Southernmost point in the continental US. President Harry Truman's Little White House. PanAm Airlines. Located almost at the end of Florida. You can't drive any further than this but Dry Tortugas National Park is part of Florida (you have to take a 2.5 hour boat ride to the site). I missed the turn for the southernmost point buoy and only spend a day on Key West (expensive) so I'll have to update this later when I can spend more time in the off-season.

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First Flight Island Restaurant & Brewery: PanAm World Airways ticket office was originally located on this site in 1927. Have a drink in the Crash Bar...where Sikorsky sea plane crashed through the ceiling!