Cuba's oldest museum was founded in 1899 by Emilio Bacardí Moreau, the former Santiago mayor whose rum-making family fled to Puerto Rico after the Revolution. It is just a few metres from the Parque Céspedes, in the heart of the city. The museum has an excellent collection of Cuban art, as well as some European works, some items from the wars of independence and an archaeological hall that features a 3,000-year-old Egyptian mummy, two Peruvian skeletons and a shrunken head. It houses the most important painting gallery in Cuba, displaying an enviable collection of colonial painting dating back two centuries.

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 ceramic-tiled terrace is all that remains of a fort once used by authorities to monitor boat traffic. It's a great place to linger while taking in views of both the city and the bay. Music shows and other events are often held here, particularly on weekend evenings.

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".