Havana was founded in the sixteenth century displacing Santiago de Cuba as the island's most important city when it became a major port for Atlantic shipping, particularly the Spanish treasure fleet.

This bay is very good and can host many ships, which I visited few years after the Discovery... few are in Spain, or elsewhere in the world, that are their equal...[2] This superb harbor at the entrance to the Gulf of Mexico with easy access to the Gulf Stream, the main ocean current that navigators followed when traveling from the Americas to Europe, led to Havana's early development as the principal port of Spain's New World colonies.

Havana was the sixth town founded by the Spanish on the island, called San Cristóbal de la Habana by Pánfilo de Narváez: the name combines San Cristóbal, patron saint of Havana, and Habana, of obscure origin, possibly derived from Habaguanex, a Native American chief who controlled that area, as mentioned by Diego Velasquez in his report to the king of Spain.

Cuba, during the first years of the Discovery, provided no immediate wealth to the conquistadores, as it was poor in gold, silver and precious stones, and many of its settlers moved to the more promising lands of Mexico and South America that were being discovered and colonized at the time.

The legends of Eldorado and the Seven Cities of Gold attracted many adventurers from Spain, and also from the adjacent colonies, leaving Havana and the rest of Cuba largely unpopulated.

Goods traded in Havana included gold, silver, alpaca wool from the Andes, emeralds from Colombia, mahoganies from Cuba and Guatemala, leather from the Guajira, spices, sticks of dye from Campeche, corn, manioc, and cocoa.

The thousands of ships gathered in the city's bay also fueled Havana's agriculture and manufacture, since they had to be supplied with food, water, and other products needed to traverse the ocean.

The Castillo de la Real Fuerza defended the city's center, and doubled as the Governor's residence until a more comfortable palace was built.

New buildings were constructed from the most abundant materials of the island, mainly wood, combining various Iberian architectural styles, as well as borrowing profusely from Canarian characteristics.

On November 30, 1665, Queen Mariana of Austria, widow of King Philip IV of Spain, ratified the heraldic shield of Cuba, which took as its symbolic motifs the first three castles of Havana: the Real Fuerza, the Tres Santos Reyes Magos del Morro and San Salvador de la Punta.

The episode began on June 6, 1762, when at dawn, a British fleet, comprising more than 50 ships and a combined force of over 11,000 men of the Royal Navy and Army, sailed into Cuban waters and made an amphibious landing east of Havana.

[6] The British seized the heights known as La Punta on the east side of the harbor and commenced a bombardment of nearby El Morro Castle, as well as the city itself.

After a two-month siege,[7] El Morro was attacked and taken, only after the death of the brave defender Luis Vicente de Velasco e Isla, on 30 July 1762.

[7][8] Though Havana, which had become the third largest city in the new world, was to enter an era of sustained development and strengthening ties with North America, the British occupation was not to last.

The treaty gave Britain Florida in exchange for the city of Havana on the recommendation of the French, who advised that declining the offer could result in Spain losing Mexico and much of the South American mainland to the British.

Havana's theaters featured the most distinguished actors of the age, and prosperity amongst the burgeoning middle-class led to expensive new classical mansions being erected.

Throughout the century, Havana was enriched by the construction of additional cultural facilities, such as the Tacon Teatre, one of the most luxurious in the world, the Artistic and Literary Liceo (Lyceum) and the theater Coliseo (Colosseum).

Numerous luxury hotels, casinos and nightclubs were constructed during the 1930s to serve Havana's burgeoning tourist industry, strongly rivaling Miami.

At the time, Havana became an exotic capital of appeal and numerous activities ranging from marinas, grand prix car racing, musical shows and parks.

Havana achieved the title of being the Latin American city with the biggest middle class population per-capita, simultaneously accompanied by gambling and corruption where gangsters and stars were known to mix socially.

A gallery of black and white portraits from the era still adorn the walls of the bar at the Hotel National, including pictures of Frank Sinatra with Ava Gardner, Marlene Dietrich and Gary Cooper.

One of the most well-known visitors and resident to the area was the American author Ernest Hemingway (1899–1961), who quoted, "In terms of beauty, only Venice and Paris surpassed Havana".

[11] After the revolution of 1959, the new government promised to improve social services, public housing, and official buildings; nevertheless, shortages that affected Cuba after Castro's abrupt expropriation of all private property and industry under a strong communist model backed by the Soviet Union followed by the U.S. embargo, hit Havana especially hard.

After the Soviet Union collapsed in 1991, its subsidies to Cuba ended, costing the Cuban government billions of dollars, and causing a severe economic downturn.

[14] After 50 years of prohibition, the communist government increasingly turned to tourism for new financial revenue, and has allowed foreign investors to build new hotels and develop hospitality industry.