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.

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.

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 is one of the continent's oldest cathedrals, the seat of the fourth bishopric of America, although the building that it currently occupies was built in 1922, thus reflecting the eclectic style of architecture. One of its sides houses the Ecclesiastical Museum, with a valuable collection of furniture, paintings and sacred artefacts