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.

Abel Santamaría Historic Park is compounded by the museum, a library and a monument in the place in which you will find the ruins of the Former Saturnino Lora Civil Hospital. The museum of the enclosure which binds together all these buildings was opened in 1973 on the occasion of the 20th anniversary of the assault to the Moncada Headquarters, and exhibits the history related to the famous assault and the trial of Fidel Castro. The monument opened in 1979 in memory of Abel Santamaría and his colleagues who were tortured and murdered after the failed raising. It has four faces in which there is a sphinx of José Martí, another of Abel Santamaría, six bayonets symbolizing justice; the solitary star and a verse of the National Anthem. The water curtain which seems to support the compound symbolizes the ideals of the young men of the Centenary Generation.

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.

Constructed in 1516, this structure is reputed to be Cuba's oldest house one of the oldest in the Americas, although many historians now doubt that claim. Noticeable for its black-slatted balconies, it is one of Santiago's top attractions. Diego Velázquez, the Spanish conquistador who founded the city and was the island's first governor, lived upstairs. At the moment this old house works as Cuban Historical Colonial Environment's Museum, its rooms overflow with period furniture and carved woodwork and encircle­ two lovely courtyards. Inside you'll find period beds, desks, chests, and other furniture. On the first floor is a gold foundry. Memorable are the star-shape Moorish carvings on the wooden windows and balconies, and the original interior patio with its well and rain-collecting tinajón vessel. An adjacent house is filled with antiques intended to convey the French and English decorative and architectural influences—such as the radial stained glass above the courtyard doors—in the late 19th-century.