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1775–83: The thirteen North American colonies rebel against Great Britain and establish the United States, thereby encouraging commerce between the newly independent nation and Cuba.
1818: Spain opens Cuban ports for international trade, especially with the United States. U.S.-Cuba trade increasingly replaces Spanish commercial relations with the island.
1819: The United States acquires Florida, which had been governed by Spain as part of the Captaincy General of Cuba.
1823: In April, Secretary of State John Quincy Adams writes a letter to U.S. Minister to Spain Hugh Nelson, anticipating the likelihood of U.S. annexation of Cuba within half a century. In December, Father Félix Varela arrives in New York City after fleeing Spain because of his pro-independence ideals, and becomes the first Spanish-speaking Catholic priest in the Diocese of New York. The exiled Cuban poet José María Heredia also arrives in Boston in December, and later moves to New York City, where he writes his famous Romantic ode, "Niagara" (1825).
1848: President James Polk offers $100 million to purchase Cuba from Spain, which declines the offer.
1848–51: The Venezuelan-born General Narciso López, exiled in the United States, organizes three abortive filibustering expeditions to liberate Cuba from Spain. The Spanish government executes López and fifty-one members of his last expedition in August 1851.
1850: The first Cuban flag, designed by Narciso López, is hoisted in New York City.
1851: The Spanish government executes Joaquín de Agüero, the leader of an annexationist uprising in Puerto Príncipe (present-day Camagüey), in May. Isidoro Armenteros, the leader of another rebellion in Trinidad, is put to death in August.
1853: In March, William Rufus DeVane King takes his oath of office as vice president of the United States near Matanzas, Cuba. He dies of tuberculosis the next month in his home in Alabama.
1854: During the administration of President Franklin Pierce, U.S. diplomats propose to purchase Cuba from Spain for up to $120 million in a secret document known as the Ostend Manifesto. The plan fails when President Pierce rejects it as politically unacceptable.
1865: Cuba exports 65 percent of its sugar to the United States and only 3 percent to Spain.
1868: The first Cuban war of independence from Spain, known as the Ten Years' War, begins. The United States admits 10,061 immigrants from Cuba between 1868 and 1878.
1869: The Spanish-born entrepreneur Vicente Martínez Ybor, a sympathizer of Cuban independence, flees the island and establishes a cigar factory in Key West, Florida.
1870: The U.S. census enumerates 1,565 persons born in Cuba and residing in New York City (including Brooklyn).
1875: Carlos Manuel de Céspedes y Céspedes, son of one of the leaders of the Ten Year's War, is elected the first Cuban-born mayor of Key West.
1878: The Pact of Zanjón ends the Ten Years' War in February. Toward the end of the year, the first Cuban professional baseball league is founded.
1879–80: A second war of independence begins, known as "The Little War," but is crushed by Spain after nine months.
1880: The census enumerates 2,388 Cuban residents of Key West, about one-fourth of the city's population.
1881: The Cuban journalist, poet, and politician José Martí settles in New York City, where he writes in both Spanish and English for several Latin American and U.S. newspapers.
1885: Martínez Ybor and his associates found Ybor City near Tampa, Florida, attracting many Cuban cigar workers.
1886: Spain abolishes slavery in Cuba.
1890: Tampa (which then includes Ybor City) has 2,424 Cuban residents, 44 percent of the city's inhabitants.
1892: Martí founds the pro-independence newspaper Patria in New York City in March and the Cuban Revolutionary Party in April.
1895: The third and final Cuban war of independence from Spain begins in February. Martí dies in battle against the Spanish in Cuba in May.
1898: The USS Maine explodes in Havana Harbor in February. The United States declares war against Spain in April. The Spanish-American War ends in August. Spain relinquishes control of Cuba (as well as Puerto Rico, the Philippines, and Guam) through the Treaty of Paris signed in December.
1899: The United States commences the formal military occupation of Cuba on January 1st.
