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.

In Tivolí you’ll find the famous Padre Pico steps, named for a Santiaguero priest who aided the city’s poor. Fidel Castro once roared fire and brimstone down on the Batista government here, but today you’ll find more pacific chess and domino players who have set up all-hours tables on the steps.

The museum of the Clandestine Struggle is located Padre Pico steps up. This excellent museum, in one of the city’s finest colonial houses, focuses on the activities of the resistance movement under local martyr Frank País. Residents of Santiago were instrumental in supporting the Revolution, as were peasants in the Sierra Maestra. From the museum’s balcony, there are tremendous views of Santiago and the bay.

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.