Stepping off the beaten track in Cuba one quickly enters another world, full of discovery and exploration with pristine countryside, historic sites, graceful coastal towns and beaches and, of course, always cared for by the playful resourcefulness and creativity of the Cuban people no matter where one goes.

Still devoid of advertising, apart from scatterings of distinctive hand painted revolutionary posters, Cuba’s country roads are easy to navigate, used as much by horse and cart as by the combustion engine. Wildlife is abundant and Cuba’s elegant small towns offer outstanding hospitality, entertainment and remarkably well maintained historic sites.

Santa Clara is revolution central, being the site of a key battle in the revolutionary war of 1958. The main attraction is the Plaza de la Revolucion, where monuments are inscribed with Che’s rousing rhetoric. Also in the square is a small, moving museum dedicated to Che Guevara’s life and works, and below it, an eternal flame burns in remembrance of Che Guevara and 16 of the fighters from his failed 1967 Bolivian campaign. Another significant monument, El Monumento a la Toma del Tren Blindado, marks where the rebels derailed a train full of government troops.

Parque Vidal is a focus for gatherings of young and old alike and nearby the Museo de Artes Decorativas is filled with exquisite colonial relics: chinoiserie screens, ornate furniture, escritoires and English china, all speaking of a jewel-encrusted, distant past.

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Trinidad is the most handsome town in Cuba, its multi coloured pastel hued terraces, rust-red roofs and bell towers set against a fertile backdrop of mountain and sea. In the colonial era, especially between 1750 and 1850, sugar cane brought fabulous riches to Spanish families who built themselves gorgeous mansions around Trinidad’s main square. Now their descendants rent out rooms and provide hospitality to visitors from around the world.

Mountain and sea collide around the Topes de Collantes, producing rich soil for bountiful crops, so the home-cooked food in this area has always been superior, even in difficult economic times making it well worth enjoying the meals offered by your hosts in casa particular accommodation.

It is a short drive from Trinidad to Playa Ancon, one of the loveliest beaches in Cuba. If you can cope with all-inclusive hotels it is possible to stay by the beach, although day trips from town are, in our opinion, a better alternative.

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Cienfuegos on Cuba’s south coast, settled in 1819, is a pleasant colonial gem with pockets that look distinctly like 1950s Floridian suburbia. It is situated on a splendid bay where dolphins frolic (we can arrange for you to swim with them, if you like) and its private restaurants, or paladares, are renowned for their seafood. Other attractions include the magical Botanical Gardens created by Edwin Atkins in the early 1900s and featuring more than 2,000 species of tropical plants, and the beautiful Catedral de la Puraisima Concepcion.

Cienfuegos’s marina is the embarkation point for many catamaran excursions to the southern keys near Cayo Largo. On the Paseo del Prado, the longest street in Cuba, people watching and ice cream consumption seem to be the main event.

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Sierra Maestra is the tallest mountain range in Cuba, and has a rich revolutionary past: this is where Fidel and his band of brothers, including Che Guevara, hid after they sneaked back from Mexico to plot the 1959 Revolution. Here they hid in virgin jungle, guarded by Socialist-leaning villagers (for the cinematic version, rent Stephen Soderburgh’s Che Part I).

Until now, the Sierra Maestra has been the reserve of lone climbers, history aficionados and adventure hiking groups, but our tailor-made options allow for a private journey of discovery. At the foot of the Sierra Maestra, unspoiled Bayamo, the provincial capital of Granma, is an intriguing, rather romantic town, one of those places you can truly imbibe the ‘yesteryear’ quality of Cuba’s country lifestyle. If your luck is in you might catch an orchestra playing, or find children riding around in painted carts heaved by plump little goats.

A trek into the mountains can take you to Castro HQ, a collection of thatched shacks, including a medical centre, an assembly room, the radio room and Fidel’s austere home-from-home as well as a small museum.

Intrepid hikers can take a guide to follow a trail over a number of days, staying in a series of scattered mountain B&Bs, even ascending to Cuba’s highest peak, Pico Turquino (2000m). to peer magisterially down at the mountains below. It takes two to three days to scale, and requires a can-do attitude to camping and acceptance of the basic refuges on offer. A hike like this passes through remote coffee-cultivating villages before reaching the apex of the mountains and dropping down to the cornflower blue coast beyond. This is Fidel Castro’s journey in reverse.

