Today, we’re putting a Key West twist on cocktail hour and talking about the stories behind some iconic drinks that have quenched thirsts and sparked conversations for decades. Spoiler alert: You’ll want to try all of these at least once (or twice, if the first round went down too fast).
1. The Rum Runner
Origin:
Born in the 1950s at the Holiday Isle Tiki Bar in Islamorada (just up the road from Key West in the Florida Keys), the Rum Runner was a solution to a real problem. Picture this: A tiki bar overflowing with rum and liqueurs they needed to use up before the next shipment arrived. Voilà! A cocktail was born. It’s also named after the notorious rum smuggling days during Prohibition, when the Florida Keys were the go-to highway for booze smugglers coming from the Caribbean.
Ingredients:
- Light and dark rum
- Banana liqueur
- Blackberry liqueur
- Orange juice
- Pineapple juice
- Grenadine
Key West Connection:
Rum smuggling gave this cocktail its name and its legacy. During Prohibition, the area’s proximity to the Caribbean made it a hotspot for rum runners sneaking in illicit stockpile. Now, you can sip on this fruit-forward drink at iconic local joints like The Speakeasy Rum Bar while whispering, “This one’s for the smugglers.”
2. Key Lime Pie Martini
Origin:
Yes, this boozy masterpiece was inspired by Key West’s pride and joy, the Key Lime Pie. We don’t know exactly who decided to turn a dessert into a martini (New York and Florida still argue about this one), but honestly, we owe them everything.
Ingredients:
- Vanilla vodka
- Key lime juice
- Cream (or sweetened condensed milk for the overachievers)
- Graham cracker rim (extra points for presentation!)
Key West Connection:
The pie it’s based on was created in Key West way back in the 1890s using local key limes and sweetened condensed milk. Today, the Key Lime Pie Martini is a liquid tribute to this culinary classic. Try it at Lazy Dog or whip one up at home and prepare for a citrusy, creamy chef’s kiss.
3. Mojito
Origin:
Ah, the mojito. Straight out of Havana, Cuba! This refreshing drink dates back to the 16th century when it was apparently used to prevent scurvy and dysentery. Who wouldn’t want to fight disease with rum and mint? It evolved from a drink known as “El Draque,” honoring Sir Francis Drake.
Ingredients:
- White rum
- Fresh lime juice
- Mint leaves
- Sugar
- Soda water
Key West Connection:
Because Key West is just 90 miles from Cuba, you’ll find Cuban culture woven into the island’s food and drinks. Mojitos are served at just about every bar on the island, from First Legal Rum Distillery to Sloppy Joe’s, where you can sip one and feel like Hemingway himself.
4. Piña Colada
Origin:
Cue the tropical vibes. The Piña Colada was born in Puerto Rico. Both the Caribe Hilton (shoutout to bartender Ramón “Monchito” Marrero in 1954) and Barrachina Restaurant (1963) claim to have invented it, and honestly, they can both take credit because this cocktail is fabulous enough for two backstories.
Ingredients:
- White rum
- Coconut cream
- Pineapple juice
- Blended with ice (don’t skimp on that frothy texture)
Fun Fact:
The Piña Colada became Puerto Rico’s official national drink in 1978. It doesn’t technically have a Key West origin, but it’s pretty much the mascot of tropical island vacations everywhere, including this one. Don’t leave the island without trying one by the beach.
5. Mai Tai
Origin:
The Mai Tai hails from 1940s California, thanks to Victor J. “Trader Vic” Bergeron, who coined it from the Tahitian word “maita’i,” meaning “good” or “excellence.” This cocktail became the darling of the Tiki cocktail movement during the 1950s and gained popularity throughout the tropics.
Ingredients:
- Aged rum
- Lime juice
- Orgeat (almond syrup)
- Orange curaçao
Key West Connection:
While the Mai Tai isn’t Key West-born, its tropical flavors make it at home here. Imagine sipping one as you watch the sunset over Mallory Square. It doesn’t get more iconic than that.
Sip, Stroll, Repeat
There you have it, folks. Five iconic cocktails with stories as rich as their flavors. Next time you’re stumbling down Duval Street (safely, of course), order a drink with some history behind it and impress your friends with your cocktail knowledge.
Check out all of our suggestions on where to drink here!
If you’re feeling ambitious, try mixing these classics at home, but don’t skimp on the rum (it’s what Papa Hemingway would’ve wanted). And if you really want to level up your Key West adventure, subscribe to our newsletter and get all the insider tips on where to find the best happy hours, secret bars, and even more history-soaked sips.
Now, tell me… which drink are you trying first? Cheers to history in a glass!
