Some eighteen thousand Saint Dominican refugees, both ethnic French whites and free people of color, and African freedmen, came from Saint-Domingue in the summer of 1803 during the last days of the Haitian slave revolt, which had started in 1791.

The immigrants, who included freedmen as France had abolished slavery on Saint-Domingue, struggled to maintain their freedom in Cuba, which was still a slave society.

Near the end of the century, during the Spanish–American War, Santiago was the site of the major defeat of Spanish troops at San Juan Hill on 1 July 1898.

[8] Spain later surrendered to the United States after Admiral William T. Sampson destroyed the Spanish Atlantic fleet just outside Santiago's harbor on 3 July 1898.

[citation needed] José Martí, a Cuban poet, writer, and national hero, is buried in Santa Ifigenia Cemetery in this city.

On 26 July 1953, the Cuban Revolution began with an ill-prepared armed attack on the Moncada Barracks by a small contingent of rebels led by Fidel Castro.

Shortly after this disastrous incident, País began talking with students and young working people informally, drawing around him what became an extremely effective urban revolutionary alliance.

He and his followers developed highly organized cells, coordinating a large-scale urban resistance that became instrumental in the success of the Cuban Revolution.

They published a cheap newsletter that reported news critical of the government, attempting to counter Batista's censorship of the mainline press.

On 1 January 1959, Fidel Castro proclaimed the victory of the Cuban Revolution from a balcony on Santiago de Cuba's city hall.

The mural relief portrait on the building façade depicts Juan Almeida Bosque, a commander of insurgent forces in the Cuban Revolution.

Some of Cuba's most famous musicians, including Compay Segundo, Ibrahim Ferrer and Eliades Ochoa (all of whom participated in the film Buena Vista Social Club) and trova composer Ñico Saquito (Benito Antonio Fernández Ortiz) were born in the city or in one of the villages surrounding it.

Many colonial buildings have huge windows and balconies, where people can enjoy views of the steep streets and wooded hills.

The local citadel of San Pedro de la Roca is inscribed on the UNESCO World Heritage List as "the most complete, best-preserved example of Spanish-American military architecture, based on Italian and Renaissance design principles".

[15] Omnibus Metropolitanos (OM) connects the adjacent towns and municipalities in the metropolitan area with the city center, with a maximum distance of 40 km (25 mi).

[citation needed] The city of Santiago is also crossed by the Carretera Central highway and by the southern section of the A1 motorway, largely unbuilt, that will link it with Havana when it is completed.