The Spanish fortress known as El Morro, south of Santiago, was constructed between 1638 and 1700 and was designed by Giovanni Antonelli, the Italian architect and engineer responsible for fortresses bearing the same name in both Havana and San Juan, Puerto Rico. El Morro was built to ward off pirates (and rebuilt after a 1662 attack by the English pirate Henry Morgan). Today, its solid walls house the Museum of Piracy, its rooms also reflects the main events connected with the naval battle of Santiago de Cuba, episode of the Spanish-Cuban-American in 1898 and photographs related to the events of Maine , the Spanish and U.S. military leaders, Admiral Pascual Cervera and Vice Admiral Sampson and planes and coastal defenses and batteries of El Morro. There are wonderful views from interior rooms, which have wooden floors and stone walls, as well as from various terraces.

This Spanish-colonial mansion was the birthplace of poet José María Heredia, who, because of his pro-independence writings, is considered Cuba's first national poet. Heredia died in 1839 at age 36 while exiled in Mexico. The house, now just a fraction of its original size, displays period furniture and some of the poet's works and belongings. The home's traditional interior patio is planted with trees and plants—including orange, myrtle, palm, and jasmine—associated with Heredia's verse. A marble plaque on the house's Calle Heredia facade excerpts one of the poet's most famous works, "Niágara".

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.

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.