Just around the corner from Duval’s beaten path, this smoky old bar is about as authentic as you’ll find. It comes complete with old-time regulars who remember the island before cruise ships; they say Hemingway drank, caroused, and even wrote here. The late owner, Capt. Tony Tarracino, was a former controversial Key West mayor—immortalized in Jimmy Buffett’s “Last Mango in Paris.”