Take the wheel: hire a car in Havana to explore the rest of the island / Getty

Take to the open road to explore the biggest of the islands in the Caribbean close-up

The Caribbean's largest island – the size of England – is ideal for a fly-drive adventure. Cuba is the only nation that invites you to drive through superb tropical landscapes, on lightly travelled roads, in the company of vehicles that are relics from half-a-century ago. You can drive where you please, alternating between glorious colonial towns and dazzling beaches as you cover the ground between the scenic tobacco-growing lands of western Cuba and the wild countryside and revolutionary history of the east.

Rental cars are readily available and good value, typically around £40 per day, fully inclusive. You need not rent a car for the full duration of your stay; in Havana, a vehicle will be a disadvantage. You might alternatively be staying in one of the big resorts, such as Varadero and Guardalavaca, and want to opt out for a few days. Cuba lends itself to impromptu decisions because accommodation is so plentiful: besides some excellent hotels, highlighted here, you can find plenty of casas particulares – private homes– offering comfortable rooms for as little as 25 convertible pesos (written CUC25, and worth £16).

Don't be too ambitious about the distances you intend to cover. After all, you need to make the most of being on the road. The excellent Guía de Carreteras de Cuba (Highway Guide of Cuba) is widely available on the island. It is bilingual Spanish/English and has detailed regional charts plus street maps for all the significant towns and cities. Fuel is widely available at prices that are low by UK standards. Hitch-hikers are seen everywhere. While you need not feel any obligation to pick people up, most visitors who do find it an excellent way to meet the locals.

If you take the only non-stop scheduled flights to Havana, on Virgin Atlantic (0344 209 7777; virgin-atlantic.com) from Gatwick, my advice is to start by driving away from the capital. A good first move is to go west on the Autopista Nacional – the backbone of the road network.

In Pinar del Rio province, the Cordillera de Guaniguanico provides a stirring upland companion. The range includes the Sierra de los Organos with the bizarre mogotes – large limestone humps which rise dramatically out of the tobacco fields of the Viñales valley.

Viñales offers splendid hiking as well as the most environmentally sensitive aspects of tourism in Cuba. A great place to stay is the Hotel Los Jazmines, a handsome early 20th-century mansion with superb views. Then explore the Viñales National Park north of the town, with fascinating caves and spectacular views. Next, move gently east, possibly pausing at the southern port of Batabanó for a side-trip to Isla de la Juventud ("Isle of Youth") – for some rejuvenation and diving. Ferries are erratic, though, and you may want to leave your car on the mainland.

The Zapata Peninsula gets its name from the shape on the map – like a shoe (zapata) kicking into the Gulf of Batabanó – and it is Cuba's prime rainforest area. Continuing west, you can tick off one fascinating city after another: Cienfuegos, Trinidad, Sanctí Spíritus and Ciego de Avila. By now the autopista has ended, and the journey continues on the Carretera Central. Camagüey is certainly worth a stop. And make a detour to Bayamo and the province of Granma. (Granma, by the way, means "grandmother" – the name of the cabin cruiser used by Che Guevara, Fidel Castro and their comrades, for the 1956 landing that began the revolution.)

The beaches along the flat south-eastern shore are superb, but the towns and cities are even more compelling. Santiago, "Hero City of the Revolution", contains the Moncada Barracks, where Castro led his first attempt to overthrow the Batista regime. Drive into the Sierra Maestra, where the rebels set up camp while rousing support to continue the struggle.

Further west, Baracoa, close to Cuba's "Land's End", is reached by a sinuous drive through the mountains. It is a sleepy, seductive town that captivated Columbus in 1492. Feeling adventurous? The north-coast road can be challenging, but is usually passable with a bit of care. The resort of Guardalavaca provides en-route indulgence, while Holguín is a friendly city where you can get under the skin of Cuba.

View Simon Calder's fly-drive adventures on the island at independent.co.uk/autenticacuba

Escape the capital

The Capitolio building in Havana is an excellent place to survey automotive history – with one spluttering old relic from Detroit after another – before heading south-east.

Get in touch with the nature of the island at Guamá, where you can board a boat to explore more deeply. You are taken across the Laguna del Tesoro ("Treasure Lake") which was named so because, after the conquistadores arrived, the locals threw their riches into the water rather than give them up.

A Taíno village has been recreated, with thatched huts on stilts dotted around the island.

Close by, the Cueva de los Peces is the deepest flooded tectonic fault in Cuba – and a great place to cool off. It translates as "the cave of the fish", and is said to be more than 200ft deep.

Playa Girón is central to the story of 20th-century Cuba: it was the location for the failed the Bay of Pigs invasion of 1962, and is now home to an all-inclusive resort and some idyllic scenery.

