The bartender who invented a cocktail to get rid of extra rum...

...and accidentally created the most famous drink in the Florida Keys.

Author

Florida Keys Road Trip
June 23, 2026

The Rum Runner

THE FLORIDA KEYS ROAD TRIP NEWSLETTER

Hey Keys lovers! If you are reading this from somewhere that still requires a jacket, we have good news: the water is warming up, the winter winds are finally laying down, and the spring bird migration has officially arrived in the islands.

This week, we are looking at a bartender's happy accident that became a legendary cocktail, a Key West smuggler who had his own key to the county jail, and why you might want to rethink what goes into your beach bag before you cross the 18-Mile Stretch.

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❓ KEYS TRIVIA

What is the only city in the continental United States that has never recorded frost, ice, sleet, or snow?

Answer at the bottom of the newsletter.

📣 THE MILE MARKER ROUNDUP

🪸 Coral Bleaching Warning: NOAA has issued a coral bleaching warning for the Florida Keys — the second-earliest alert ever issued. The Florida Keys National Marine Sanctuary Advisory Council is prepping emergency backup strategies including deeper-water nurseries, shading systems, and inflatable floating canopies designed by University of Miami engineering students. https://keysweekly.com/42/sanctuary-advisory-council-preps-for-coral-bleaching-backups-welcomes-superintendent/

🇺🇸 America's 250th Celebration: Key West is hosting a major America 250 celebration at Truman Waterfront Park on Friday, June 27. The event features a parade, live music, food vendors, a military tribute, and fireworks as part of the nationwide semiquincentennial celebration. https://www.keywestchamber.org/

🎣 National Geographic Double Header: An Islamorada charter captain reported a once-in-a-career sailfish encounter at the Islamorada Hump this week. With the Gulf Stream sitting just 4-8 miles off the beach in 84°F water, they had a double hookup on sailfish, plus vermillion snapper, yelloweye, wahoo, and blackfin tuna all in the same session. https://keysweekly.com/42/florida-keys-fishing-report-a-national-geographic-double-header/

🇺🇸 Rare 1876 Centennial Flag: The Sloan Centennial Flag — a rare 12x18-foot 13-star flag from 1876 — will be on public display at the Alex Vega Firehouse Museum in Key West, July 2-4. It is one of only a handful of surviving flags from America's first centennial. https://keysweekly.com/

🎥 TimeFlies in Key West: Videographer Chris Sloan has released a 13-part time-lapse and drone video series covering every neighborhood of Key West — from underwater to aerial, from Fausto's Food Palace to the holiday parade. The project took 5 years and is dedicated to the memory of Cheryl and Crystal Cates. https://keysweekly.com/42/this-is-key-west-like-youve-never-seen-it-before/

🌴 THE SUMMER WATER TEMPERATURE GUIDE

June through September is actually the best time to get in the water in the Keys.

Water temps hit 84-85°F right now. Visibility is excellent. Snorkeling, paddleboarding, and kayaking are all at peak conditions. The Gulf Stream is sitting tight — just 4-8 miles off the beach. This is the time to book water activities, before August heat makes everything feel like a hot tub.

A Better Way to Plan Where You Stay in the Florida Keys

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🤿 THE RUM RUNNER COCKTAIL
How a bartender's surplus of rum accidentally created the most famous drink in the Florida Keys.

The Rum Runner was invented by John "Tiki John" Ebert at the Holiday Isle Tiki Bar in Islamorada in the early 1980s. Faced with an excess of rum and banana liqueur before a new shipment arrived, Ebert mixed what he had: Meyers rum, banana liqueur, blackberry brandy, and grenadine. He created what became the most famous cocktail in the Florida Keys.

The drink was named for the Prohibition-era rum runners who smuggled liquor from Cuba to the Keys in small boats through mangrove channels. The most famous was Raul Vasquez of Key West, who operated out of 1117 Duval Street — now the Speakeasy Inn.

The original Holiday Isle site has since been completely redeveloped into Three Waters Resort & Marina, a Marriott Tribute Portfolio property. You can still order a Rum Runner at the tiki bar on the same stretch of oceanfront where it was born. The Speakeasy Inn at 1117 Duval still has Raul's bottle-shaped balusters on the porch. The Rum Row Bar at the Gates Hotel is named for the line of ships that waited offshore during Prohibition.

🏴‍☠️ RAUL VASQUEZ — KEY WEST'S MOST BELOVED CRIMINAL

He advertised his illegal business on his front porch. The evidence is still there today.

Raul Vasquez was born in Tampa in 1890, moved to Key West as a child, and worked as a cigar selector at the Gato factory. When Prohibition hit in 1920, he pivoted to rum running — smuggling liquor from Cuba to Key West in small boats through the mangrove channels.

His first trip to Cuba was a disaster. He didn't know how to navigate. His compass pointed at the engine. He had to steer by the stars. His crew mutinied — he pulled a pistol. It took 5 days to reach Havana instead of one.

He carried gold coins instead of paper money. His reasoning: "If the Coast Guard got after him and he had to jump overboard and swim, it wouldn't matter if the coins got wet."

He advertised his illegal business openly — carving bottle-shaped balusters and playing card suit shapes into his porch railing at 1117 Duval Street. They are still there today. His bar, the "Florence Club," was named because several of his best customers had wives named Florence. When customers helped themselves while he was away, they'd write what they took on a marble slab. "No one ever stole a single bottle."

When jailed, he was given a duplicate key to the county jail so he could come and go without waking the jailer. He once supplied 150 suitcases of rum to a Shriners' convention in Key West.

The Speakeasy Inn at 1117 Duval Street still operates as a bed and breakfast. The bottle-shaped balusters are still on the porch. You can walk past them today.

✅ TRIVIA ANSWER

Key West.

The lowest temperature ever recorded there is 41°F on January 13, 1981. Weather records go back to 1871.

Until next week, keep your windows down and your watch off.
The Florida Keys Road Trip Team