c. 3500 B.C.E.	The first humans reach Cuba from South America's Orinoco basin. The Gauanajatabeys settle in present-day Pinar del Río as hunter-gatherers, followed by the Ciboneys who settle along the south coast as farmers and fishermen.
c. 1250 C.E.	The Carib tribe chases the Taíno tribe from Hispaniola to Cuba. Upon their arrival, the Taínos displace many of the indigenous Gauanajatabeys and Ciboneys.
1492	Columbus voyages along Cuba's north coast. He believes Cuba is part of the coast of Asia. Columbus describes the native Taínos as "the best people in the world, without knowledge of what is evil; nor do they murder or stealÉAll the people show the most singular and loving behaviorÉand are gentle and always laughing."
1508	Sebastián de Ocampo circumnavigates Cuba, proving that it is an island.
1510s	The encomienda system takes root in Cuba; each Spanish landowner is allotted between 40 and 200 indentured Indian servants, who are to be freed when they convert to Christianity. Many are worked to death.
1512	Diego Velázquez lands at Baracoa, founding the first Spanish town. Hatuey, an Indian chief who fought the Spanish, is captured and burned at the stake. A Franciscan monk tries to baptize him, but Hatuey objects, declaring that he never wants to see another Spaniard, not even in heaven.
1514	The first seven Spanish settlements are established: Bayamo, Puerto Principe (today's Camagüey), San Cristóbal de la Habana, Sancti Spíritus, Santiago de Cuba, and Trinidad.
1515	Santiago de Cuba becomes Cuba's capital.
1518	Velázquez, not satisfied with the amount of gold unearthed in Cuba, sponsors the brutal conquest of Hernán Cortés. Cortés sails from Cuba to subdue the Aztec empire.
1519	Havana is established on its present site.
1522	The first African slaves are brought to Cuba. Unlike the British, the Spanish keep the slaves together in tribal groups, allowing for greater preservation of tribal traditions.
1542	The encomienda system, first established in the 1510s to provide Indian labor for colonist plantations, is abolished. Plantations rely more and more on slave labor.
1550	As a result of smallpox and other infectious diseases brought by the Spanish, fewer than 5,000 indigenous Cubans remain.
1555	French pirate Jacques de Sores sacks Havana.
1564	Spanish fleets laden with New World riches first assemble in Havana harbor for an annual voyage to Spain as a flota (fleet).
1589	Havana and Santiago de Cuba are fortified against pirates.
1607	Havana replaces Santiago de Cuba as capital of Cuba.
1628	Dutch pirate Piet Heyn captures the flota.
1674	The construction of city walls around Havana begins.
1700	Tobacco farming has replaced cattle ranching as Cuba's most important industry.
1717	The Spanish crown grants itself a monopoly to buy and sell tobacco.
1728	The University of Havana is founded.
1762	The British capture Havana. During their eleven-month occupation, they bring 4,000 slaves from Africa to Cuba and throw open trade to British colonies in North America.
1763	The British trade Cuba back to Spain in exchange for Florida.
1765	Spain allows Cuba to trade directly with seven Spanish ports. This comes as a legacy of the freer trade allowed during the British occupation.
1790	Tens of thousands of African slaves are captured, brought to Cuba, and forced to work on sugar plantations.
1800	By this time, sugar has replaced tobacco as Cuba's main export.
1809	Former U.S. President Thomas Jefferson writes to his successor, James Madison, that Cuba would be "the most interesting addition" to the United States.
1810	Madison decides to leave Cuba under the domination of Spain, a relatively weak country. Madison makes it clear, however, that the United States would not look kindly upon attempts by any other country -- especially Great Britain -- to acquire Cuba and her resources.
1818	Spain allows Cuba to trade directly with all other countries.
1820	Diplomatic pressure from Britain forces Spain to say it will halt the slave trade. In reality, slavery continues.
1823	U.S. Secretary of State John Quincy Adams predicts that the United States will annex Cuba within 50 years.
1825	Most of Spain's former Latin American colonies have gained independence.
1830s -- 1870s	Cuba's sugar industry becomes the most mechanized in the world. By 1850, sugar makes up 83% of Cuba's exports, of which 40% goes directly to the United States. Sugar is one element of a triangular trading system in which sugar goes to the United States, rum goes to Africa, and slaves go to Cuba.
1837	Sugar planters build the first railway to bring raw sugarcane to the mills.
1848	The United States finally acts on its long-held desire to acquire Cuba. The U.S. government offers to buy Cuba from Spain for $100 million. Spain refuses.
