Plano borrador de las posesiones los Señores Forbes y Compañia entre los Rios Apalachicola y San Marcos en la Florida Occidental.

Founded by the Spanish, San Cristóbal de la Habana by Pánfilo de Narváez, was a small trading port and suffered regular attacks by buccaneers, pirates, and French corsairs. Pirate attacks convinced the Spanish Crown to protect its ships heading to Spain by assembling them in one large fleet, which would traverse the Atlantic Ocean protected by the Spanish Armada (Spanish Navy). After 1561, all ships headed for Spain were required to assemble in the Havana Bay waiting for the best weather, and together, departing for Spain by September. This boosted commerce and development of the adjacent city of Havana. Ships from all over the New World carried products first to Havana, in order to be taken by the fleet to Spain. Ships also had to be supplied with food, water, and other products. In 1563, the Spanish Governor of the island moved his residence from Santiago de Cuba to Havana, the de-facto capital of the island. By the middle of the 18th century, Havana had more than 70,000 people, and was the third-largest city in the Americas, ahead of Boston and New York. The city was captured by the British in 1762 but returned it to Spain in exchange for Florida. Slavery was legal in Cuba until 1886 and after the Confederate States of America were defeated in the American Civil War in 1865, many former slaveholders continued to run plantations by moving to Havana. As trade between the Caribbean and North American states increased, Havana became a flourishing and fashionable city. During this period Havana became known as the Paris of the Antilles. At the beginning of the 20th century, Cuba was occupied by the United States. The US occupation ended in1902 and Cuba became a republic. U.S. prohibition on alcohol from 1920 to 1933 helped Havana to become a destination for sailing, car racing, musical shows, organized crime, and sex tourism. Luxury hotels, casinos, nightclubs were producing more revenue than Las Vegas. In 1958, about 300,000 American tourists visited the city. After the revolution of 1959, Fidel Castro promised to improve social services, public housing, and official buildings. Communism model, expropriation of all private property was followed by the U.S. embargo, which hit Havana especially hard. In 1991 Soviet subsidies ended, and a severe economic downturn made many to believe that communism soon collapse, however, contrary to events in Europe, Cuba's communist government persists to this day.

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