Travel, financial and commercial transactions by United States citizens to Cuba are made illegal by the John F. Kennedy administration.

John Fitzgerald Kennedy (May 29, 1917 November 22, 1963), often referred to by his initials as JFK or by the nickname Jack, was an American politician who served as the 35th president of the United States from 1961 until his assassination near the end of his third year in office. Kennedy was the youngest person to assume the presidency by election. He was also the youngest president at the end of his tenure, and his lifespan was the shortest of any president. Kennedy served at the height of the Cold War, and the majority of his work as president concerned relations with the Soviet Union and Cuba. A Democrat, he represented Massachusetts in both houses of the U.S. Congress prior to his presidency.

Born into the prominent Kennedy family in Brookline, Massachusetts, Kennedy graduated from Harvard University in 1940 before joining the U.S. Naval Reserve the following year. During World War II, he commanded a series of PT boats in the Pacific theater. Kennedy's survival of the sinking of PT-109 and rescue of his fellow sailors made him a war hero for which he earned the Navy and Marine Corps Medal, but left him with serious injuries. After a brief stint in journalism, Kennedy represented a working-class Boston district in the U.S. House of Representatives from 1947 to 1953. He was subsequently elected to the U.S. Senate and served as the junior senator for Massachusetts from 1953 to 1960. While in the Senate, Kennedy published his book, Profiles in Courage, which won a Pulitzer Prize. In the 1960 presidential election, he narrowly defeated Republican opponent Richard Nixon, who was the incumbent vice president. Kennedy's humor, charm, and youth in addition to his father's money and contacts were great assets in his campaign. Kennedy's campaign gained momentum after the first televised presidential debates in American history. He was the first Catholic elected president.

Kennedy's administration included high tensions with communist states in the Cold War. As a result, he increased the number of American military advisers in South Vietnam. The Strategic Hamlet Program began in Vietnam during his presidency. In April 1961, he authorized an attempt to overthrow the Cuban government of Fidel Castro in the failed Bay of Pigs Invasion. In November 1961, he authorized the Operation Mongoose, also aimed at removing the communists from power in Cuba. He rejected Operation Northwoods in March 1962, but his administration continued to plan for an invasion of Cuba in the summer of 1962. The following October, U.S. spy planes discovered Soviet missile bases had been deployed in Cuba; the resulting period of tensions, termed the Cuban Missile Crisis, nearly resulted in the breakout of a global thermonuclear conflict. He also signed the first nuclear weapons treaty in October 1963. Kennedy presided over the establishment of the Peace Corps, Alliance for Progress with Latin America, and the continuation of the Apollo program with the goal of landing a man on the Moon before 1970. He also supported the civil rights movement but was only somewhat successful in passing his New Frontier domestic policies.

On November 22, 1963, he was assassinated in Dallas. Lyndon B. Johnson, the vice president, assumed the presidency upon Kennedy's death. Lee Harvey Oswald, a former U.S. Marine, was arrested for the assassination, but he was shot and killed by Jack Ruby two days later. The FBI and the Warren Commission both concluded Oswald had acted alone. After Kennedy's death, Congress enacted many of his proposals, including the Civil Rights Act of 1964 and the Revenue Act of 1964. Despite his truncated presidency, Kennedy ranks highly in polls of U.S. presidents with historians and the general public. His personal life has also been the focus of considerable sustained interest following public revelations in the 1970s of his chronic health ailments and extramarital affairs. Kennedy is the most recent U.S. president to have died in office.

Cuba ( (listen) KEW-bə, Spanish: [ˈkuβa] (listen)), officially the Republic of Cuba (Spanish: República de Cuba [reˈpuβlika ðe ˈkuβa] (listen)), is a country comprising the island of Cuba, as well as Isla de la Juventud and several minor archipelagos. Cuba is located where the northern Caribbean Sea, Gulf of Mexico, and Atlantic Ocean meet. Cuba is located at the east of the Yucatán Peninsula (Mexico), south of both the American state of Florida and the Bahamas, west of Hispaniola (Haiti/Dominican Republic), and north of both Jamaica and the Cayman Islands. Havana is the largest city and capital; other major cities include Santiago de Cuba and Camagüey. The official area of the Republic of Cuba is 109,884 km2 (42,426 sq mi) (without the territorial waters). The main island of Cuba is the largest island in Cuba and in the Caribbean, with an area of 104,556 km2 (40,369 sq mi). Cuba is the second-most populous country in the Caribbean after Haiti, with over 11 million inhabitants.The territory that is now Cuba was inhabited by the Ciboney Taíno people from the 4th millennium BC until Spanish colonization in the 15th century. From the 15th century, it was a colony of Spain until the Spanish–American War of 1898, when Cuba was occupied by the United States and gained nominal independence as a de facto United States protectorate in 1902. As a fragile republic, in 1940 Cuba attempted to strengthen its democratic system, but mounting political radicalization and social strife culminated in a coup and subsequent dictatorship under Fulgencio Batista in 1952. Open corruption and oppression under Batista's rule led to his ousting in January 1959 by the 26th of July Movement, which afterwards established communist rule under the leadership of Fidel Castro. Since 1965, the state has been governed by the Communist Party of Cuba. The country was a point of contention during the Cold War between the Soviet Union and the United States, and a nuclear war nearly broke out during the Cuban Missile Crisis of 1962. Cuba is one of a few extant Marxist–Leninist socialist states, where the role of the vanguard Communist Party is enshrined in the Constitution. Under Castro, Cuba was involved in a broad range of military and humanitarian activities throughout both Africa and Asia.Culturally, Cuba is considered part of Latin America. It is a multiethnic country whose people, culture and customs derive from diverse origins, including the Taíno Ciboney peoples, the long period of Spanish colonialism, the introduction of enslaved Africans and a close relationship with the Soviet Union in the Cold War.

Cuba is a founding member of the United Nations, the G77, the Non-Aligned Movement, the Organisation of African, Caribbean and Pacific States, ALBA and the Organization of American States. It has currently one of the world's only planned economies, and its economy is dominated by the tourism industry and the exports of skilled labor, sugar, tobacco, and coffee. Cuba has historically – both before and during Communist rule – performed better than other countries in the region on several socioeconomic indicators, such as literacy, infant mortality and life expectancy.Cuba has a single-party authoritarian regime where political opposition is not permitted. There are elections in Cuba, but they are not considered democratic. Censorship of information (including limits to internet access) is extensive, and independent journalism is repressed in Cuba; Reporters Without Borders has characterized Cuba as one of the worst countries in the world for press freedom.