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.

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.

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.

This venue is one of the symbols of Santiago de Cuba, where traditional rhythms such as the trova, bolero and son were born. Situated very close to the Parque Céspedes, it is the meeting place for 'trovadores', both old and new. Considered one of the most important cultural institutions in Cuba, it preserves a musical movement that is deeply-rooted in the traditions of Santiago and forms an integral part of the city's life.