At strategic spots along the near-deserted road, locals dangled bunches of tiny bananas, strings of mandarins, cucuruchos (cones of pineapple and coconut paste), recycled bottles of wild honey, solid lumps of cacao and bags of coffee beans. Pulling in, I ended up having a chat, added a few pesos to their income and learnt how desirable a bar of soap was. This basic yet rare commodity costs a fortune: a whispered "Jabón, jabón" became a leitmotif of the trip.
I was driving over La Farola, Cuba's highest mountain road and an engineering feat of the brave new Cuba of the early 1960s. Although the road was nothing like as bad as I had been warned, it took nearly five hours to drive the 230km from my starting point, Santiago, to my destination on the north coast – Baracoa. The route curled through the unlikely tourist destination of Guantánamo province, passing the arid scrub and cacti of the desolate coastal strip around "that" bay and its anachronistic pockets of US-controlled land.
Then the rolling sierra took off and morphed into dense forest for mile after spectacular mile. At the first high point, I looked back to see the distant blur of red-tiled roofs of the American facility, a chilling sight in view of its remaining 171 detainees. Far down the slopes was an occasional wooden shack, but the otherwise limitless, undulating green was a reminder of how vital Baracoa's sea access had been before La Farola was built.
Monday marks the 500th anniversary of this first Spanish settlement on Cuban soil, which was a curtain-raiser to the virtual extinction of the island's Taíno inhabitants and the genesis of an Afro-Hispanic culture unlike any other. Centuries later, in 1959, the Cuban Revolution added another dimension. Giant cut-out figures of Che are likely to greet you from hilltops; affectionate references to "Fidel y Raul" decorate shop walls; endless political slogans dot the roadside. Back in 1515, the conquistador Diego Velázquez transferred the Cuban capital to Santiago, and Baracoa became a backwater.
Pirate attacks nonetheless demanded that the town retain muscular forts, which now respectively house a dusty municipal museum, a restaurant and a hilltop government-run hotel called El Castillo. With unbeatable views over the bay and the Atlantic, it's definitely the best place to stay.
In indigenous Taíno, Baracoa means "beside the sea", but the town also wallows in a lush hinterland of coconuts, cacao, bananas and coffee, nurtured by the highest rainfall in Cuba. You see this best on the road east to the dramatic canyon of Yumurí, which, after crossing the Río de Miel ("honey river"), passes bucolic farmland edged by deserted beaches. Together with the north-eastern trade winds, rain brings endlessly inspiring skyscapes, which, whatever their mood, frame the iconic silhouette of El Yunque – "The Anvil".
This limestone outcrop allegedly inspired Columbus's 1492 diary entry describing "a high and square mountain that looks like an island..." He continued lyrically: "I have never seen a more beautiful place. Along the banks of the river were trees... flowers and fruit of the most diverse kinds, among the branches of which one heard the delightful chirping of birds."
Today, you could add to those warbles the clip-clop of pony-cart taxis, the rattle of bullock-carts, the ring-ring of bicycle and pedi-cab bells, the throb of antiquated motorbikes with sidecars, and the splutter and belch of American cars from the 1950s (nearly all resprayed in a lurid mint green or fearless turquoise). And at night there's the inevitable blast of live son and changüí – the local cubano music.
Architecturally, it's a bizarre juxtaposition of vividly painted clapboard beside ornately stuccoed and colonnaded beauties from Baracoa's big 1930s comeback, when bananas became the "green gold" that reaped fortunes. On the seafront, incongruous Soviet-style blocks overlook a devastated stretch slowly recovering from a hurricane in 2008, but the action all happens a block or so inland.
Every street tells a story of past glories. At the excellent paladar (privately run restaurant) El Colonial, chandeliers illuminate sweet, fresh lobster in a divine coconut sauce. Yet, despite this decorative nostalgia and Cuba's economic woes, the town seems to thrive on an energetic individualism, peaking at night. Brilliant musicians– legions of them – play at the funky Casa de la Trova beside the gutted cathedral, which is undergoing a painful renovation.
