Beautiful, heady SANTIAGO DE CUBA is the crown jewel of Oriente. Nowhere outside Havana is there a city with such definite character or such determination to have a good time. Spanning out from the base of a deep-water bay and cradled by mountains, Santiago is credited with being the most Caribbean part of Cuba, a claim borne out by its laidback lifestyle and rich mix of inhabitants. It was here that the first slaves arrived from West Africa, and today Santiago boasts a larger percentage of black people than anywhere else in Cuba. Afro-Cuban culture, with its music, myths and rituals, has its roots here, with later additions brought by French coffee planters fleeing revolution in Haiti in the eighteenth century.

The leisurely pace of life doesn’t make for a quiet city, however, with the higgledy-piggledy net of narrow streets around the colonial quarter ringing night and day with the beat of drums and the toot of horns. Music is a vital element of Santiaguero life, whether heard at the country’s most famous Casa de la Trova and the city’s various other venues, or at the impromptu gatherings that tend to reach a crescendo around carnival in July. As well as being the liveliest, the summer months are also the hottest – the mountains surrounding the city act as a windbreak and the lack of breeze means that Santiago is often several degrees hotter than Havana, and almost unbearably humid.

Although Santiago’s music scene and carnival are good enough reasons to visit, there are a host of more concrete attractions. Diego Velázquez’s sixteenth-century merchant house and the elegant governor’s residence, both around Parque Céspedes in the colonial heart of town, and the commanding El Morro castle at the entrance to the bay, exemplify the city’s prominent role in Cuban history. Additionally, the part played by townsfolk in the revolutionary struggle, detailed in several fascinating museums, makes Santiago an important stop on the Revolution trail.

One downside to a visit here is street hustle in the downtown area. Begging and being propositioned is an unbearable problem, especially in and around Parque Céspedes. The level and persistence of hassle is worse than in any other Cuban city – and women travelling on their own, in particular, need to grit their teeth.

Brief history

Established by Diego Velázquez de Cuéllar in 1515, the port of Santiago de Cuba was one of the original seven villas founded in Cuba. Velázquez, pleased to find so excellent a natural port near to reported sources of gold (which were quickly exhausted), named the port Santiago (St James) after the patron saint of Spain. With the construction of the central trading house shortly afterwards, the settlement became Cuba’s capital.

After this auspicious start – boosted by the discovery of a rich vein of copper in the foothills in nearby El Cobre – the city’s importance dwindled somewhat. Buffeted by severe earthquakes and pirate attacks, Santiago developed more slowly than its western rival and in 1553 was effectively ousted as capital when the governor of Cuba, Gonzalo Pérez de Angulo, moved his office to Havana.

Sugar, coffee and slaves

Santiago’s physical bounty led to a new boom in the eighteenth century, when Creoles from other areas of the country poured sugar wealth into the area by developing plantations. The cool mountain slopes around Santiago proved ideal for growing coffee, and French planters, accompanied by their slaves, emigrated here after the 1791 revolution in Haiti, bringing with them a cosmopolitan air and continental elegance, as well as a culturally complex slave culture.

Relations with Havana had always been frosty, especially as culturally distinct Santiago had fewer Spanish-born Penínsulares, who made up the ruling elite. This rivalry boiled over during the Wars of Independence, which were led by the people of Oriente. Much of the fighting between 1868 and 1898 took place around Santiago, led in part by the city’s most celebrated son, Antonio Maceo.

The US takeover

The Cuban army had almost gained control of Santiago when, in 1898, the United States intervened. Eager to gain control of the imminent republic, it usurped victory from the Cubans by securing Santiago and subsequently forcing Spanish surrender after a dramatic battle on Loma de San Juan. The Cubans were not even signatories to the resultant Paris peace settlement between the US and Spain, and all residents of Santiago province were made subject to the protection and authority of the US. As an added insult, the rebel army that had fought for independence for thirty years was not even allowed to enter Santiago city.

The Revolution and Santiago today

Over the following decades, the American betrayal nourished local anger and resentment, and by the 1950s Santiago’s citizens were playing a prime role in the civil uprisings against the US-backed president Fulgencio Batista. Assured of general support, Fidel Castro chose Santiago for his debut battle in 1953, when he and a small band of rebels attacked the Moncada barracks. Further support for their rebel army was later given by the M-26–7 underground movement that was spearheaded in Santiago by Frank and Josue País. It was in Santiago’s courtrooms that Fidel Castro and the other rebels were subsequently tried and imprisoned.

When the victorious Castro swept down from the mountains, it was in Santiago that he chose to deliver his maiden speech, in the first week of January 1959. The city, which now carries the title “Hero City of the Republic of Cuba”, is still seen – especially in Havana – as home to the most zealous revolutionaries, and support for the Revolution is certainly stronger here than in the west. The rift between east and west still manifests itself today in various prejudices, with Habaneros viewing their eastern neighbours as troublemaking criminals, and considered as solipsistic and unfriendly by Santiagueros in return.

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