Like so many famous places in Cuba, Santiago feels small, with a handful of key venues. The place to hear the city's cutting-edge salsa and rumba is La Casa de la Trova, where the tables and balconies are packed with tourists and lady hustlers. From the top of the Casa Grande hotel you can see the whole city, starting with the bell towers of the beautiful Nuestra Señora de la Asunción. For epic scale, there's the Castillo del Morro, the old fortress outside town, at dusk.

If you seek revolutionary history, Santiago has it in spades: Santiago people were always more Cuban, less Spanish, and prone to disobedience. The Moncada Barracks, where Fidel led a failed coup in 1953, are here but we don't visit. I'm interested in what the Cuban government calls "the triumph of the revolution" but I'm tired of being force-fed it.

More decadent is the Museo Emilio Bacardí Moreau, which houses the art and archeological collection of the former Santiago mayor and rum king. It has everything from Egyptian mummies to sinister slave-whipping devices. I wonder when the Bacardí family will return to try and claim it back.

Our last stop is the most eastern of the eastern towns: Baracoa. The road from Santiago to here passes through the wild-west-style country town of Guantánamo and skips over the top of Guantánamo Bay before hugging a deserted coastline. From our Chinese-made bus we pass resting farm workers in high, straw-thatched hats sitting in carts next to their oxen. They look like people you might squint at in a scuffed black-and-white photograph. It is hard to imagine Gitmo just "over there" on the other side of the cactus curtain, with its mini movie theatres and McDonald's.

Then the bus scales La Farola, the road that was cut through the Sierra del Purial in the 1960s and opened Baracoa to the world. The bends are speckled with clapboard dwellings with cottage gardens, where women sell mandarins, Baracoan chocolate and cucurucho – a cloying mixture of coconut, orange, guava and sugar sold in cones made of palm leaves.

Cuba was Columbus's second landfall in the New World, and Baracoa was his first port of call, in 1492. He planted a cross in the ground and got an enthusiastic greeting from the doomed Taíno Indians. Diego Velázquez founded the first colonial town in the Americas here in 1512, and it was Cuba's capital from 1518 to 1522.

You wouldn't know it. This is not a town trumpeting faded colonial grandeur; rather it is a village in disrepair, with colonnaded colonial shacks in tumbledown rows, where cockerels, piglets and strays mingle with children. The cathedral is a shell awaiting restoration, and Columbus's Cruz de la Parra has been removed to a house on a side street. The northern part of town is full of the scent of cocoa: Baracoa has Cuba's only chocolate factory.

Cut off by the mountains for centuries, Baracoa remained sequestered, the only place you could still see the genes of Taíno Indians in the faces of the locals. It was here that the 16th-century Taíno chief Hatuey raised an army to fight the Spanish. Away from the centre, the town drifts upwards into the hills, its houses dotted among palms, breadfruit and mango trees. The archaeological museum is housed in caves that are Taíno burial sites: skeletons rest in the foetal position alongside a trove of pre-Columbian artefacts. It's surrounded by shacks among banana trees; to reach it you push through washing strung between fat palms, and paths criss-crossed by piglets. We are the only people there.

We stay in hotel El Castillo, one of Baracoa's old fortifications. From its pool you can see the town's greatest asset: the whole, glistening countryside, from the mist-covered flat peak of El Yunque to the snaking rivers and brooding seas. There is no doubt that this is the most enchanted landscape in the whole of Cuba.

Much of the time we are in Baracoa it thunders and pours, so we sit in rocking chairs on the dripping porch and watch the landscape turn against itself. The skies light up, water gushes down from the hills, the rivers turn a strange burgundy and the sea goes an apocalyptic brown. When the rains abate we visit the mouth of the Rio Toa. Under storm-cloud skies we find a wilderness beach with a thousand tides' worth of coconut husks and driftwood scattered over it, huddled beneath towering royal palms.

The Toa, a dark emerald green, swirls moodily into the sea. We see three people fishing quietly, a clutch of girls washing clothes and two lovers embracing in the shallows. We hike up to El Yunque, the remnant of a plateau so isolated it has its own species of ferns and palms. At the mouth of the Rio Yumuri, which cuts through stunning gorges, we eat coconut-poached snapper prepared by women in tumbledown houses on the beach.

We end at Playa Maguana, a beach 25km north of Baracoa where we stay at Villa Maguana, an elegant beach shack, with 12 spacious timber-built rooms. A villager called Javier brings us home-cooked lobster, plantain and salad on the beach for a princely £2.60, and slices off the tops of green coconuts for us to drink. We eat the lobster, observed by a giant, malodorous pig, and ponder how to get out of here.

Rain is expected again, and tomorrow we need to find someone to take us the 25 muddy kilometres to Baracoa, so we can catch a bus to Santiago, as all the planes are booked. It's an odyssey, but then that feels right for a place that looks like the Garden of Eden at the end of the earth.

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Journey to Birán in search of Castro's past
Jun / 2010