1900: A constituent assembly convenes to prepare a new constitution in Cuba.
1901: In March, the U.S. Congress approves the Platt Amendment, stating that it may intervene militarily in Cuba to defend U.S. interests, and requires the Cuban constituent assembly to incorporate the statute into the new constitution. In June, the constituent assembly adopts the Platt Amendment by a vote of sixteen to eleven, with four abstentions.
1902: On May 20, the United States ends the military occupation of Cuba, formally inaugurating the Cuban republic. Tomás Estrada Palma, a naturalized U.S. citizen, is elected first president of Cuba.
1902–1911: U.S. citizens are the second largest group of foreign immigrants (after Spaniards) in Cuba, with 16,150 persons. Many are managers, technicians, and employees in U.S. sugar companies and in public services, as well as business owners.
1903: The United States and Cuba sign a treaty incorporating the Platt Amendment in May. In July, Cuba leases the sites of Bahía Honda and Guantánamo to the United States as coaling and naval stations. The U.S.-Cuba Reciprocal Commercial Convention, signed in December, concedes a 20 percent reduction to Cuban agricultural products entering the U.S. market in exchange for reductions between 20 and 40 percent on U.S. imports to Cuba.
1904: Cuba and the United States sign the Hay-Quesada Treaty, which recognizes Cuba's ownership of the Isle of Pines but is not ratified by the U.S. Senate until 1925.
1906–9: The U.S. military occupies Cuba to put down an insurrection after the resignation of President Estrada Palma and governs the island through a provisional government led by Charles Edward Magoon.
1912: In May, the U.S. government sends Marines to Cuba to protect U.S. property, in response to an armed rebellion (known as the "race war") by Afro-Cubans in Oriente Province. In December, the United States cedes its rights over Bahía Honda in exchange for larger facilities in Guantánamo Bay.
1916: U.S. chocolate manufacturer Milton Hershey begins to acquire land in Cuba. In 1918, he builds Central Hershey, a large sugar mill and surrounding town, about thirty-five miles east of Havana. Hershey's Cuban holdings are sold in 1946 to the Cuban Atlantic Sugar Company.
1917–22: The United States once again leads a military intervention in Cuba after a disputed presidential election (following the reelection of Mario García Menocal) and armed rebellion led by former President José Miguel Gómez.
1923: The U.S. Legation in Havana is raised to Embassy status.
1925: The U.S. Senate ratifies the Hay-Quesada Treaty.
1927: Pan American Airways inaugurates its first international flight between Key West and Havana.
1928: President Gerardo Machado unconstitutionally extends his reelection term to six years, provoking armed insurrections.
1930: The U.S. Hawley-Smoot Tariff Act increases tariffs on Cuban sugar and reduces its share of the U.S. sugar market, exacerbating economic conditions on the island during the Great Depression.
1933: In May, the United States dispatches Ambassador Sumner Welles to mediate between the Machado government and the opposition. A general strike in August brings the crisis to a climax, with a military coup ousting Machado and installing Carlos Manuel de Céspedes y Quesada as provisional president. Machado leaves Cuba for The Bahamas and eventually dies in Miami in 1939. In September, the "Sergeants' Revolt," led by Fulgencio Batista, overthrows the Céspedes administration and helps to establish a new provisional government headed by Ramón Grau San Martín, which only lasts one hundred days.
1934: Batista overthrows the Grau San Martín government in January and briefly installs Carlos Hevia and Manuel Márquez Sterling as presidents, and later Carlos Mendieta. The United States abrogates the Platt Amendment in May as part of President Franklin D. Roosevelt's Good Neighbor Policy.
1940: Batista is elected president in July. A new Cuban Constitution, drafted under the presidency of Federico Laredo Brú, is implemented in October.
1944: After finishing his presidential term, Batista leaves Cuba for the United States, spending time in Daytona Beach, Florida, and New York City.
1948: During the winter season, Cuba attracts approximately 162,000 U.S. tourists. Between May and August, approximately 40,000 Cuban tourists visit Miami.
