everybody knows.

The original Sloppy Joe’s, which is now Captain Tony’s Saloon, and the ‘newer’ Sloppy Joe’s—‘new’ being relative, seeing as how it opened there over 80 years ago. There probably were other places, but the population of Key West in the 1930s, when Hemingway lived there, was less than half of what it is today. Fewer people mean fewer bars, and most of those that were open then certainly didn’t survive.

Sloppy Joe’s, outdoor view, patrons enjoying

Sloppy Joe’s

Photo Courtesy of Sloppy Joe’s/Facebook

“Some other possible Hemingway watering holes exist, although one wasn’t a bar when he went there. One is Blue Heaven, and it’s where Papa would watch cockfights and referee boxing matches. Pepe’s Cafe has been open since 1909, although not at its current location. Next is the Green Parrot Bar; while not officially becoming a bar until after World War II, it was a Cuban grocery that also sold alcohol and had live music in a back room. Based on its proximity to his house and his penchant for exploring new cultures, I wouldn’t be surprised if Ernest spent time there, but sadly, there is no historical account of it, and he was known for using places he frequented as stand-ins for places in his writing.”

Pepe’s Cafe retro photo black and grey

Pepe’s Cafe

As far as what he drank, Hemingway was a notorious imbiber of many spirits. However, rum was—and is—the spirits of the Caribbean and New World tropics, and he embraced both the spirit and its own unique world. “Rum was—and remains—the drink, bar none, of the Caribbean, where my grandfather spent half his life,” said author John Hemingway, Ernest Hemingway’s grandson. “It was and always has been a drink of men, like Ernest Miller Hemingway, who loved the sea and fishing.” Just as locals do in the “little latitudes,” rum is best enjoyed with friends.

Tom Corcoran is a celebrated Florida-based crime novelist and Florida Keys historian. We spoke by phone while Tom was experiencing South Florida’s I-95 “Fury Road” driving experience, and he explained about “the Mob.” “Hemingway nurtured a gaggle of fellow imbibers, a mix of locals and visitors, who would join him in his rounds,” he told me. “He knew the value of corresponding with people in power and being photographed with movie stars, artists, and the glamorous wealthy. But he admired most those who faced great dangers, the soldiers and bullfighters; and those who did the grunt work, like laborers and fishermen. You get the feeling they were his favorite drinking companions.”

People came and went in the Mob, with his favorite Conch (Key West-born) bartender and friend Joe “Josie” Russell running herd while running his own bar, Sloppy Joe’s. Hemingway would put up the Mob in the old Overseas Hotel, and they’d hit the local places like Raoul’s Place, the Cabana Club at 1111 Duval Street, and of course Sloppy Joe’s, as well as heading to Cuba when the mood hit. It was in the rum bars of Havana and Santiago where Hemingway learned of Daiquiris and Mojitos, so he and Josie brought classic rum cocktails back with them. Sugar and other sweeteners were often reduced or eliminated due to Hemingway’s aversion of sugar, but the rum was always front and center.

“Ernest Hemingway’s love for the Caribbean and world travel ran deep, and at Papa’s Pilar, it has always been important to us to pay homage to that, sourcing our rums from places where Hemingway had some of his greatest adventures,” said Lindsey Kops Mundy, national brand director for Papa’s Pilar Rum.

“We are inspired daily by Papa’s adventurous spirit, his vehement need to be a part of the action, and his love of socializing over great drinks among friends.”

Philip Greene’s book To Have and Have Another is a delightful read about Hemingway, his life, and his favorite cocktails. The Hemingway Daiquiri was born at El Floridita bar in Havana. “By the mid-‘30s, the Floridita had no fewer than five variations of Daiquiri,” Greene says. “The 1937 Floridita menu lists a drink called the E. Henmiway Special, a misspelled homage to their newest, and most famous, regular.”

Hemingway Daiquiri, cocktail with garnish

Hemingway Daiquiri

Hemingway Daiquiri

From Papa’s Pilar Distillery


  • 1.5 oz. Papa’s Pilar Blonde Rum
  • .75 oz. Fresh Lime Juice
  • .5 oz. Fresh Grapefruit Juice
  • 1 tsp. Maraschino Liqueur
  • 1 tsp. Sugar (omit if you’re channeling your inner Hemingway)
  • Lime Wheel (for Garnish)

Preparation: Combine all ingredients in a shaker with ice and shake. Strain into a coupe glass. Garnish with a lime wheel.

Classic Daiquiri


  • 2 oz. White Rum
  • .75 oz. Lime Juice
  • .75 oz. Simple Syrup
  • Lime Wheel (for Garnish)

Preparation: In a shaker, combine all ingredients. Shake thoroughly and strain into a coupe glass. Garnish with a lime wheel.

Greene states that Papa’s favorite sipper was the Green Isaac’s Special, a cocktail that appears in Hemingway’s novel Islands in the Stream. “Where Thomas Hudson lay on the mattress his head was in the shade cast by the platform at the forward end of the flying bridge where the controls were and when Eddy came aft with the tall cold drink made of gin, lime juice, green coconut water, and chipped ice with just enough Angostura bitters to give it a rusty, rose color, he held the drink in the shadow so the ice would not melt while he looked out over the sea.”

Green Issac’s Special


  • 2 oz. London Dry Gin
  • 4 oz. Unsweetened Coconut Water
  • 1 oz. Lime Juice
  • 2-4 dashes Angostura Bitters
  • Lime Wedge or Peel (for Garnish)

Preparation: Add all the ingredients to a shaker and fill with ice. Shake and pour unstrained into a tall glass. Garnish with a lime wedge or peel.

As for the Papa Doble Daiquiri, in the well-researched James McLendon book, Papa: Hemingway in Key West, McLendon writes, “The Dobles (Daiquiri), by then a tourist attraction in Key West, were a mixture of two and a half jiggers of white Ron Bacardi rum, the juice of two fresh limes, the juice of a grapefruit half, capped off with six drops of maraschino (liqueur), all molded into one.”

Papa Doble Daiquiri


  • 2.5 oz. White Rum
  • Juice of Half a Grapefruit
  • 6 tsp. Maraschino Liqueur
  • Juice of 2 Limes
  • Lime Wedge or Peel (for Garnish)

Preparation: Add all the ingredients to a shaker and fill with ice. Shake and pour unstrained into a tall glass. Garnish with a lime wedge or peel.

Whether it’s your first time in Key West or you’re a repeat offender, consider spending an afternoon sipping your way through this selection of Papa Hemingway’s favorite rum concoctions. I might just see you there!