Tours,  Travel

The raw guide to Havana: romance vs. reality

Havana is most likely where you’ll start and finish your Cuban trip. It’s the capital of the island and it’s fundamental that you visit. It’s entirely oxymoronic, just like the rest of the country, and you’ll either love it or hate it. Either way you need to understand it for the purposes of, if nothing else, managing your travel expectations. Havana isn’t just colour and romance – there’s a very ugly reality behind it. 

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I hated Havana the first couple of times I was there. Once I’d spent a few hours mooching around the Old Town (Habana Vieja), unsuccessfully dodging the abundant touters and scammers – not to mention the overly confident Cuban men chasing me down the street asking to marry me – I was exhausted and disappointed. From my little research that I’d done before my very first trip, based solely on the romanticism of the LonelyPlanet guide book and those endless filtered Instagram snapshots, I’d envisioned a city lathered in nothing but colour, music, rum and good vibes. Whilst each of those things definitely play their part, there’s far more to it than that.

As you meander the so-called ‘beautiful colonial’ streets, you’ll realise the buildings are crumbling and might tumble on you at any moment. If you look closely, you’ll see locals living in total squalor – their home might not even have a proper roof. You thought you’d be breathing in the sea air direct from the Malecon, but instead you’re filled with suffocating car exhaust smoke from the 1950’s classic American cars rattling down the pot-holed streets that never get fixed. Aside from the architectural hodgepodge, you’ll be faced with limited & expensive internet, pushy and desperate locals, scarce toilet paper that won’t be kind to your culo, electricity and water cuts that last hours at a time, extravagant and tiresome scams… I could go on.


Well, don’t let me put you off Havana entirely: the rumours of Old Havana’s romantic visage are not without truth. The capital has benefited hugely from the UNESCO restoration funding which has been mostly injected into the Habana Vieja district, though with some obvious exceptions. The stark contrast between the crumbling ruins and the freshly restored plazas is remarkable, and is the backbone behind the romantic daydream of the city was just fifty or sixty years ago. The severe urban decay is, sadly, as enchanting as the restoration; the ruinous buildings bring the difficult past of the city to the forefront of your imagination, and you can so easily lose yourself in the heady air as you’re transported momentarily into this other world. 

The colorful streets are brimming with noice and vibrancy. From the revamped cars to the locals trying to earn a living, you won’t be short of things to look at. It’s a fascinating and incredibly unique city, and it’s well worth the effort to explore. 


I personally want to ask to one favour: remember that you’re not visiting a Hollywood film set. This is real life. Cuba is so often idealised by outsiders as being untouched, simple, stuck in time. But really, trapped is a better word. The island has an ugly reality that is so cleverly masked by travel agents and Instagram influencers painting their filters over the oppression, but if you’re visiting this unique island, you should understand the reality of why this island is so unique, and not just get swept up in the romance or the novelty.


Simply put, nobody could have invented a city like Havana. It’s too audacious, too unique, too overwhelming and too complex to ever understand. It’s almost as though it has inhaled the long history of colonialism, piracy, mobster rule, revolution and embargo, only to exhale a survivalist spirit in to its culture and its streets. And so, if you bring one thing to Cuba, let it be an open mind. If you’re anything like me, you’ll leave with more questions than you will answers, and you’ll soon be back for more. 

Further reading on whether or not you’re right for Cuba: click here 

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Raw Guide to Havana - Cassie in Cuba

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