1952: On March 10, Batista (who had returned to Cuba to run again for president) deposes President Carlos Prío Socarrás, cancels the constitution, and suspends elections.
1953: On July 26, Fidel Castro leads an unsuccessful revolt against the Batista regime, attacking the Moncada army barracks in Santiago de Cuba. Fidel, his brother Raúl, and other Moncada survivors are imprisoned, but Batista grants them amnesty in May 1955. The Castro brothers go into exile in Mexico.
1956: Fidel Castro returns to eastern Cuba from Mexico and takes to the Sierra Maestra mountains where, aided by Ernesto "Che" Guevara, he wages a guerrilla war.
1957: 236,217 U.S. tourists visit Cuba.
1958: In March, Raúl Castro establishes guerrilla operations on a second front in the Sierra Cristal mountains in northern Oriente Province. In the same month, the United States imposes an arms embargo against the Batista government.
1959: Batista leaves Cuba with his closest associates on New Year's Eve. A general strike in early January forces the military government to relinquish power to the 26th of July Movement. On January 7, the United States recognizes the new Cuban government. Fidel Castro arrives in Havana on January 8. The following month, he is sworn in as prime minister. Castro visits the United States in April, but President Dwight D. Eisenhower refuses to meet with him. The Cuban government approves the first agrarian reform law in May, eradicating large privately owned landed estates.
1960: In July, the Cuban government begins to nationalize all U.S.-owned businesses on the island without compensation, including twenty-one sugar mills, utilities, and banks. In October, the Eisenhower administration imposes a partial trade embargo of Cuba, except for food and medicine. Operation Pedro Pan begins in December, bringing 14,048 unaccompanied Cuban children to the United States until the end of the operation in October 1962.
1961: The United States breaks diplomatic relations with Cuba in January. The Kennedy administration establishes the Cuban Refugee Program in February. In April, the Bay of Pigs (Playa Girón) Invasion, supported by the U.S. government, fails and 1,197 exiles are taken prisoner in Cuba. Fidel Castro declares that Cuba is a socialist state in May. In December, a new Cuban law nationalizes the private property of all Cubans fleeing the island.
1962: In January, the Organization of American States, led by the U.S. government, suspends Cuba from its membership because of its Marxist-Leninist government. In February, the Kennedy administration extends the U.S. embargo to all trade with Cuba. The Cuban Missile Crisis takes place in October, after the United States confirms that Fidel Castro allowed the Soviet Union to deploy nuclear missiles on the island. The crisis is resolved when the Soviet Union removes the missiles in return for the withdrawal of U.S. nuclear missiles from Turkey. Between January 1959 and October 1962, when all commercial flights between Havana and Miami are suspended, 248,070 persons flee the island for the United States. In December, 1,113 men taken prisoner at the Bay of Pigs Invasion are returned to the United States in exchange for food and medicine for Cuba.
1963: A second agrarian reform law centralizes most farms in the hands of the Cuban government.
1965: In September, Castro announces that any Cuban wishing to leave for the United States may do so through the port of Camarioca in Matanzas. A total of 2,979 Cubans travel by boat to the United States between October 10 and November 15. The boatlift leads to the establishment of an air bridge between Varadero and Miami, known as the "Freedom Flights" in the United States.
1966: The U.S. Congress approves the Cuban Adjustment Act, allowing Cubans who left the island after 1959 to be admitted for permanent residence in the United States. An estimated 300,000 Cuban refugees are living in the United States in 1966.
1968: The Cuban government carries out a "Revolutionary Offensive," nationalizing all remaining small private businesses, a total of 56,636 according to the state-owned newspaper Granma.
1973: The "Freedom Flights" end, after bringing 260,561 Cubans to the United States.
1976: A new Cuban Constitution, modeled after the 1936 Soviet Constitution, institutionalizes the socialist character of the Cuban government.
