The Spanish fortress known as El Morro, south of Santiago, was constructed between 1638 and 1700 and was designed by Giovanni Antonelli, the Italian architect and engineer responsible for fortresses bearing the same name in both Havana and San Juan, Puerto Rico. El Morro was built to ward off pirates (and rebuilt after a 1662 attack by the English pirate Henry Morgan). Today, its solid walls house the Museum of Piracy, its rooms also reflects the main events connected with the naval battle of Santiago de Cuba, episode of the Spanish-Cuban-American in 1898 and photographs related to the events of Maine , the Spanish and U.S. military leaders, Admiral Pascual Cervera and Vice Admiral Sampson and planes and coastal defenses and batteries of El Morro. There are wonderful views from interior rooms, which have wooden floors and stone walls, as well as from various terraces.

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

This venue is one of the symbols of Santiago de Cuba, where traditional rhythms such as the trova, bolero and son were born. Situated very close to the Parque Céspedes, it is the meeting place for 'trovadores', both old and new. Considered one of the most important cultural institutions in Cuba, it preserves a musical movement that is deeply-rooted in the traditions of Santiago and forms an integral part of the city's life.