One of Santiago’s most delightful people-watching spots is Plaza Dolores, a shady plaza lined with colonial-era homes (several now house restaurants). Avenida José A. Saco (more commonly known as Enramada) is Santiago’s main shopping thoroughfare. Its faded 1950s neon signs and ostentatious buildings recall more prosperous times. Cobbled Calle Bartolomé Masó (also known as San Basilio), just behind Heredia and the cathedral, is a delightful street that leads down to the picturesque Tivolí district.

The spirit of one of the Caribbean's most vibrant street parties, Santiago's annual July carnival, is recalled in photos and newspaper clippings, floats, costumes, and musical instruments. Late afternoons here give a better sense of what carnival is like; stop by at 4 pm Tuesday through Saturday for a performance by music and dance troupes. The short spectacle of colorful costume, Afro-Cuban rhythms, and stirring song might have you planning your next trip to coincide with the main event. 

Visit San Juan Historic Park, a place where it was developed an important battle of the North American-Cuban-Hispanic War, bringing the end to an era. At the helm of a brigade at this battle was a future president of the United States, Theodore Roosevelt. The Peace Tree (Árbol de la Paz) is the tree in which it was signed the surrender of Santiago de Cuba. In the San Juan Hill you can admire various monuments in memory of the numbered casualties in both sides in the battle developed in the surroundings of Santiago on the first of July 1898. You can witness sculptures to the Victorious Mambí, to the Unknown North American Soldier and to the Spaniard Soldier surrounded by a series of cannons and artillery objects decorating the place. This is the only place in Cuba with a monument to the American soldier. Furthermore, quite close to the hill, a ceiba tree named the Peace Tree (Árbol de la Paz) witnessed the surrender of the city, although nowadays just remains the trunk of this historic tree which fell few months after the centenary of the battle.    

This museum is located in the former Moncada Barracks, a military fortification which came under attack on 26 July 1953 by a group of young revolutionaries led by Fidel Castro Ruz. Moncada was the second military fort of the country, occupied by about a thousand men under the command of Fulgencio Batista. Unfortunately, the rebels were either killed or captured. Although unsuccessful, the attack ignited the sparks of Cuban Revolution. Fidel wrote his famous speech "La historia me absolverá" ("History will absolve me"), which was smuggled out of prison, printed, and distributed throughout the island. This event launched the final stage of the struggle for the country's freedom. After the victory of the revolution Moncada Barrack was transformed into a school, and a space was devoted to Museum. The museum exhibits some of the revolutionaries' personal belongings, some of the weaponry used and photographs of the historical event, as well as a valuable coin collection.