See the best of Cuba with these two classic itineraries

The more you try to understand Cuba, the more mysterious it becomes. Welcome to a nation of envelope-pushing art and head-scratching bureaucracy, where doctors moonlight as taxi drivers, Argentine revolutionary Che Guevara is a national hero and 1950s US cars run on 1980s Soviet engines.

Some days, the contradictions drive you mad; others, they bring you out in a shiver of excited goosebumps. Where else is such a talented and resilient populace able to create so much out of so little? It’s a country that contrasts Afro-Spanish dances with mildewed baroque and classical architecture, where the private lives of ordinary people are played out in the streets. The dichotomies that travellers will bear witness to are a large part of what makes Cuba such a compelling destination — a legacy of its time as a Spanish colony made up of European settlers, Indigenous people and enslaved Africans. The cultural mix diversified even more in the 20th century, during successive periods of US and Soviet influence.

Even by its own austere standards, the country’s recent economic situation has been challenging. The tightening of the US embargo, mixed with crumbling infrastructure and the downward spiral of well-established allies in Venezuela, has resulted in food queues, fuel shortages and crippling power cuts on an almost daily basis.

But don’t let the superficial scruffiness put you off. In Cuba, unheralded marvels hide beneath an opaque veneer. Maestro musicians light up unkempt bars and priceless paintings are displayed in shabby museums. Tourism has been down since the pandemic, but those who visit and venture beyond the country’s coast-hugging, all-inclusive resorts can expect a bounty of unscripted adventures.

Rather like its neighbours in the Cayman Islands and Bahamas, Cuba’s beaches are abundant and beautiful. The 12-mile-long strip of diamond-dust sand at Playa Varadero is known for its big resorts, but there are many quieter stretches to discover, too. Syncopated music genres such as Son Cubano — once described by ethnologist Fernando Ortiz as a love affair between the Spanish guitar and the African drum — continue to emanate out of every club, restaurant and backstreet bar. The people — indomitable, gritty and inexhaustibly creative — retain their characteristic energy and wit.

Less obvious attractions include some spectacular birdwatching and zesty criollo food (Spanish-influenced home-cooking starring rice and beans), which, thanks to the industriousness of innovative local chefs, has rediscovered its roots. The island is also home to several fast-growing niche sports, including kiteboarding, which takes advantage of the stiff winds that caress the northern keys. While the government struggles to keep the lights on and patient motorists form long lines outside petrol stations, the bright glow of the country’s artistic and cultural talent shows no signs of abating — and unlike some destinations around the world, it’s eager to welcome more travellers. Pack a head-torch, draw up a flexible itinerary and launch into Cuba’s irresistible maelstrom.

Itinerary 1: Best of the West

Start point: Havana
End point: Guanahacabibes
Distance travelled: 300 miles
Average length: 7 days

Kick off your trip by enjoying a day or two in the urban melee of Havana before heading west to become enmeshed in a bucolic world of misty tobacco plantations and precipitous haystack-shaped hills called mogotes. Western Cuba is the spiritual home of cigar-puffing Cuban farmers known as guajiros, who ride around on horseback and still use oxen to plough their fields. The terrain in these parts — a patchwork of rust-red pastures dotted with royal palms and simple thatched homesteads — is considered the best place in the world for growing tobacco. You can organise activities — such as horse-riding, hiking and farm visits — in several villages that punctuate the hilly landscape. The most notable of these is Viñales, a small farming community that anchors an eponymous national park and UNESCO World Heritage Site.

Further west, you’ll need your own vehicle as the settlements thin out and the roads become increasingly bumpy. This route offers a great insight into rural Cuban life, with locals getting around by horse and cart or hitchhiking. The country ends at a thin boot-shaped peninsula, home to the ecologically diverse Parque Nacional Península de Guanahacabibes — remote, but well worth the journey.

1. Havana
On the northwest coast, the national capital is the epicentre of Cuban culture and the best place in the country to sample food, art, architecture and music. Investigate all four at the Fábrica de Arte Cubano, an art ‘factory’ and performance space where it’s possible to catch chamber music and avant-garde rap on the same evening. Stay at Casa 1932 from US$40 (£30) per night, B&B; the hotel is located a block from the seafront Malecón strip in Centro Havana and furnished with art deco decor.

2. Las Terrazas
Hire a car and driver and head around 50 miles west of Havana, swapping salsa for sustainability at Las Terrazas. This whitewashed eco-village clings to the forested hillsides of the Sierra del Rosario. Designated Cuba’s first UNESCO Biosphere Reserve in 1984, the community is the result of a successful reforestation project dating from the 1960s. It now functions as a tourist complex offering guided hiking, homegrown coffee and Cuba’s longest zip-line.

3. Soroa
A 12-mile drive west of Las Terrazas, the pinprick community of Soroa is known as the ‘rainbow of Cuba’, courtesy of its colourful natural foliage, refreshing waterfalls and abundance of equally vivid orchids. You can enjoy the floral extravaganza at the terraced Orquideario, a botanical garden housing more than 800 species.

