Sloppy Joe’s, Duval Street Webcam

Once the sun drops behind Mallory Square, the crowd drifts a couple of blocks along Duval Street, and a good share of it ends up at the corner of Duval and Greene, outside Sloppy Joe’s. The Sloppy Joe’s webcam streams that corner live from 201 Duval Street in Key West, Florida, with the bar’s stage, the open windows and the busiest stretch of Duval Street in the same picture. It leads our Key West live cams, and it is the quickest way to see whether the stage is busy right now.

The bar has been on this corner since May 5, 1937. Joe Russell, a rumrunner and charter fishing captain, first opened it on December 5, 1933, the day Prohibition ended, in a rented building nearby on Greene Street that he leased for $3 a week. When he moved, customers carried their drinks and the furniture down the block so service never stopped, into a 1917 building that Russell bought for $2,500 and fitted with the longest bar in town.

Afternoons on the Duval Street webcam

Daytime on the live cam belongs to people walking Duval Street, which runs just over 1.25 miles across the island, from the Gulf of Mexico to the Atlantic Ocean. It is named after William Pope Duval, Florida’s first territorial governor, and in 2012 the American Planning Association listed it among its Great Streets. Six blocks of it were added to the National Register of Historic Places in 1971, which is why the wooden balconies and two-story storefronts around Sloppy Joe’s look the way they do.

The bar’s open sides make it easy to read the room from the camera. A half-empty floor at midafternoon means you can walk in; a crowd spilling onto the Greene Street sidewalk means the band has started and it will stay that way. That stage is why Sloppy Joe’s heads our live bar cams.

Sunset, then Duval Street at night

The evening rhythm in Key West starts a few blocks north. The Mallory Square cam shows the sunset celebration on the waterfront, with street performers and the cruise ship harbor, and that crowd walks south afterward. By the time it reaches this corner, the Sloppy Joe’s live cam shows Duval Street at its fullest, with groups on the nightly Duval pub crawl moving between Sloppy Joe’s, the original Margaritaville, Rick’s Cafe and the other bars along the strip.

Just around the corner on Greene Street, the building where the bar started is now Captain Tony’s Saloon, and a block or two away the Hog’s Breath Saloon cam covers another of Key West’s open-air bars from three angles.

Hemingway and the bar on camera

The name itself is part of the story. The bar on Greene Street opened as the Blind Pig, became the Silver Slipper once a dance floor went in, and, as local legend has it, took the name Sloppy Joe’s at Hemingway’s suggestion, after a loosely run bar he knew in Havana. Ernest Hemingway spent most of his evenings at the original Sloppy Joe’s between 1933 and 1937, and the bar has leaned on that connection ever since. Every July, during Hemingway Days, it hosts the Hemingway Look-Alike Contest, and the stage on the webcam fills with white-bearded men in fishermen’s sweaters. The 45th edition, in July 2026, drew more than 60 contestants, with the final round on Saturday, July 25, during a six-day festival that also marked the 127th anniversary of Hemingway’s July 21 birthday.

The current owners have run the bar since September 8, 1978, and Sloppy Joe’s celebrated 85 years at this corner on May 5, 2022. A few blocks south, Duval Street passes the San Carlos Institute, founded by Cuban exiles in 1871, and ends near the Southernmost House, a Victorian mansion from 1896 close to the buoy that marks the southernmost point of the continental United States.

Fantasy Fest on the Sloppy Joe’s live cam

The biggest crowd of the year comes in October. Fantasy Fest, started by local business owners in 1979, runs for ten days of costume parties, street fairs and parades; the Florida Keys tourism office lists the 2026 festival from October 16 to 25. The closing Fantasy Fest Parade rolls down Duval Street on Saturday, October 24, and the Sloppy Joe’s webcam, on the corner of Duval and Greene, is one of the easiest ways to watch it go by when you cannot be in Key West.

Earlier in the week, the Masquerade March walks through Old Town with anyone in costume, no float required. Once the parade has passed and the corner empties, the rest of our live webcams from around the world are still running in other time zones.