Where the narrow mouth of Santiago de Cuba's bay meets the open Caribbean, a castle climbs the headland in terraces of stone. San Pedro de la Roca, often called simply El Morro, was designed in the seventeenth century by the Italian military engineer Giovanni Battista Antonelli, from a family that built defences across the Spanish Caribbean. It was meant to shut the door on the pirates and privateers who had sacked Santiago more than once, and its tiered batteries, drawbridges and stairs follow the rock so closely that the fortress seems carved from it. It became a World Heritage Site in 1997 as the best preserved example of Spanish-American military architecture of its type.
From the ramparts you look across a blue bay and the green slopes of the Sierra Maestra to the west, while below the cliffs the swell surges into rocky inlets. Sunset is the time to be there, when a ceremony with costumed soldiers fires a cannon and the light goes amber over the water.
Santiago itself is the most Caribbean of Cuban cities: hot, hilly and musical, the home of son, with the Casa de la Trova in the centre where bands play from the afternoon on. It was here in 1953 that Fidel Castro led the attack on the Moncada barracks, and the city takes its revolutionary history seriously. Its carnival in July is one of the loudest in the Caribbean. Twelve kilometres west, the basilica of El Cobre houses the Virgin of Charity, patron saint of Cuba, and sits beside an old copper mine.
Riding in eastern Cuba is a real adventure. The coastal road west from Santiago towards Chivirico and Pilón runs between mountains and sea and is one of the most spectacular in the country, but storms have repeatedly damaged it, so expect potholes, washed-out sections and gravel. Traffic is light but includes horse carts, trucks with people in the back and dogs asleep on the asphalt. The heat is serious all year, and from June to November hurricane season adds a layer of uncertainty.
Fuel shortages are a recurring problem in Cuba, and stations may run dry or limit purchases, so fill whenever you can in Santiago and carry a reserve. The city has workshops of great ingenuity, used to keeping very old vehicles alive.