Find the perfect beach, listen to the best music and fall into the rhythm of this beguiling country – both on the dancefloor and in its somnolent countryside
One of the most historic cities of the Caribbean, Havana is a unique architectural, social and cultural mix. Classic cars, chunky cigars and music blasting from every window also make it one of the most atmospheric – and a true travel icon.
You’ll probably want to start in Old Havana. It’s best explored on foot, with a judicious mojito pit-stop or two. A comprehensive tour would include the old city’s beating heart – its four great colonial plazas: de la Catedral, de Armas, de San Francisco, and Vieja. Don’t miss el Capitolio, (the National Capitol Building), the Prado boulevard, and watering holes such as el Floridita (a favourite with Hemingway).
Cuban ladies on the streets of Havana (Shutterstock.com)
At sunset, head to the Malecón – the city’s sea wall – and walk from one end to the other. Here you’ll meet fishermen and lovers, musicians and clowns – all manner of Cubans doing what they’re so good at: being here.
Forget the officious state-run hotels. The best way to unravel the baffling enigmas of modern-day Cuba is to stay in a privately run bed and breakfast.
Safe, clean and gloriously retro, these authentic family homes present Cuba as the Cubans see it: a fascinatingly contradictory country where vintage Chevrolets run on Lada engines and the national doctors get paid less than tip-collecting waiters in Varadero.
Cuban balconies (Shutterstock.com)
Known locally as casas particulares, Cuban B&Bs run the gamut of majestic colonial mansions in Trinidad to simple clapboard beach houses in Baracoa. But, while no two casas are exactly alike, they all offer something that no hotel can ever replicate: a sharp and vivid snapshot of everyday Cuban life, unguarded and uncensored, with all of its fun, foibles and unfathomable secrets.
The beauty of cycling in Cuba is that once you get out of Havana, pedestrians outnumber vehicles and your biggest obstacle is dodging the dogs sleeping on the warm tarmac. Here Cuba operates on a more somnolent timetable and one that is perfectly suited to cyclists.
Cycling in Trinidad (Shutterstock.com)
You’ll amble through a flawless landscape of green – forest-clad, rolling hills swathed in thin wisps of errant cloud. Dewy creepers hang down limply from the branches, glinting in the early light, and twittering birds sit gossiping on the telephone wires as you pedal by.
Cuba is one of the world’s great musical destinations. And since the release of the Buena Vista Social Club CD, music has been a part of Cuba’s international image. Walk the streets of Havana and you’re almost guaranteed to be serenaded by a group of soneros strumming ‘Chan Chan’.
Cuban street musician (Shutterstock.com)
Thankfully, music is such an essential part of Cuban life that it doesn’t take much effort to unearth a more authentic experience. Ask around – Cubans are more than happy to share the names of their favourite clubs and bars. From Afro-Cuban rumba to son and reggaeton, you’ll soon find yourself shaking your booty like a local.
Baracoa is Cuba's oldest settlement and was one of the first landing sites for Christopher Columbus back in 1492. Tucked away in the far eastern corner of Cuba, Baracoa’s distance from Havana makes it one of the least visited areas of the country.
Travellers venturing down here are captivated by the scenic journey, snaking along mountain sides before a final descent into this quaint little city, overlooked by the imposing tabletop mountain – El Yunque.
Beach near Baracoa (Shutterstock.com)
Surrounded by lush rainforest and stunning secluded beaches, Baracoa is a world away from the hustle and bustle of Havana and well worth a visit to see another side to this fascinating country. Local people have kept their traditions and continue to preserve the region’s pristine eco-system. Cocoa trees are found in abundance in the local area so be sure to sample the local chocolate.
This delightful colonial town just an hour from Trinidad is full of charm and character and much over-looked by most visitors to Cuba. Like Trinidad, it was founded by Diego Velazquez in 1514 and became the military, political and economic centre of the area in the colonial period.
This led to the city being embellished with elegant 17th and 18th century mansions with a compact and attractive colonial centre similar to Trinidad's but far more peaceful with appealingly local authenticity. There is a simple but charming hotel located right on its attractive central plaza called the Hotel del Rijo. A stay here can make a welcome break from the humdrum of Cuba’s larger cities.
You can tour a cigar factory in Havana – both the Partagas and Romeo y Julieta factories are popular. And chances are a local will sidle up to you and offer a cut-price box of Cohibas, smuggled out of the factory by a relative or friend. But for a real adventure, head to the source, the tobacco farms around Trinidad.
Local lady smoking a cigar in Havana (Shutterstock.com)
Follow your nose to the little ramshackle coffee huts that dot the area. The owner will motion you towards a seat and grind the beans in front of you. Best of all, each cup of coffee comes with a complimentary cigar. All for a fraction of the cost of a Latte back home.
If Havana feels like time has stood still, then it has gone backwards in 'el campo', the Cuban countryside. If you stop anywhere, people will be keen to chat and show you around – you may even be invited in for a drink or something to eat. Put down your camera and guidebook, and take time to talk to the curious and friendly Cubans you will meet off the tourist trail.
Transport tails off the further you are from the cities, so you’ll probably need to rent a car to get the most ‘el campo’ and explore hamlets and little towns. The road from Pinar del Río to the far Western tip of the island is a joy, speckled with pretty villages, lush vegetation and farmsteads. Make sure you stop at the roadside stalls selling fruit. Knobbly, misshapen and full of flavour, it’s much tastier than any you’ll get at home.
Guantánamo Bay may be notorious for its US base, but it’s also a Cuban province of cultural diversity and surprising splendour. And it’s beautiful too: a sweeping horseshoe of turquoise, it’s so sheltered that it can offer a fleet protection from the fiercest of Caribbean hurricanes.
At Caimanera, the nearest Cuban town to the US naval base, locals while away weekend afternoons with cans of Bucanero beer in a beach bar, while their children swim in the bay’s warm waters.
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Main image: Revolutionary poster in Havana (Shutterstock.com)