1850	Narciso López raises the Cuban flag for the first time as part of a botched attempt to annex Cuba to the United States.
1853	José Martí, Cuba's national hero, is born in Havana.
1854	The United States offers Spain $130 million for Cuba; Spain again declines to sell the island.
1865	No more African slaves are imported to Cuba. Instead, indentured Chinese laborers and Mexican Indians cut sugarcane.
1868 -- 1878	First War of Independence The rebels lose. Cuba remains a Spanish colony.
1879	Spain abolishes slavery, decreeing that slaves must continue working for their masters as "apprentices" for in return for year-round room and board.
1886	The "apprenticeship" system ends. Plantation owners pay former slaves to cut cane from January to July and have no responsibility to feed or house them.
1895 to 1898	Second War of Independence
1895	José Martí is killed in a skirmish at Dos Rios in eastern Cuba.
1898	January -- The United States dispatches the U.S.S. Maine to Havana under the pretext of protecting American citizens in Cuba. February -- The Maine explodes in Havana harbor, killing 260 officers and crew. The United States blames Spain, although today no one is sure exactly who blew up the ship. April -- The U.S. Congress declares that Cuba has the right to independence and declares war on Spain. August -- Spain and the United States sign a bilateral armistice. Cuba is not represented at the negotiations. December -- Spain and the United States sign the Treaty of Paris. The United States gains control over four new territories: Cuba, Puerto Rico, the Philippines and Guam. Although Cuba is granted independence, the United States installs a military government in Havana to "pacify" Cuba.
1901	The Platt Amendment passes in Congress. This amendment gives the United States the right to intervene militarily in Cuba whenever the U.S. government decides such intervention is warranted.
1902	Tomas Estrada Palma is elected president of Cuba. U.S. military occupation formally ends.
1903	The United States founds a naval base at the mouth of Guantánamo bay.
1906	The United States intervenes when Cuba's second election is marred by accusations of fraud. The United States holds power through January 1909.
1917	Former slaves in Pinar del Río revolt against racial discrimination. The United States sends soldiers in ostensibly to stop the revolt but also to ensure a steady supply of sugar to the United States during World War I.
1925	The first Communist Party is founded.
1933	President Gerardo Machado y Morales is toppled by a general strike. Army sergeant Fulgencio Batista takes command as army chief of staff.
1934	Franklin Roosevelt implements a "good neighbor" policy towards Latin America. Essentially, this policy means that the United States agrees not to intervene in Latin American countries' internal affairs. This policy leads to the Platt Amendment's abrogation.
1940	Batista drafts a democratic constitution guaranteeing many rights and is elected president. Batista gains U.S. support for his endorsement of the Allied war effort.
1944	Batista allows free elections, but his preferred candidate loses to Ramon Grau San Martin. After the inauguration, Batista goes into self-imposed exile in Florida.
1952	After eight years out of power, Batista stages a coup. Batista suspends the Constitution and cancels elections, preventing a young Fidel Castro's almost certain election to the House of Representatives. U.S. President Harry Truman quickly recognizes Batista's dictatorship.
1953	Rebel leader Fidel Castro leads a failed attack on the Moncada barracks, is captured, and sentenced to 15 years in prison.
1955	February -- Batista wins the election by rigging it in his favor; to celebrate, he frees all political prisoners, including Castro. Castro flees to Mexico. December -- Students at Havana University form the Directorio Revolucionario.
1956	Castro's band of rebels, trained in Mexico, land in Oriente province. They are defeated, but Castro and an Argentine doctor named Ernesto "Che" Guevara escape into the mountains.
1957	February -- A New York Times reporter interviews Castro and his group, portraying them as romantic, revolutionary heroes. American public support limits the amount of overt military support U.S. officials can provide to Batista. March -- Havana University student members of the Directorio Revolucionario attempt to assassinate Batista. Most are killed.
1958	May -- Batista sends an army into the Sierra Maestra mountains to take out Castro's guerrillas. The rebels defeat the army and capture their guns. December -- Che Guevara captures Santa Clara.
1959	January -- Batista flees to the Dominican Republic. Guevara enters Havana. Manuel Urrutia assumes the presidency. February -- Castro is named prime minister. The revolutionary government moves to cut rent and electricity rates and abolishes racial discrimination. April -- Vice President Richard Nixon receives Castro at the White House, accusing Castro of being a Communist. After the meeting, Nixon sets in motion the chain of events that would lead to the Bay of Pigs invasion. May -- All Cuban estates larger than 400 hectares are nationalized during the First Agrarian Reform. Prior to the reform, five U.S. sugar companies owned or controlled more than two million acres. The United States protests, saying compensation is too low. July -- President Urrutia resigns after criticizing the land reforms. Osvaldo Dorticós replaces him. October -- Huber Matos attempts a counterrevolutionary coup. Cuban émigrés from Miami fly a B-25 bomber over Havana. Castro purges the judicial system in response.
