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Consider the most 'historic' cities around the world and the first images that are likely to spring to mind might be of the coliseum in Rome, the Acropolis of Athens or the tombs of Petra. But history need not always be of the ancient variety, in fact there are few cities around the world in which so many layers of a city's development can be so vividly seen and experienced as in Havana.

Cuba is a country built on colonial foundations, influenced by African slaves, indigenous Caribbeans and by the governments on both sides of the 20th century Cold War divide. All of this cultural heritage is mixed together in Havana, often overlapping, contradicting each other and adding to the rich tapestry of one of Latin America's most exotic cities.

If you've travelled with Veloso Tours before, you'll know that we are never satisfied with typical run of the mill city tours, postcard snapshots and tired cliches. So let's dig a little deeper to give you a deeper perspective on the Cuban capital to perhaps inform your own travels here in the company of our friendly guides.

1. Explore Colonial Cuba in Habana Vieja

One of the great fallacies of history is that the Genovese explorer Christopher Columbus discovered America. He never actually set foot on the landmass we now know as the USA and only briefly landed on South America and Central America on his third and fourth voyages respectively. What he did 'discover' is a reliable and safe route to the hitherto unknown Caribbean Islands, particularly Haiti, Jamaica, the Dominican Republic and Cuba. Upon landing on Cuba, Columbus convinced himself that he had landed on the gateway to China and the Kingdom of the Grand Khan, as referenced by Marco Polo in his extensive travels.

The Spanish eventually settled Cuba, establishing seven cities, of which Havana was one. Since then, the city grew in size, prosperity and importance and today the evidence of said wealth remains wonderfully in-tact. Our colonial walking tour of Habana Vieja (old town) links four squares in which we find a wealth of beautiful architecture and magnificent Catholic churches, whilst the Palacio de los Capitanes Generales is a wonderful place to gain an insight into the opulence of the era.

2. Gain a fuller picture in Havana's other neighbourhoods

Our story develops with a panoramic car ride around some of the areas missed out by many casual visitors or day-trippers in Havana. Across the water is the old fort - built to protect the city from English incursions, whilst in the upmarket neighbourhood of Miramar we find grand mansions confiscated by the Revolutionary government of Fidel Castro and now living second lives as national embassies. Parque Almendares is known as the Forest of Havana and provides a glimpse into how the city might have looked many centuries ago. Today it is also often the sight of religious santaria ceremonies.

One of the city's most iconic sights is the wide waterfront avenue of the Malecón, particularly impressive at sunset, but there are many other reasons to visit the neighbourhood of Vedado. This largely residential area is home to the iconic Hotel Nacional, the breathtaking Colon Cemetery and some of the city's best live music venues, not the least the Fábrica de Arte Cubano and the Patio de la Rumba (see below for more).

3. Delve into Cuba's revolutionary history

The roots of Cuba's unique society in the 20th and 21st century can be traced directly back to the period of revolution in the middle of the last century, when Fidel Castro, Che Guevara and a relatively small band of guerrilla fighters took on and defeated the US-backed Batista dictatorship. The fallout from this period left an indelible mark on the country, which defines how Cubans live today.

The rising tensions at the start of the Cold War left Cuba politically isolated from the rest of the Western world and the failed Bay of Pigs invasion pushed Fidel Castro's government into the welcoming arms of the Soviet Union, precipitating the Cuban Missile Crises. Since then relations have remained non-existent, with President Trump undoing the inroads made by the Obama administration.

Havana is one of a number of places in Cuba where you can piece together the development of this epic story. At the excellent Museo de la Revolucion, housed in the grand former Presidential Palace, you can learn more about the people and tactics involved and see for yourself some of the vehicles and weapons used. The Plaza de la Revolucion is a sweeping public space defined by the immense metal outlines of Che Guevara and Camilio Cienfuegos, as well as a memorial to Jose Marti - the iconic hero of the first revolutionary war to rid the island of Spanish control. 

4. Find traces of American cultural influences

One of the many contradictions of Cuban society is that several leftovers from the US era of excess and exploitation remain so vividly central to the Havana experience. Take Ernest Hemingway for example, who could easily be defined as part of the old 'capitalist' establishment in which inequality was rife and Cuba was largely seen as a playground for rich Americans and gangsters. Today he remains as celebrated as ever, with bars like El Floridita and El Bodeguita del Medio and the Ambos Mundos hotel still living largely off the glory of his frequent visits. The Hotel Nacional in Vedado is a stately monument, whose Art Deco features hint at its past as the focus of the US tourism trade and its dalliances with mobsters.

