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Recently, there has been talk about re-opening mail routes to Cuba, which is only 90 miles from the most southern point in the United States, Key West, Florida. The first contract airmail route to Cuba was awarded to Pan American Airways. Foreign Air Mail Route 4 from Key West to Havana had 7 weekly round-trip flights, starting on May 29, 1928. John T. McCoy Pan American World Airways, Fokker F-7 (F.VII) 1968 SFO Museum Collection Gift of the Pan Am Historical Foundation 2003.058.001 This image was posted on January 12, 2016.