Captain Tony’s Saloon

Captain Tony's Saloon The oldest bar in town is Captain Tony’s Saloon, which also happens to be a very popular tourist spot, even if you don’t have a drink. It is one of the must-sees of Old Town, if you are interested in crossing things off your list. It’s on Greene Street, just a few doors in from Duval so you can’t miss it if you’re walking up or down Duval. Captain Tony’s Saloon full of Key West lore. For example, Hemingway met his third wife, Martha Gellhorn, here. Captain Tony himself is a local fixture. He doesn’t own the bar anymore, but he was made honorary Mayor of Key West (he was actually elected once). Look for posters with his face on them, with his original words: All you need in life is a tremendous sex drive and a great ego–brains don’t mean a sh**t. That’s one great souvenir.

Actually, if you really like Captain Tony’s take on life, you can buy almost anything with his face and words of wisdom on them. Mugs, t-shirts, panties, beach towels, and magnets. He’s a local hero, and now he tours the country talking about his life. You can contract him to speak at your next event if you so desire.

The bar itself has had a very eventful life as well, just like Captain Tony. It’s gone through so many transformations and some confusion exists amongst visitors who want to visit the bar Hemingway made famous. Is it Captain Tony’s Saloon or Sloppy Joes, now on Duval? Good question. It depends on how you look at it. In the years between 1933 and 1937, this bar on Greene Street was called Sloppy Joe’s. These are the years Hemingway frequented the bar.  You can’t miss either bar, on end of Duval Street nearest Mallory Square.