Santiago de Cuba. Physically closer to Kingston Jamaica than to Havana, Santiago de Cuba is the stronghold of Afro-Cuban culture in Cuba and has a fearsome musical, cultural and political heritage. Overpoweringly hot and humid, Santiago is Cuba’s second city and features a handful of key monuments and nightspots.

The Casa de la Trova is where the city’s legendary rumba can be heard. Try not to let the surfeit of hustlers get you down: the economics of the east are even more woeful than in the west of Cuba. Santiago is Socialist to the core, a key stronghold during the nascent stages of the Revolution. The Moncada Barracks, where Fidel led a failed coup in 1953, are worth a visit, as is the Castillo del Morro, the old fortress, a romantic place to watch the sunset with panoramic views.

On the cultural side, don’t miss Santiago’s wealth of smaller museums, such as Museo Emilio Bacardi Moreau, the home of the cultural treasures of the Floridian Anejo rum king who collected everything from Egyptian mummies to creepy artefacts of slavery. In August Santiago explodes in a long, colourful, albeit sticky, summer carnival.

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Viñales Valley. To the west of Havana, the rolling green hills of Pinar de Rio unfurl Cuba’s tobacco-growing country with its old fashioned agrarian economy. Farmers trot down dusty tracks in spurs, plough the rust-red earth with oxen and sow seeds by hand. The valley of Viñales, spiked with karst limestone peaks, is a hypnotically beautiful Eden and its eponymously named little town is one of the best weekend excursions from Havana.

A functioning private-sector tourist economy means that old- fashioned country Cuban life has been spruced up for international consumption with recently painted porches, cheerful people and a host of small holding animals to explore.

Biking, caving and horse riding in the valley are the main activities for days bookended by a delicious home cooked meals. The nearest beach centre is little Cayo Levisa to the north. Cabanas pepper the 3km white sand beach and the waters are lusciously aquamarine. Snorkelling, diving, or simply reclining on a beach lounger with Hemingway and a mojito are the attraction of this coastline.

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Camaguey is a labyrinthine trail of blind alleys and forked streets, built this way to deliberately fox the rampaging pirates who dogged the town from the 16th century onwards. It is proudly well kept and rustically pretty, with a clutch of decorative facades, elaborate churches and romantic squares. Although it’s actually the third largest city in Cuba, it feels like a village. This is not a town that responds to tourists’ desires; instead maintaining its focus on a thriving family centric life of street parties, park excursions and communal restaurant meals.

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Baracoa is in Guantanamo province, the most hillbilly of Cuban provinces, a land of peasants and farms at the ends of the earth (the incongruous presence of Gitmo Bay notwithstanding). Baracoa itself sits on the deserted eastern coast looking out towards Haiti and only got its first road in the 1960s. It is a sleepy, otherworldly town, where the Taino genes are etched on the faces of locals and where indigenous cooking methods such as cooking on palm leaves with cacao and coconut are mainstream. None the less, Baracoa’s has a long history. In 1492 it was Columbus’s second landfall in the New World and Cuba’s capital from 1518 to 1522. Visit the Taino museum, housed in a cave and an old Taino burial site.

Baracoa sits amid the most enchanted and remote landscape in Cuba – palm covered, wild, with clear rivers and peaceful rugged beaches under a vast and sometimes volatile sky.

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Holguin is the capital of the province to which it gives its name. Ringed by mountains, it is a pleasantly civilised city of gardens, plazas and parks, although lacks the colonial grandeur and romance of Camaguey or Trinidad.

The province at large is home to some of the most beautiful beaches, mountains and isolated rural communities in Cuba, including the idyllic property where Raul and Fidel Castro grew up. The sleepy town of Gibara features whitewashed houses topped with red roofs, is an undiscovered gem with the largest number of artists per capita in Cub. Gibara explodes with activity during the Low Budget International Film Festival (Festival Internacional de Cine Pobre), which has been going for more than a decade and features concerts, theatre and exhibitions as well as the cinematic programme.

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