4. Viñales
Western Cuba’s rural hub sits amid the steep craggy hills of Pinar del Rio province in the centre of Cuba’s tobacco-growing region. A strong culture of agrotourism has developed here. In between hiking, horse-riding and zip-lining, you can visit the Finca Agroecológica El Olivo, a sustainable farm, and follow the Ruta de Queso (cheese trail), learning about how the farmers grow crops and produce goat’s cheese for their restaurant in Viñales. Tastings are included.

5. Cayo Jutías
Cuba’s northwest coast isn’t over-endowed with beaches, which makes the powdery-white sands on this tranquil island extra precious. Unblemished by resorts or tourist clutter, it sports a beach-shack restaurant and calm translucent waters that were made for snorkelling. You’ll need your own wheels to get here, or you can join an organised day trip from Viñales, some 35 miles to the southeast.

6. Guanahacabibes
This uninhabited national park, an hour’s drive from Viñales, is famed for the rare flora and fauna that’s developed among a landscape of karst mountains, lagoons, petrified trees, palms, mangroves and offshore coral reefs. To tour it, you must have your own vehicle and enlist the services of an official guide at the park entrance near La Bajada. A lonesome 40-mile-long coastal road forges through the park to Cuba’s most westerly point passing cenotes (natural sinkholes), shipwrecks, crab colonies and wild beaches that serve as nesting sites for loggerhead turtles.

Itinerary 2: Cuba’s heartlands

Start point: Matanzas
End point: Morón
Distance travelled: 375 miles
Average length: 10 days

Many of Cuba’s defining characteristics can be found in its central region, a diverse mix of swamp, mountains, farmland and mangrove-rimmed keys that incorporates the provinces of Matanzas, Cienfuegos, Villa Clara, Sancti Spíritus and Ciego de Ávila.

While most travellers park their suitcases in Varadero, a giant beach resort on the north coast, increasing numbers have woken up to the more erudite joys of the city of Matanzas. Lying 22 miles to the west, the provincial capital is famed for its divergent musical genres and religions of African origin.

On the south coast, the UNESCO-listed city of Cienfuegos — founded by French emigrees in 1819 — is another highlight. Further east, Viazul buses connect to UNESCO-listed Trinidad, one of Cuba’s seven original towns established by Spanish conquistador Diego Velázquez three centuries ago. The Zapata Peninsula in the south is radically different: flat, lightly populated and covered by the Caribbean’s largest swamp. The region acquired infamy in 1961 for the botched invasion at the Bay of Pigs. In the years since, it’s become a tranquil haven for birdwatchers and divers. Two days here will give you a decent insight into the region.

1. Matanzas
Once dubbed the ‘Athens of Cuba’ for its artistic and literary leanings, the bay-side city of Matanzas (population: 145,000) has rekindled its cultural charm thanks to a mix of government investment and creative local talent. You can see the best of it on Calle Narváez, a riverside art street, and in the hallowed confines of the Sala White and the Teatro Sauto, two historic spaces dating from the 1860s that offer very affordable and engaging music performances.

2. Bay of Pigs
Known to the outside world as the place where the Cold War nearly got hot in the 1960s, the Bay of Pigs is hemmed in by the wildlife-rich Ciénaga de Zapata swamp and is home to Cuba’s most affordable scuba-diving. Divers can swim out to a sharp underwater drop-off that runs the length of the bay, a mere 150ft offshore. Stay in the beachside village of Playa Girón.

3. Cienfuegos
Cuba’s elegant French-influenced city is renowned for its palatial buildings — all refined neoclassical columns and ostentatious rooftop cupolas. Some of the edifices have been reborn as museums, restaurants and private homestays. The finest examples encircle salubrious Parque José Martí in the city centre.

4. Trinidad
One of the best-preserved Colonial-era towns in Latin America, Trinidad remains little changed since its sugar-producing heyday in the 1850s. Famed for its cobbled streets and grandiose mansions, it has recently sprouted some accomplished private restaurants, including Muñoz Tapas, where you can enjoy local classics like lobster, shredded beef and chunky Cuban sandwiches.

5. Santa Clara
Arguably Cuba’s edgiest city, Santa Clara makes up for its lack of grand buildings with an exciting nightlife, revolutionary history and strong attachment to Che Guevara. The Argentine fighter successfully derailed an armoured train here in 1958, which ultimately sealed the fate of the Batista regime and marked victory for Castro’s Cuban Revolution. Learn about his controversial legacy at the Che Guevara mausoleum and museum.

6. Morón
The little-visited but proudly Cuban town of Morón, a three-hour drive east of Santa Clara, is a base for some of Cuba’s best freshwater fishing and boating. The action centres on nearby Laguna La Redonda, where you can sign up for tours of the mangrove-fringed lagoon in a motorboat — with or without fishing tackle.