One of the Cuban cliches that most holds true today is that there are indeed gleaming classic American cars everywhere. Cadillacs, Chevrolets, Fords, Buicks and Chryslers stand wing mirror-to-wing mirror, jostling to catch the eye of visitors, ready to whisk you off for a pleasure ride along the Malecon. Around Parque Central is perhaps the easiest place to catch a ride, where you can also see the Capitolo building, modelled on the White House in Washington.

Beyond the cars and the cocktails, other remnants of US culture remain deeply ingrained in Cuban life, not least the national sport baseball and the cabaret performances enjoyed at Tropicana.

5. Get to know Cuba's African roots at Patio de la Rumba

Before the American's arrived, Cuba's society had already been injected with an array of cultural influences from the slave population which was brought over from Africa by Spanish colonisers.

Such was the strict requirement to adhere to the Catholic faith, the growing African population had to come up with their own ingenious ways to worship their own Santeria faith. Each orisha deity was paired with a Catholic saint and worshiped accordingly, in the most clandestine of ways. Over the ensuing decades, this practice remains loosely adhered to and the sizeable African population of Cuba have profoundly impacted the famous melodies which are transmitted around the world from this Caribbean island.

The best place to get an insight into the colour, rhythm and alegria (joy) of this culture is at the Patio de la Rumba, hidden out of sight in a residential street in Vedado. Every Saturday afternoon the place comes alive with infectious drumming, foot-tapping musical arrangements, seductive singing and eye-catching secular dancing. A festive family atmosphere ensues and visitors are encouraged to join in and share a dance with the locals.

6. Admire the handywork of Havana's creative community

Cuba's African influence can also be examined at the spectacular Callejon de Hamel. Inspired by artist Salvador Gonzalez Escalona, this community project injected new life into a small nondescript street in the Central district, providing a space for elements of African culture to be expressed in street art, sculptures and poetry. It is also another excellent place to see live rumba dancing and music, performed on Sundays.

On the outskirts of the city is the surreal Fusterlandia - an extraordinary sight which needs to be seen to truly be appreciated. The brainchild of this was Jose Fuster, deservedly known as the Picasso of Cuba, but it was actually from Gaudi whom the artist drew his inspiration and to whom the area pays tribute. What started as a relatively modest expression of artistic flair grew into something special as more and more neighbours turned their homes over to Fuster and allowed him to cover them in colourful fragments of ceramic tiles. Since then all manor of buildings have been adorned with a ceramic cloak, even the local bus stop. The result is a bizarre, perhaps child-like, fantasy land, with a strong community feel and which leaves a deep impression on any visitor.

7. And then retire to your room at a casa particular

Of course, during your time in Havana you are going to need a good base from which to sally out each day and rest up in at night. Cuba's political isolation has had a rather profound impact on some of its hotel stock, with many of Havana's most famous icons suffering from neglect over the ensuing decades.

Fortunately, the b&b style casa particular revolution has breathed new life into Havana's hospitality industry, offering visitors not only a good night sleep, functioning air conditioning and a reliable source of hot water, but also an experience which will enrich and enhance your stay here. You'll be welcomed with a smile, looked after with care and attentiveness and wake up every morning to a fresh Cuban breakfast, sometimes taken on a secluded rooftop. Some of our favourite options include grand colonial mansions adorned with antique furniture and details and some smaller houses, tucked down sidestreets within a few minutes stroll of Plaza Vieja.

Read more: Mi Casa Es Tu Casa: Cuba's Homestay Revolution

Where to Combine with Havana

From Havana you might like to head east to the fertile Vinales Valley, where tobacco plantations and immense limestone hills define the landscape and where a slower pace of life ensues. Trinidad is one of Latin America's most beautiful colonial cities, with a UNESCO heritage centre full of brightly coloured houses, cobbled streets, lush squares and excellent museums. Nearby is the Sugar Valley, from where the city gained its former wealth, and the Topes de Collantes mountains in which you can hike past impressive waterfalls, go swimming in natural pools and catch glimpses of exotic birds.

Cienfuegos is defined by its magnificent French-influenced Neo-Classical architecture and the glorious sunrise and sunset views you can enjoy from your casa particular on Punta Gorda. Not far from the city is Laguna Guanaroca, where you can see flamingos, pelicans, cormorants and an array of local birds.

You might also like to combine Cuba with the Mayan pyramids, provincial villages and colonial towns of Mexico's Yucatan Pensinsula on our Ambos Mundos tour.

Discover more places to visit in Cuba

Make it happen!

Browse below to view some sample itineraries to Cuba, which can be booked as you see them with updated flights, or we can tailor individual elements to you, including hotels and excursions. Alternatively, we can start with a blank piece of paper and create a holiday centred around your likes, interests and aims.