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.

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.