1977: The United States and Cuba establish limited diplomatic relations by opening interests sections in Washington and Havana.
1978: Seventy-five Cuban exiles meet with representatives of the Cuban government in Havana to negotiate the release of political prisoners, family reunification, and travel to the island.
1979: More than 100,000 exiles return to visit the island.
1980: In April, 10,856 Cubans storm the Peruvian Embassy in Havana requesting asylum. A few days later, Fidel Castro announces that all Cubans wishing to emigrate to the United States can do so through the port of Mariel, west of Havana. The Mariel boatlift results in the emigration of 125,266 Cubans to Florida before the port is closed in October.
1982: The U.S. Department of State adds Cuba to its list of state sponsors of terrorism because of the island government's support for revolutionary movements in Latin America and Africa.
1983: The armed U.S. intervention in Grenada results in the capture of 638 Cuban combatants.
1984: Cuba and the United States sign a wide-ranging immigration agreement, under which Cuba agrees to accept the return of 2,746 Mariel emigrants with criminal records, deemed "excludable aliens" by the United States. In turn, the United States agrees to admit up to 20,000 Cuban immigrants per year.
1985: The United States inaugurates Radio Martí broadcasts to Cuba to provide "uncensored news and information programming" to the people of the island. Havana responds by suspending the immigration agreement with the United States and family visits to Cuba.
1989: Ileana Ros-Lehtinen becomes the first Cuban American elected to the U.S. Congress.
1992: In February, the Cuban Constitution is amended, eliminating any mention of the former Soviet Union. The U.S. Congress enacts the Torricelli Bill (Cuban Democracy Act of 1992) in October, increasing trade sanctions against Cuba by prohibiting U.S. subsidiaries in third countries from trading with the island.
1993: The Cuban government legalizes the use of the U.S. dollar by Cuban citizens, along with the Cuban peso, thus beginning a dual currency system on the island.
1994: On August 12, Fidel Castro announces that his government will let those Cubans who want to leave the island do so in any way they can. Between August 13 and September 13, the U.S. Coast Guard detains 30,879 Cubans attempting to leave the island during the balsero (rafter) crisis. The rafters are sent to the U.S. naval base in Guantánamo Bay (and initially to Panama) before gaining entry into the United States. In September, Havana and Washington sign an agreement whereby the United States will issue 20,000 immigrant visas annually to Cubans, and in return Cuba pledges to control undocumented migration.
1995: President Bill Clinton announces that the U.S. Coast Guard will repatriate Cubans interdicted at sea, thus beginning the "wet foot / dry foot" policy. Cubans arriving on U.S. soil will be allowed to stay.
1996: In February, Cuban air force fighters shoot down two civilian aircraft flown by the Cuban exile group Brothers to the Rescue. In March, President Clinton enacts the Helms-Burton Bill ("Cuban Liberty and Democratic Solidarity Act") into law.
1998: Pope John Paul II visits Cuba and calls for an end to the U.S. embargo against Cuba, proclaiming, "Let Cuba open itself to the world and the world open itself to Cuba."
1999: In February, Cuba's National Assembly enacts Law No. 88 for the "Protection of the National Independence and Economy of Cuba," imposing terms of imprisonment for aiding the "anti-Cuban" policies of the U.S. government. Five-year-old rafter Elián González arrives in Miami in November.
2000: In June, Elián González returns to Cuba with his father after a prolonged international custody battle. In October, the U.S. government authorizes the sale of food and medicine to Cuba for the first time in nearly forty years.
2001: Five Cuban intelligence officers are convicted of twenty-six counts of spying, conspiring to commit murder, and other illegal activities in the United States.
2002: Former President Jimmy Carter is the first former U.S. president to visit Cuba since 1959.
2004: In June, the George W. Bush administration imposes new restrictions on U.S. travel to Cuba, including reduced Cuban American family visits and remittances to the island. In October, the Castro government bans transactions in U.S. dollars and imposes a 10 percent tax on dollar-peso conversions.
