Key West is much closer to Havana than it is to Miami. In 1890, Key West had a population of nearly 18,800 and was the biggest and richest city in Florida. Half the residents were said to be of Cuban origin, and Key West regularly had Cuban mayors, including the son of Carlos Manuel de Céspedes, father of the Cuban Republic, who was elected mayor in 1876. Cubans were actively involved in reportedly 200 factories in town, producing 100 million cigars annually. José Martí made several visits to seek recruits for Cuban independence starting in 1891 and founded the Cuban Revolutionary Party during his visits to Key West.
The Battleship USS Maine sailed from Key West on its fateful visit to Havana, where it blew up, igniting the Spanish-American War. Crewmen from the ship are buried in Key West, and the Navy investigation into the blast occurred at the Key West Customs House.
Pan American Airlines was founded in Key West, originally to fly visitors to Havana, in 1926. The airline contracted with the United States Postal Service in 1927 to deliver mail to and from Cuba and the United States. The mail route was known as the "Key West, Florida Havana Mail Route".
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