More local still, the beaten-up El Patio heaves with dancers and drinkers. One evening, a veteran guitarist in an immaculate white guayabera even lured me into the Casa de la Cultura to lend a hand on percussion in his otherwise masterful son band.
After a few days, I felt as if I knew everyone, and they certainly knew me. There was Ramón, the dynamic postman, with his sideline of a second-hand book exchange; the peripatetic cigar-seller (whose price for the local Guantánamo smoke plunged dramatically as the nights went by); and the willowy Afro-Cuban with a heavily bandaged arm who seemed to crop up at every nocturnal venue, talking wildly.
More measured in style was René Frometa, an 82-year-old painter. He turned out to be guardian of the legacy of his adoptive mother, a Russian aristocrat ("La Rusa", now the name of the hotel she opened in 1953, where she later hosted and supported the revolutionaries Fidel, Raul and Che).
Dragging myself away from the charms of this time-locked, end-of-the-world place, I headed west to Playa Maguana in search of a swim. This lay a 25km crawl along a spectacularly cratered road that crossed several rivers, including the broad, crystalline Río Toa. En route, hitchhikers piled in to my hire car – a very Cuban form of public transport. In the background the hills were clad in a tangle of vegetation.
The area is now a national park named after the great Prussian naturalist, Alexander von Humboldt. Egrets and hawks winged past while children splashed in the shallows.
The idyll continued at Villa Maguana, a small-scale wooden lodge on the curve of a blissful white sand cove, where hummingbirds, coconut palms, giant scarlet hibiscus, a coral reef washed in a palette of blues and the lull of gently rolling surf all compounded the Caribbean magic.
Nothing is perfect though, and the sleepiness of the hotel service soon forced me to venture out in search of better food and sharper attention. On the neighbouring beach, I discovered a laid-back chiringuito (beach bar), where I arranged dinner with the owner, Pablo. Later that evening, the headlights of my car picked out the thatched bar in the pitch black, moonless night: no sign of life. Cuban indifference? Unlikely, given the lure of the convertible peso, the curious home-grown hard currency.
Suddenly, out of the night, appeared an apologetic Pablo, in a whiff of rum. Action followed: lights, crackling music, chilled beers, a family of pigs snuffling round the edge of the deck, a strutting cockerel and, perched languidly on a stool in the corner, a young girl still in a bikini despite the night chill. The surreal performance continued as a dreadlocked groover appeared from nowhere to dance salsa with her, then an older Cuban leading a goat on a string shuffled in for a beer. My beaming host finally materialised bearing plates of perfectly grilled dorado, rice, fried plantain and a salad of home-grown tomatoes.
Afterwards, digesting the food and ambiance with the usual añejo rum, I wandered on to the shadowy beach to look upwards at a dense scattering of stars glinting above the palms, the same constellations that guided Columbus and then Diego Velázquez to these shores 500 years ago.
For them, it was the beginning of an adventure. For me, it was the end: a typically haphazard Cuban finale full of warmth and theatricality, and hard to forget.
Travel essentials: Baracoa
* The writer travelled with Travelzest's Captivating Cuba (0800 171 2150; captivatingcuba.com), which arranges tailor-made holidays to Cuba, including car rental and flights from Gatwick to Havana with Virgin Atlantic. There are frequent domestic flights from Havana to Santiago, and occasional departures to Baracoa's tiny airport.
* An alternative from the UK is on Cubana from Gatwick to Holguín, which Travelzest's Captivating Cuba can also arrange. Baracoa is about six hours' drive from the airport, depending on road conditions.
* Tropical rain is frequent in Baracoa, but the months of November to March see less, as well as maximum temperatures in the low 30s.
* It is obligatory to have travel insurance – and to carry the policy – when you arrive in Cuba. Note that travel insurance policies underwritten by an American company, such as those issued by Boots, are not valid for Cuba.
* American dollar travellers' cheques and US credit cards are not accepted in Cuba. On arrival, sterling can be changed easily into convertible pesos (CUCs), the foreigners' currency, much sought after by Cubans.
* Cuba Tourist Board: 020-7240 6655; travel2cuba.co.uk