2006: Fidel Castro undergoes emergency intestinal surgery and temporarily hands over power to his brother Raúl.
2008: Cuba's National Assembly elects Raúl Castro president.
2009: In September, President Barack Obama lifts U.S. government restrictions on family travel and remittances to Cuba. In December, U.S. government subcontractor Alan Gross is detained in Cuba, accused of crimes against the Cuban government.
2011: The Obama administration reinstates permits for U.S. citizens to travel to Cuba for cultural and educational exchanges, increasing "people-to-people" contacts with the island.
2013: The Cuban government enacts immigration and travel reforms, eliminating the requirement of a letter of invitation from abroad, extending the maximum period of residence for Cuban citizens abroad to two years, and issuing passports to prominent dissidents who travel to the United States and other countries.
2014: On December 17, the Cuban government releases Alan Gross from prison for "humanitarian reasons." At the same time, three Cubans convicted as spies in the United States are exchanged for a U.S. intelligence agent imprisoned in Cuba. President Obama announces major changes in U.S. policy toward Cuba, including taking steps toward reestablishing diplomatic relations, reviewing Cuba's designation as a state sponsor of terrorism, and facilitating certain types of trade and travel by U.S. citizens to the island.
2015: In May, President Obama removes Cuba from the State Department's list of state sponsors of terrorism. In July, the United States and Cuba restore diplomatic relations and open embassies in their respective capitals. The United States and Cuba reestablish direct mail service as part of a pilot program in December.
2016: In March, President Obama is the first sitting U.S. president since 1928 to visit Cuba. The first commercial flights between the United States and Cuba since 1962 are reinstated in August. In November, Raúl Castro announces the death of his brother Fidel at age ninety.
2017: Outgoing President Obama announces the end of the "wet foot / dry foot policy" in January. In June, President Donald Trump proclaims changes to U.S. policy toward Cuba, including prohibiting U.S. business transactions with Cuban state enterprises run by the military and restricting individual people-to-people travel to the island. In September, the State Department orders the departure of non-emergency personnel assigned to the U.S. Embassy in Havana in response to a series of "sonic attacks" against twenty-four employees of the embassy. The United States expels fifteen diplomats from the Cuban Embassy in Washington, D.C., in October. According to the Cuban government, 618,346 residents of the United States visit Cuba by the end of the year.
2018: In March, the U.S. Department of State announces that the U.S. Embassy in Havana will continue to operate with the minimum personnel required to perform core diplomatic and consular functions. The National Assembly of People's Power selects Miguel Díaz-Canel as president of Cuba in April, but Raúl Castro remains first secretary of the Cuban Communist Party. The Cuban government releases the draft of a new constitution in July and calls for a public debate about the proposed amendments between August and November. After reviewing the comments and suggestions made by the island's population and its citizens living abroad, the National Assembly approves a second draft of the constitutional text in December.
2019: In February, nearly eighty-seven percent of Cuba's electorate ratifies a new constitution, which reaffirms the "irrevocable" character of socialism, the "vanguard" and leading role of the Cuban Communist Party, and the prevalence of a centrally planned economy over the market. The Trump administration implements Title III of the Helms-Burton Act in April, allowing U.S. citizens to sue companies that use properties confiscated by the Cuban government after 1959. In June, the Trump administration ends the group "people-to-people" authorization for U.S. travelers and prohibits cruise ships and other passenger vessels from traveling to Cuba. The administration also limits the allowable amount of family remittances to Cuba to $1,000 per quarter. In October, the Trump administration bans most U.S. commercial flights to Cuba, except those bound for Havana.
