The night Sloppy Joe's Bar disappeared...

...and why a $1 rent increase changed Key West history forever.

Author

Florida Keys Road Trip
July 21, 2026

The night Sloppy Joe's Bar disappeared...

...and why a $1 rent increase changed Key West history forever.

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Hey Keys lovers! If you've ever walked down Duval Street and heard the music pouring out of Sloppy Joe's, you might assume it's been sitting on that exact corner forever. But you'd be wrong.

This week, we're diving into the legendary night when Key West's most famous bar literally vanished down the street. Plus: the Tropic Cinema might have found a savior, the lobster mini-season is just days away, and we've got the incredible story of the woman who kept the Key West Lighthouse burning through 40 years of hurricanes.

❓ Keys Trivia

How did the city of Marathon in the Middle Keys get its name?

(Answer at the bottom of the newsletter)

📣 The Mile Marker Roundup

🎥 Tropic Cinema May Have a Savior

The Performing Arts Centers of Key West (the nonprofit behind the Tennessee Williams Theatre) has entered talks to take over operations of Key West's beloved Tropic Cinema, which closed its doors in late June.

🎸 Key West Celebrates 'Caffeine Carl'

The island lost beloved musician Carl "Caffeine Carl" Wagoner on July 9. The community honored him with a packed funeral mass and a vibrant Second Line Parade tribute down Duval Street.

🪸 Third Artificial Reef Deployed

Monroe County's grant-funded artificial reefs program just deployed its third reef off Key West in the Gulf, creating new habitats and enhancing recreational diving opportunities.

🌡️ Ocean Temps Surpass 2023

NOAA reports ocean temperatures around the Keys are already warmer than at this time during the record-breaking 2023 bleaching year. However, the Gulf Stream is flowing closer to the Keys, which may bring periodic cooling.

🦞 Lobster Mini-Season Set

The highly anticipated two-day spiny lobster sport season is set for July 29-30. Remember: the daily limit is six lobsters per person in Monroe County, and night diving is strictly prohibited.

Made In® Cookware, the cookware brand behind the world's best kitchens, just launched Cast Iron.  Every piece is fully built in the USA and will be the last cast iron you ever need to buy.

🌴Partner Spotlight

If you're planning to join the thousands of "bug hunters" descending on the Florida Keys for the two-day spiny lobster sport season on July 29-30, you need a game plan. For first-timers, the sheer number of boats on the water can be overwhelming, and the marine patrol will be out in full force checking coolers and measuring gauges.

That's why seasoned locals recommend getting your boat in the water by 5:00 AM. Pre-load all your gear the night before, double-check your saltwater fishing licenses, and make sure you have your measuring gauge attached to your wrist. In Monroe County, the limit is six lobsters per person, per day, and you must measure the carapace (which must be larger than 3 inches) while still in the water.

If you want to avoid the heaviest traffic, consider skipping the Upper Keys and heading down toward the Middle Keys. And remember: no spears or hooks are allowed—just a tickle stick, a net, and a lot of patience.

🧩 Deep Dive

Sloppy Joe's Bar: The Great Disappearing Act of 1937

It was dark the night Sloppy Joe's Bar disappeared. In the middle of the Great Depression, Key West was teetering on the brink of financial disaster. But even that didn't explain how a full-sized saloon could up and vanish in the middle of the night.

The story starts with Joe Russell, a Key West native, charter boat captain, and Ernest Hemingway's favorite fishing companion. On December 5, 1933—the day Prohibition was repealed—Russell opened a legal bar at 428 Greene Street. It was a doorless, run-down building with sawdust on the floor, pool tables, and 10-cent shots of gin. Hemingway, a regular, suggested the name "Sloppy Joe's," borrowing it from a Havana club where melted ice always made the floor wet.

For three and a half years, the bar thrived. But in 1937, Russell's landlord, Isaac Wolkowsky, decided to raise the rent from $3 a week to a whopping $4 a week. Russell was furious. He quietly purchased the former Victoria Restaurant at the corner of Duval and Greene Streets for $2,500. There was just one problem: a clause in his lease prohibited him from removing any furnishings from the building.

Russell waited until Wolkowsky left town on a business trip. On the night of May 5, 1937, Russell's lease officially expired. He recruited a "midnight mob" of his most loyal drinkers, and together, they picked up every single piece of furniture, every bottle, and every fixture, carrying the entire bar down the street to its new location. The bar never actually closed during the move—customers simply picked up their drinks and walked. Service resumed at 201 Duval Street with free drinks for the rest of the night.

When Hemingway, who was in Spain at the time, heard about the midnight heist, his response was simple: "Only in Key West."

Have you ever closed down Sloppy Joe's? Hit reply and tell us your best Duval Street story.

🕰️ Lore & Legends

Barbara Mabrity: The Woman Who Kept Key West's Light for 40 Years

In 1826, Barbara Mabrity and her husband Michael were assigned as the keepers of the Key West Lighthouse. It was a grueling, isolated job, but they managed it together until 1832, when Michael died of yellow fever. In an era when it was nearly unheard of for a woman to hold such a position, Barbara took over as head keeper.

For the next four decades, she kept the light burning. She survived the devastating hurricane of 1846, which completely destroyed the original lighthouse and tragically claimed the lives of six of her family members who had sought shelter inside. When the new, taller lighthouse opened in 1848, Barbara was right back at the top, tending the flame.

She guarded the light through multiple killer hurricanes, the outbreak of the Civil War, and decades of isolation. Today, she is remembered as one of the longest-serving female lighthouse keepers in American history, and a U.S. Coast Guard cutter (WLM 559) bears her name. You can still climb the 88 steps of her lighthouse today—and most people do it without ever knowing the incredible woman who kept it shining.

✅ Trivia Answer

Railroad workers building Henry Flagler's Overseas Railway found the grueling, unrelenting labor so exhausting they complained it was "getting to be a real marathon." The name stuck for the local railway station, and eventually, the entire city.

Bonus fact: The Seven Mile Bridge, which connects Marathon to the Lower Keys, was the longest bridge in the world when it was completed in 1912.

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

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