Captain Tony's Saloon, famous in its own right, is on the site of the original Sloppy Joe's, the one where Hemingway hung out. Other celebrities like Tennessee Williams, Truman Capote, Shel Silverstein dropped by here, too. The bar names a bar stool after every celebrity who visits. Jimmy Buffet got his start at Tony's, being paid in tequila. Capt. Tony died at age 92 in 2008, but his spirit lives on in what is said to be Key West's oldest bar - along with other spirits. Check it out during the Fantasy Fest around Halloween.

capttonyssaloon.com