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.

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

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.

Cuba's oldest museum was founded in 1899 by Emilio Bacardí Moreau, the former Santiago mayor whose rum-making family fled to Puerto Rico after the Revolution. It is just a few metres from the Parque Céspedes, in the heart of the city. The museum has an excellent collection of Cuban art, as well as some European works, some items from the wars of independence and an archaeological hall that features a 3,000-year-old Egyptian mummy, two Peruvian skeletons and a shrunken head. It houses the most important painting gallery in Cuba, displaying an enviable collection of colonial painting dating back two centuries.