1960	February -- Soviet Vice Premier Anastas Mikoyan visits Cuba. Trade documents are signed in which the USSR agrees to replace many technicians and professionals who left in the wake of the revolution. March -- a French ship explodes mysteriously in Havana harbor. Cuba accuses the CIA, and relations with the United States deteriorate further. May -- Cuba resumes diplomatic relations with the Soviet Union. Also, Cuba requires foreign-owned oil refineries to process crude oil arriving from the Soviet Union at favorable rates. June -- The oil refineries refuse to process Soviet crude oil. In response, Cuba nationalizes these foreign refineries. July -- Cuba nationalizes the United Fruit Company's holdings in Cuba, which total some 270,000 acres. August -- The Cuban government nationalizes the American-owned telephone and electricity companies, along with 36 sugar mills, totaling $800 million in U.S. assets. In response, the U.S. pushes through a resolution by the Organization of American States condemning "extra-continental" (Soviet) intervention in the Western hemisphere. September -- Cuba establishes diplomatic relations with communist China. October -- Most Cuban banks are nationalized. Washington imposes a partial trade embargo. As a result, Cuba nationalizes all remaining U.S. businesses in the country.
1961	April 15, 1961 -- Some 1,400 Cuban émigrés trained by the CIA land at the Bay of Pigs. Cuban planes attack their supply ships, leaving the troops stranded on the beaches without most of their equipment. After about 200 were killed, they surrendered. Eventually, 1,197 of the men were "ransomed" by the United States for $53 million in food and medicine. During an April 16 speech honoring Cuban airmen killed in the raids, Castro proclaims the socialist nature of the Cuban revolution for the first time. June -- Americans declare a full trade embargo.
1962	April -- Soviet premier Nikita Khruschev installs medium-range missiles in Cuba that are capable of hitting any target in the United States. October 22 -- President Kennedy orders the U.S. Navy to stop Cuba-bound Soviet ships in international waters to carry out searches for missiles. October 28 -- Khruschev orders the missiles dismantled.
1963	Second agrarian reform fixes maximum private holdings at 65 hectares.
1967	Che Guevara, who was in Bolivia trying to foment revolution, is captured and shot in the presence of U.S. advisors.
1972	Cuba joins Soviet-led Comecon trading block, resulting in greater economic dependency on the Soviet Union.
1975	March -- Cuba's Family Code, a law intended to promote equality between men and women in all aspects of Cuban life, goes into effect. October -- Cuba provides military aid to Angola in asserting its independence from Portugal.
1976	The third constitution replaces the Ley Fundamental (Fundamental Law) enacted in 1959. Fidel Castro replaces Osvaldo Dorticós as president.
1979	The Non-Aligned Movement holds its summit in Havana, gaining Castro credibility.
1980	Twelve Cubans demand asylum at the Peruvian embassy in Havana. The embassy refuses to turn them over to Castro. Within 72 hours, 11,000 Cubans huddled in the embassy, demanding asylum. The international media picked up the story, and Castro decided to allow them to leave. He took this opportunity to empty the prisons of dissidents and handily disposed of 120,000 critics of his regime. These critics were airlifted to America in what came to be called the "Mariel boatlift."
1990	With supplies from the former Soviet Union dwindling, Castro declares a five-year austerity program called the "special period" -- essentially ensuring wartime rationing during a time of peace. With the dissolution of the Soviet Union, Cuba experiences an 85% drop in imports, and a 70% drop in purchasing power.
1991	Boris Yeltsin takes power as the Soviet Union collapses. All subsidies and supplies to Cuba come to a grinding halt.
1993	Market reformers are appointed to positions of power. Tourism begins to surpass sugar production as Cuba's main industry. Cuban citizens are allowed to possess U.S. dollars.
1994	More than 20,000 Cubans try to emigrate on rafts to the United States. Most are picked up at sea and shipped to Guantánamo naval base.
1996	The United States tightens the blockade of Cuba through the Helms-Burton Act. This act, pushed through during the presidential campaign, provides that any future president wishing to modify or rescind the embargo must seek congressional approval.
1998	Pope John Paul II visits Cuba, denouncing the U.S. embargo as immoral but pressing for greater political and economic liberty in Cuba.
1999	The Elián González dispute prompts public discussion of U.S.-Cuba relations.