Relive the Wild Nights of Key West at the Legendary Old Anchor Inn!
Nicknamed “The Snake Pit”, the Old Anchor Inn was a wild bar back in the day.
Three shots of tequila for a buck!!!
The picket fence lining the sidewalk was erected to appease the city because they had too many complaints of patrons falling out the front door. It even had a balcony once, but people kept falling over.
When Jimmy Buffett came to Key West in 1971, folks slept in their cars behind the bar and the restroom floors were often flooded where you had to walk on bricks to keep your shoes dry.
A line scribbled on the bathroom wall was used by Jimmy in his 1981 song “If I could just to get it on paper”, the scrawled message said “Life and Ink run out at the same time”-Squid.
Bud and Dorothy Mac Arthur’s place was always crowded, but more at three in the morning than at three in the afternoon.
During the wee hour dance marathons Joe Cocker singing “She came in through the bathroom window” played 20-30 times a night.
Men in clothes swiped from local clothes lines gambled tens and twenties at the pool table.
Murals on the inside of the window shutters were painted by “Monkey Tom” swapped for a “bottomless” bar tab.
For a young Jimmy this seedy establishment provided a source of inspiration for more than a few stories. One story is that he escaped through the bar’s upstairs apartment after a woman had gone crazy on lower Duval through assorted curse words and a broken beer bottle.
Today the building is the Red Garter Saloon, which provides adult entertainment that offers a lively atmosphere with a stage performance and a bar.
David Garland Mar 24, 2026 Key West FL Back in Time Bars Things To Remember
Mar 24, 2026
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