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. 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 Guantanamo province, passing the arid scrub and cacti of the desolate coastal strip around "that" bay and its pockets of US-controlled land. Then the rolling sierra took off and morphed into dense forest. At the first high point I looked back to see a distant blur of red-tiled roofs of the American facility, a chilling sight in view of its 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 in combat gear 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 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.
In indigenous Taíno, Baracoa means "beside the sea", but the town also wallows in a lush hinterland of coconuts, cacao, bananas and coffee. You see this best on the road east to the canyon of Yumuri which passes bucolic farmland edged by deserted beaches. Together with the trade winds, rain brings endlessly inspiring skyscapes which 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: "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 dring-dring of bicycle and pedi-cab bells, the throb of antiquated motorbikes with sidecars and the splutter and belch of American cars from the 1950s. 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, Soviet-style blocks overlook a devastated stretch slowly recovering from a hurricane in 2008.
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. After a few days I felt as if I knew everyone. There was Ramón, the dynamic postman, with his sideline of a second-hand book exchange; the peripatetic cigar-seller (whose price for the local Guantanamo smoke plunged as the nights went by); and the willowy Afro-Cuban with a heavily bandaged arm who seemed to crop up at every nocturnal venue.
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. 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 wooden lodge on the curve of a blissful white sand cove, where humming-birds, coconut palms, 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 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 moonless night: no sign of life.
Suddenly, in a whiff of rum, an apologetic Pablo appeared. Action followed: lights, crackling music, chilled beers, a family of pigs snuffling around, a strutting cockerel and, perched languidly on a stool, a young girl in a bikini. My beaming host finally materialised bearing plates of perfectly grilled dorado, rice, fried plantain and salad.
Afterwards, I wandered on to the beach to look upwards at a dense scattering of stars glinting above the palms, the same constellations that guided Columbus then Velázquez to these shores 500 years ago. For them it was the start of an adventure. For me it was the end of one: a typically haphazard Cuban finale full of warmth and theatricality, and hard to forget.
o 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.
o Another way to reach Baracoa is on Cubana from Gatwick to Holguin. Baracoa is about six hours' drive from the airport.
o It is obligatory to have travel insurance when you arrive in Cuba. Note that travel insurance policies underwritten by a US company are not valid for Cuba.
o Cuba Tourist Board: 020-7240 6655; travel2cuba.co.ukReuse content