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.

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.

Every night, the Tropicana cabaret offers its performance "Viaje al Caribe" (a Journey to the Caribbean), which narrates the history of the people of Santiago, the most Caribbean city in Cuba, where one can feel the influence of Haiti and its voodoo religion and French customs, Dominican Republic and its merengue, Jamaica and its reggae and Puerto Rico among others. Dinner and show in the same style as the famous Tropicana Cabaret from Havana. This modern facility has been elegantly decorated with traditional elements that blend-in with the lush natural vegetation surrounding the area

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.