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Jimmy Buffett’s Favorite Dive Bar Secrets Revealed

A boatload of Key West tourists in search of a cold drink on a balmy day make a beeline to Sloppy Joe’s, an oft-crowded saloon that trades in Hemingway lore, as it was a favorite watering hole of the literary luminary. Those who’ve done a little more homework might head to Captain Tony’ Saloon, a cave-like bar that was formerly the first location of Sloppy Joe’s and also a Hemingway haunt. And if you’ve really dug deep into the Conch Republic’s repositories of revelry, you navigate your way to Chart Room for the dive bar’s relaxed vibe, to mix and mingle with locals, and for tales that sound tall but are mostly true.

The tiny, dimly lit bar is housed in Pier House Resort, a luxurious yet laidback property hemmed by Key West’s bustling Duval Street on one side and the ocean on the other, that first welcomed guests in 1967. The bar was not part of the resort’s original plan, but within weeks of opening, when someone asked where the bar was, the plan changed. A hotel room was hastily cleared out and turned into Chart Room, and little has changed in the almost 60 years since. These inauspicious beginnings belie the history the bar holds. Its walls and ceiling, covered in pinned-up faded dollar bills and amber-with-age photos and maps, have seen a lot. Read more…

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