The massive crowd of bikers in front of Sloppy Joe’s on the closed down Duval Street in Key West. They all came for the annual Florida Keys Poker Run. Photo by Bill Andrews/Miami Herald Staff
Miami Herald File
Key West is a city of change.
Shipwreck capital. Cigar-making center. Navy headquarters. LGBTQ village. Tourist town.
Duval Street, the Southernmost City’s commercial and entertainment heart, also has seen change. The hardware and five-and-dime stores of an old downtown are long gone. Shorty’s Diner, Harry Truman’s favorite spot for grits and grunts, closed in 1989. The Kress store became Fast Buck Freddie’s, then became a CVS.
The city and its main street have survived storms and business upheavals.
Over the past two decades, stores and restaurants have come and gone. Floodwaters have risen and receded. Buildings have been renovated and abandoned and renovated again.
But one thing has stayed the same: Key West’s Duval Street is an attraction.
Let’s look back to the 1990s and early 2000s.
Flooding and storms
Bill Tsagnis, manager of The Quay Restaurant on Duval Street, sweeps water on a street empty of tourists in October 1998. J. Albert Diaz Miami Herald File
Hurricane Georges prep in Key West, Florida — Eli Aroch boards up the Key West Gift Shop on Duval Street in preparation of Hurricane Georges in September 1998.. Charles Trainer Jr. Miami Herald File
A man crosses eastern Duval Street in Key West past the southernmost house in surge floods caused by Hurricane Wilma in October 2005. Tim Chapman Miami Herald File
.Bob Graham, a local business owner, photographs Sloppy Joes Bar on Duval street in Key West flooded by the surge of hurricane Wilma on Oct. 24, 2005. Tim Chapman Miami Herald File
Jeff Naset hauls a load of plywood along Duval Street on Sept. 10, 2004, as he helps his family board up the Birkenstock of Old Town Footwear store in Key West, in anticipation of the arrival of Hurricane Ivan. WILFREDO LEE AP
A Key West man and his puppy walk past the boarded-up Yo Sake Japanese Restaurant and Sushi Bar on Duval Street. It was one of the few businesses to board up for Hurricane Lili in October 1996. Miami Herald File
Raymond Captain is prepared to rescue people as he stands on Duval Street in Key West on Sept. 9, 2017. Hurricane Irma is approaching the Florida Keys and some residents refused to be evacuated. CHARLES TRAINOR JR Miami Herald File
Stores, restaurants and landmarks
Call of the Wild decorations spring up all over Key West, including a pair of tiger claws and the cobwebby hangings at Fast Buck Freddie’s on Duval Street. Nancy Klingener Miami Herald File
Jim Heidenreich put the finishing touches on a giant Conch Shell on the second story of Fast Back Freddie’s on Duval Street. Susana Bellido Miami Herald File
Tourists clog Duval Street in 2004. Tim Chapman Miamiu Herald File
Banners on Duval Street and Truman Avenue encourage Key Westers to share the road. Susana Bellido Miami Herald File
Amy Ervin of Key West takes time out to surf the web at the Internet Isle Cafe on Duval Street. Miami Herald File
Buddy “BO” Owens gets things going at the deep fryer at his popular BO’s Fish Wagon at the corner of William and Caroline streets. Owen was a standout athlete for Key West High School. He previously operated BO’s on Duval Street. Herald Staff
The San Carlos Institute on Duval Street has hosted cultural events since its renovation. Susana Bellido Miami Herald File
The arch marking the entrance to Bahama Village, at Petronia Street just off Duval Street, returned after more than a year. The arch was refurbished and the pillars holding it re-done. Nancy Klingener Miami Herald File
Tattoo Artist J.D. Hoadley applies his trade at Southermost Tattoo parlor on Duval Street in Key West. PATRICK FARRELL Miami Herald File
Tourists gaze at the sign taped to the door at Rumrunner’s on Duval Street. It read: “In mourning. Closed today due to death in family.” General manager Mark Sumner was shot and killed. A former bouncer is charged with the crime. Nancy Klingener
The massive crowd of bikers in front of Sloppy Joe’s on the closed down Duval Street in Key West. They all came for the annual Florida Keys Poker Run. Photo by Bill Andrews/Miami Herald Staff Bill Andrews Miami Herald File
In this picture, released by the Florida Keys News Bureau, former President Bill Clinton prepares to enter singer Jimmy Buffett’s restaurant “Margaritaville” on Duval Street in Key West, Fla., Saturday, Jan. 22, 2005. Clinton was in Key West with wife, Sen. Hillary Rodham Clinton D-N.Y., for two weekend political fund-raisers on the subtropical island. (AP Photo/Florida Keys News Bureau, Rob O’Neal) AP File
Actor Jim Belushi arrives at the grand opening of Planet Hollywood in Key West. Belushi was greeted by fans who waited for hours on Duval Street to catch a glimpse of the celebrities attending the party. Hector Gabino Miami Herald File
Tony Pro, a University of Central Florida student on spring break, walks Pancho the iguana on a leash. Susana Bellido Miami Herald File
Deputies from the Monroe County Sheriff’s Office watch over the crowd at Fantasy Fest on Duval Street. Miami Herald File
Tourist Janet Sternberg of McMinnville, Tenn., has her picture taken with Captain Booty, retired teacher Bob Kelley, in front of Sloppy Joe’s on Duval Street during her cruise ship stop in Key West. Cammy Clark Miami Herald File
Margo, the oldest drag queen at 801 Bourbon Bar, located on Duval Street, gets into her tights in 2001. Richard Patterson Miami Herald File
A group of roaming Elvis impersonators pose for pictures for Fantasy Fest partygoers on Duval Street. Miami Herald File
Sushi beckons tourists to come in and see the show performed at the 801 Bar on Duval Street in Key West in 2002. Tim Chapman Miami Herald File
This story was originally published
June 22, 2022 11:19 AM.
Day Editor Jeff Kleinman, born and raised in South Florida, oversees breaking, public service and trending news coverage.
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