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 most atmospheric part of the city is Old Santiago. Céspedes Park constitutes the political, religious, administrative and social center more important of the city. The attractive square is a genteel place with tall trees, gas lanterns and iron benches. In their perimeter were located by disposition of the Laws of Indias, the representative buildings of the power: Town Hall, Cathedral, the house of the governors and the mansions of the main families of the village. Parque Céspedes is dominated by its twin-towered cathedral. A basilica was built on this spot in 1528, but what you see was rebuilt in the early 19th century after a series of earthquakes and fires.

This is undoubtedly one of the city's most well-known streets. It offers an excellent natural viewing point and is the only stepped street in Cuba. It's part of the Tivoli neighborhood, where 18th-century French-colonial mansions sit side by side with 16th-century structures

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.