The most atmospheric part of the city is Old Santiago. Céspedes Park constitutes the political, religious, administrative and social center more important of the city. The attractive square is a genteel place with tall trees, gas lanterns and iron benches. In their perimeter were located by disposition of the Laws of Indias, the representative buildings of the power: Town Hall, Cathedral, the house of the governors and the mansions of the main families of the village. Parque Céspedes is dominated by its twin-towered cathedral. A basilica was built on this spot in 1528, but what you see was rebuilt in the early 19th century after a series of earthquakes and fires.

The Basilica of Our Lady of Charity of El Cobre, the Patron Saint of Cuba, can be found 27 km from the city centre, in a mining town founded in 1830. The Basilica stands on a gentle hill and contains display cases with items such as the medal received by the writer Ernest Hemingway on being awarded the Nobel Prize for Literature in 1954. The story of the Virgin dates from the early 1600s, when three men in a boat first saw her floating on water during a storm; tradition holds that the Virgin saved the men from certain drowning. Records show that the statue was most likely brought from Spain on order of the then-governor of Cuba, but don't play iconoclast with the millions of faithful who take seriously the Virgin's reputed miraculous powers. Our Lady of Charity of El Cobre was crowned by Pope John Paul II in 1998, during his visit to Cuba. Every 8th of September, her feast day, thousands of pilgrims come here to give thanks and beg favours of the blessed virgin.

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".