Santiago was Cuba's first capital, the beachhead of the conquest, the port Spain fortified against pirates, and the city where both wars of independence and the 1953 revolt began. Three days trace 500 years, from Velázquez's mudéjar balcony to Martí's mausoleum.
Built 1516-1530 for Cuba's first governor, the oldest surviving house in the Americas hides Moorish mudéjar screens, a ground-floor gold smelting furnace and 16 rooms of colonial furniture. Open Tue-Sun 9:00-17:00.
The 1803 birthplace of José María Heredia, the Romantic poet exiled at twenty for plotting independence, keeps its shaded courtyard, tinajón water jars and early editions of the ode Cuban schoolchildren still recite.
Battista Antonelli's 1638 clifftop fortress guarding the bay mouth, UNESCO-listed since 1997, with drawbridge, dungeons, gun batteries and a piracy museum recalling raids by Jacques de Sores and Henry Morgan.
A brick terrace built on a 16th-century Spanish gun platform, looking down over the tiled roofs of Tivolí to the bay mouth where Cervera's fleet sailed out to destruction on 3 July 1898. Open daily, no ticket.
Founded in 1868, Santiago's necropolis holds José Martí's hexagonal mausoleum, Fidel Castro's plain granite boulder marked only FIDEL, Carlos Manuel de Céspedes, Compay Segundo and the Bacardí family vault.
Alberto Lescay's 1991 monument sets the mambí general on horseback among 23 steel machetes thrusting from the ground — one for 23 March 1878, when Maceo's men resumed a war the rest of Cuba had just ended.
The bullet-pocked red-and-white farmhouse rented as cover, from which 135 rebels drove off at dawn on 26 July 1953 to attack Moncada. The weapons well, the uniforms and the original cars are all still here.
The ridge where the Rough Riders and the Buffalo Soldiers stormed Spanish blockhouses on 1 July 1898. A peace tree, rival Spanish and American memorials and a mambí monument mark where an empire ended.
A yellow colonial mansion on the crest of Tivolí, the police headquarters that Frank País's underground burned on 30 November 1956. Four rooms hold their clandestine printing presses, homemade bombs and País's shirt.
The modest house at Los Maceos 207 where the Bronze Titan was born in 1845 to a free mulatto farmer. His mother Mariana Grajales swore her nine sons to independence here before they rode out in the 1868 uprising.
Cuba's oldest museum, founded in 1899 by the rum heir and independence veteran who became Santiago's first mayor: mambí machetes, slave shackles and punishment stocks, colonial painting and a genuine Egyptian mummy.
The stone staircase cut into the hill settled by French planters who fled Haiti's revolution after 1791. Student rebels fought police on these steps in the 1950s, and the streets below still follow the French colonial grid.