Class and coffee

A newly opened road cuts a big corner across the south of Cuba and gives faster access to Cienfuegos (left). By the standards of Cuban cities, Cienfuegos is relatively new – established in 1819 – and rather lovely. Founded by a French settler, Louis Clement, it is full of 19th-century French architecture. The Hotel La Unión (00 53 43 551020; hotellaunion-cuba.com) is right in the centre. Good double rooms cost CUC64 (£40), room only.

A block away, the main square, the Parque José Martí, is home to the exquisite Teatro Tomas Terry and the governor's palace. And there's the even more impressive Palacio de Valle, perched by the water at Punta Gorda – a lavish Hispanic-Moorish masterpiece.

From Cienfuegos, you can follow the coast east and climb into the Escambray Mountains, which rise majestically north of the shore. Topes de Collantes is a high-altitude hill resort at the heart of Cuba's coffee country – claimed to rank with the Blue Mountains of Jamaica as producing the best arabica beans in the world.

Live the high life

Trinidad, the jewel of Cuban tradition, has been on the Unesco world heritage list since 1988. Established by the Spanish in 1514, the city is full of beautiful mansions, and the highest density of bars and restaurants in the country.

Try the 17th-century tavern known as La Canchánchara, and visit the Casa de la Trova (House of the Troubadours) the social and musical hub of the city. Splash out at the five- star Iberostar Grand (00 53 41 996 070; bit.ly/GrandTrinidad), where a double room (no breakfast) typically costs €174.

Just north of Trinidad, explore the Valle de los Ingenios. Dozens of sugar mills once dotted this landscape and, today, a few relics of the era still survive.

The Torre Manaca Iznaga is 144 feet and 244 steps high. At the start of the 19th century, a rebellion by slaves in neighbouring Haiti caused the sugar barons to flee to Cuba where they built watchtowers such as this one to keep an eye out for possible insurrection.


Cuba's heartland

Sanctí Spíritus is the unspoiled, good-looking and relaxed face of Cuba. La Iglesia Parroquia Mejor del Sanctí Spíritus ("The Church of the Holy Spirit") is claimed to be the oldest surviving place of worship in Cuba. Sanctí Spíritus is also a good place to sample Cuban specialities such as fresh coconuts and churros (deep-fried dough).

Remedios is a sleepy town in Cuba's Midwest that will delight your inner photographer. The main sight in Remedios is the church of San Juan, where there are three photogenic points: the first is the elaborate altar, then there's the figure of the Virgin of the Good Journey, who some say should be Cuba's patron saint, and, finally, there's the only sculpture in Latin America of the Immaculate Conception where Mary is depicted as already pregnant.

If you do like to be beside the seaside, drive out across the Atlantic along el Pedraplen – an impressive causeway that extends out from the shore near Remedios to connect a string of small islands and provide a platform for a new playground for holidaymakers.

The first development was on Cayo las Brujas – meaning "Isle of The Witches". With an ocean breeze and the tropical sun setting in the west at the end of a glorious day, together with the prospect of being lulled to sleep by the Atlantic's waves, it is the perfect place to break a journey.

Local hero

Santa Clara would be a pleasant but unremarkable city in central Cuba were it not for one event that marked the climax of the revolutionary struggle.

By late December 1958, Fidel Castro and his fellow rebels had fought their way from the south-east of the island to the centre. Che Guevara led the rebels to victory in the decisive Battle of Santa Clara, and was revered for his part in the triumph of the revolution.

Guevara became the minister of banking and industry for the new government in Havana. But he had always vowed to fight injustice in Latin America and by 1967 was in Bolivia seeking to spark revolution there.

He never returned to Cuba; he was captured and, on 8 October 1967, was shot dead. Three decades later, his remains were brought to Santa Clara to be interred alongside his comrades at the Plaza de la Revolución – a sombre place to contemplate Che's enduring influence on Cuba and the world.

The northern circuit

A good plan is to take the autopista away from Havana, but the Circuito Norte back to the capital. It meanders through the countryside and sleepy towns such as Cárdenas.

Around the start of the 20th century, wealthy citizens from Cárdenas built themselves summer houses on a narrow peninsula jutting into the Atlantic to the north. Today, Varadero is Cuba's leading beach destination – a 12-mile sliver of dunes lined with hotels and all-inclusive resorts – plus a Beatles Bar on the main drag (live music from 10pm to 1am, eight days a week). A marina has just been opened at the end of the peninsula.

To the west, the Cuevas de Bellamar claims to be Cuba's oldest tourist spot, dating back to 1861. The caves extend for more than two miles, reaching a depth of 105ft and include extraordinary natural sculptures.

The most spectacular stretch of the Via Blanca is the Bridge of Bacunayaguey – the longest and highest in Cuba. The span is more than 1,000ft, and it's 300ft above the valley. It was officially opened by Fidel Castro shortly after he came to power in 1959.

The fishing village of Cojímar makes a final detour for an encounter with one of the 20th century's great writers. Ernest Hemingway was seduced by Cuba in the 1930s and it was here that he was inspired to write The Old Man and the Sea, which won the Nobel Prize for Literature.