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 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".

This is one of the continent's oldest cathedrals, the seat of the fourth bishopric of America, although the building that it currently occupies was built in 1922, thus reflecting the eclectic style of architecture. One of its sides houses the Ecclesiastical Museum, with a valuable collection of furniture, paintings and sacred artefacts

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.