Cy Caldwell sitting on his plane in Key West Harbor.

TODAY in KEY WEST HISTORY / October 19, 19271927 To fulfill its contract with the U.S. Post Office, Pan American Airlines hired pilot Cy Caldwell to fly a singled-engine seaplane from Key West to Havana. He left Key West at 8:04 a.m. carrying seven sacks of mail, containing about thirty thousand letters. He landed in Havana sixty-two minutes later and saved the airline which could not begin regular service with its own planes until October 28.

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