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 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

This museum is located in the former Moncada Barracks, a military fortification which came under attack on 26 July 1953 by a group of young revolutionaries led by Fidel Castro Ruz. Moncada was the second military fort of the country, occupied by about a thousand men under the command of Fulgencio Batista. Unfortunately, the rebels were either killed or captured. Although unsuccessful, the attack ignited the sparks of Cuban Revolution. Fidel wrote his famous speech "La historia me absolverá" ("History will absolve me"), which was smuggled out of prison, printed, and distributed throughout the island. This event launched the final stage of the struggle for the country's freedom. After the victory of the revolution Moncada Barrack was transformed into a school, and a space was devoted to Museum. The museum exhibits some of the revolutionaries' personal belongings, some of the weaponry used and photographs of the historical event, as well as a valuable coin collection.