The Rum-Soaked History Of Key West’s Most Famous Cocktail

This bold, fruity cocktail has deep Florida roots.

On the southernmost edge of Florida—and just 100 miles from Havana, Cuba—is Key West, an island community beloved for its relaxed vibes, bohemian history, and top-notch barhopping scene. Key West bars take several cues from their not-so-distant neighbors in the Caribbean when building their cocktail menus; you’ll find plenty of fresh juices, drinks meant to be served frozen or on the rocks, and a heavy focus on rum.

In fact, all of these characteristics combine brilliantly to create Key West’s most famous libation: the Rum Runner. The skilled bartenders and bar owners of Key West know this fruit-forward beverage better than anyone else in the world, so when we asked them to break it down and explain why the Rum Runner has such a close association with the Conch Republic, they had plenty of wisdom to share. 

Related: The 26 Best Things To Do In Key West, Florida

What Is A Rum Runner?

While the exact origin story of the Rum Runner remains somewhat mysterious, legend has it that the drink was invented about eighty miles up the Keys in Islamorada in the 1970s. Legend holds the head bartender at the Holiday Isle Tiki Bar (now known as the Postcard Inn) found himself with a surplus of rum and a somewhat chaotic liqueur collection. In an attempt to make the most of what he had to work with, “Tiki John” Ebert combined rum, banana liqueur, brandy, and grenadine, and the resulting tropical sipper became known as the Rum Runner.

In terms of historical context, “the Rum Runner cocktail was born post-Prohibition, but early enough in the tiki craze [for folks] to remember the lore of rum-running throughout the Caribbean and Florida Keys after the Volstead Act was implemented,” says Tim Rabior, co-owner of General Horseplay and Tiki House in Key West. 

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How The Rum Runner Came To Key West

As we mentioned, Islamorada and Key West aren’t very far apart, and the whimsy of the Rum Runner had an easy time moving its way down the island chain to the farthest-from-shore Florida Key. Key West bartenders were eager to embrace a cocktail called the Rum Runner largely because Key West—thanks to its close proximity to both Cuba and the Bahamas—counted among the most valuable booze-smuggling spots during Prohibition.

“Rum runner” was the unofficial title given to individuals who took it upon themselves to collect spirits from the Caribbean and bring them ashore in Key West, where they could later be secreted to the mainland. In fact, several classic Key West bars were founded by these spirited outlaws.

Suzanne Humphries, food and beverage director of Sloppy Joe’s, tells us that Joe Russell, “the original owner” (who was also a close friend and fishing companion of Ernest Hemingway’s) “was a rum runner during Prohibition.”

Why Is The Rum Runner So Important To Key West Cocktail Culture?

After its birth in Islamorada, “the Rum Runner immediately took off and would cement the Florida Keys in cocktail history, enjoyed by locals and tourists alike. [In] Key West, it’s on menus at almost every bar on Duval Street [Key West’s main drag for nightlife],” Rabior says.

Not only does the Rum Runner blend bright fruit flavors with rum, but it’s also a non-pretentious drink that plays to Key West’s greatest strengths as a tourism attraction. According to Raymond Vazquez, owner of the Speakeasy Inn & Rum Bar in Key West, island bars appreciate cocktail creativity, but they also have a very soft spot for long-standing classics.

“[Key West drinkers] like having a drink out of a plastic cup. They don’t need tiki glasses and fancy stuff like that. They’re not looking for that when they come down here,” Vazquez says. A rum drink that goes down easily and reflects the tropical surroundings sums up what Key Westers want, and Vazquez appreciates the Rum Runner’s ability to show off quality Caribbean rum in an approachable way.

Of course, that doesn’t mean that some enterprising bartenders aren’t willing to play around with the standard Rum Runner formula and find ways to modernize this old-school favorite.

“While you may see Rum Runners all over Key West, nine times out of 10, they’re from a frozen machine and made with a frozen drink company’s pre-made mix, which we all know usually tastes artificial and is a sugar bomb, as those machines work based on sugar content)” Rabior insists.

However, he tells us that “at General Horseplay, we do occasionally make this cocktail, but with better and fresh ingredients. You’ll get premium rums and liqueurs, and fresh juices.” Rabior also says that while the Rum Runner is frequently served frozen in Key West, he prefers to serve the drink “on the rocks so you can skip the traumatic brain freeze.”

Where To Find The Best Rum Runners In Key West

It’s hard to go to a Duval Street bar without spotting a Rum Runner on the menu, but a few Key West venues particularly excel at this local standard:

Sloppy Joe’s

Hemingway’s regular haunt remains a Key West icon, and because they claim to be the first Key West bar to serve the Rum Runner, Sloppy Joe’s is a non-negotiable stop for anyone hoping to experience this drink in its purest form. Humphries says that Sloppy Joe’s serves its Rum Runners either frozen or on the rocks, and the drink contains “Bacardi Light Rum, blackberry brandy, crème de banana schnapps, sour mix, pineapple juice, a splash of grenadine, and a cherry garnish.” Enjoy it at the bar (as Hemingway would have done), or take it to go.

Speakeasy Inn & Rum Bar

The very accurately-named Rum Bar on Duval Street can be found on the ground floor of a charming historic building. The house contains an inn founded by cigar selector and rum runner Raul Vazquez, and that rum-running heritage contributes to the Rum Bar’s commitment to sugarcane spirits. The Rum Bar’s impeccable Rum Runner includes both white rum and premium dark rum, which lends extra depth of flavor to the banana and blackberry liqueurs, grenadine, and zippy orange and pineapple juices. 

General Horseplay

General Horseplay sometimes offers a Rum Runner as a special or an off-menu “if you know, you know” option, and in addition to using high-quality rums and freshly-squeezed juices, Rabior opts for “premium liqueurs from Giffard or Tempus Fugit” to elevate the cocktail’s flavor profile. He also likes to serve the drink “in a tiki glass or mug and garnish with a brûléed banana wheel skewed with a blackberry on top, a couple of pineapple fronds down the side, and a fun crazy straw.”

Southernmost Beach Cafe

If you want your Rum Runner accompanied by an ocean view, Southernmost Beach Cafe will set you up nicely. This waterfront restaurant and bar serves a refreshing frozen Rum Runner with punchy banana and blackberry notes, and the Bacardi Black floater on top gives it an extra potent kick. Should you need a snack to soak up some of that rum, order a plate of crisp and tender conch fritters with garlic saffron aioli.

Read the original article on Southern Living