2020: In January, the Trump administration cancels U.S. charter flights to nine airports in Cuba, leaving Havana as the sole destination. In March, the Cuban government suspends entry into the country by non-Cubans as a preventive measure against the spread of COVID-19. Cuba begins to send health personnel to several countries affected by the coronavirus pandemic, while the United States warns those countries that they should put an end to Cuba's labor abuses, classifying them as a form of "modern slavery." In July, the Cuban government announces that it will allow the use of U.S. dollars in some government-run stores and eliminate a 10 percent tax on U.S. dollars. In October, the U.S. government prohibits remittances to Cuba through companies controlled by the Cuban military, including Fincimex. Because of these sanctions, Western Union closes its 407 money transfer locations across Cuba in November.
2021: The outgoing Trump administration reinstates Cuba to the U.S. State Department's list of state sponsors of terrorism in January, mainly because the Cuban government refuses to extradite ten leaders of Colombia's National Liberation Army. On July 11, thousands of Cubans take to the streets to protest the scarcity of food, medicine, fuel, and other essential items on the island, as well as to demand freedom and criticize the communist government. The Biden administration expresses its support of people's right to demonstrate peacefully and condemns the Cuban government's violent response to the protests. In November, the Nicaraguan government eliminates the visa requirement for Cubans, facilitating emigration from the island to the U.S. southern border with Mexico.
2022: In March, the U.S. Embassy in Havana announces that it will gradually increase staffing for its consular section, to partially restore the processing of U.S. visas for Cuban citizens. U.S. and Cuban officials meet in Washington in April to discuss migration, the first such talk between the two countries since 2018. In May, the Biden administration relaxes some restrictions on travel and remittances to Cuba, including reinstating the Cuban Family Reunification Parole Program, restoring U.S. flights to airports other than Havana, and removing the $1,000 quarterly limit on family remittances. The U.S. Embassy in Havana announces in September that it will resume full immigrant visa processing for the first time since 2017. In October, U.S. Customs and Border Protection reports that 224,607 unauthorized citizens of Cuba had been apprehended and/or expelled trying to enter the United States during fiscal year 2022, which began in October 2021 and ended in September 2022. In November, U.S. and Cuban officials meet in Havana to discuss the implementation of the U.S.-Cuba migration accords.
2023: In January, the U.S. Embassy in Havana resumes full immigrant visa processing for the first time since 2017. The White House announces new enforcement measures to increase security at the U.S.-Mexico border, including deporting unauthorized migrants to Mexico and expanding the parole process to citizens of Cuba, Haiti, and Nicaragua. Also in January, the Biden administration sends a delegation to Havana to restart U.S.-Cuba talks on law-enforcement issues that were halted under former President Trump. At the same time, Western Union reestablishes remittance service between the United States and Cuba through 343 entities in Florida, after more than two years of its suspension by the Trump administration. In March, the company extends its service to its entire network in the United States, including more than 4,400 retail locations in the continental U.S. and Puerto Rico. In April, the U.S. and Cuban governments hold a new round of migration talks in Washington. In May, the Cuban government announces changes to its passport regulations, such as extending their validity from six to ten years and reducing their cost. In fiscal year 2023, which ended in September, U.S. Customs and Border Protection reports it had encountered 200,287 Cuban citizens trying to cross the U.S. border illegally. In addition, between January and December 2023, more than 74,000 Cubans travel to the United States under the humanitarian parole program announced earlier by the Biden administration.
2024: In February, the U.S.-Cuba Trade and Economic Council reports that Cuba had imported $342.6 million in food and agricultural products from the United States in 2023, an increase of 12.4 percent compared to 2021. In May, the U.S. Treasury Department announces measures to promote independent private businesses in Cuba, including allowing entrepreneurs on the island to open, maintain, and remotely access U.S. bank accounts, as well as expanding internet access on the island. In August, the U.S. Embassy in Havana announces that it will resume processing of nonimmigrant visas, which had been suspended since 2017. U.S. Customs and Border Protection reports that it encountered 217,615 Cuban citizens trying to cross into the United States without authorization between October 2023 and September 2024. In October, the Biden administration announces that it will not renew the humanitarian parole program for migrants from Cuba, Venezuela, Nicaragua, and Haiti.