The immediate follow-up is to guess “Italian?”. I’m bemused – Cuba is not overflowing with Italians and I’ve never been mistaken for one in the past. “England,” I reply dismissively, having learnt this oft-repeated conversation is only a question or two from a sales pitch for bootleg cigars, a woman, a taxi, or often all three.

“Ah, England!” the hustler adds excitedly, then adds, “Ali G! Booyakasha!” and flicks his fingers together in the air before returning to his corner. In Cuba it seems, even the cultural references are stuck in a time warp.

There is nowhere else like it in the world, though. It’s where Latin America meets the Caribbean, a place where the sounds of rumba, jazz and reggaeton are always within earshot and where rum is not just a drink, but a way of life. And, yet, what really sets this largest of the Caribbean islands apart is its politics. One of the last real bastions of communism, Cuba is both the oh-so-close thorn in America’s side and the land responsible for creating the icon that is Che Guevara. It’s also a place where, in many ways, the clock simply ground to a halt when Fidel Castro’s rebels sweptto power in 1959.

Rum diaries

But communism and clocks aside, my plan is to live as the Cubans live, to follow in the footsteps of the pirates and the planters, by letting the rum dictate my days – I’ll be working my way around the cocktail list as much as the country.

After all, considering Cuba once led the world in sugar production, it’s unsurprising the country is also the birthplace of the world’s best rum, not to mention most rum-based cocktails. The trailblazer was the Bacardi family, but they’re based in the Bahamas nowadays, having not fancied Fidel Castro’s business plan. Now, the one brand in town is Havana Club. Luckily enough, it’s no poor substitute.

Revolutionary road

My first day in Havana is an onslaught on the senses. Boys strum guitars in doorways, the sound of a solitary clarinet drifts across an empty stadium and an old man blows soulfully into a French horn towards the watery horizon. I walk through the heat, the searing heat, towards the postcard-perfect streets of the World Heritage-listed old town, sweating my way along the Malecon, the majestic surf-battered boulevard that sweeps along Havana’s brow, its ocean wall dotted with couples and drinkers, all looking out to Miami, all dreaming. 

The roads are a cacophony of cultures, with just about every passing vehicle feeling as though it began life elsewhere. There’s the bicitaxis and tuk-tuks so reminiscent of Asia. Around them scoot the masses of Russian-made Ladas. And, of course, representing Cuba’s BC, as in Before Communism, are the classic American cars. Chevrolets, Fords, Dodges, Buicks, Cadillacs and more, each dating from the 1950s or earlier.

God knows how many times they’ve been rebuilt from the inside out, but these hulking American giants chug past continually, belching out fumes while effortlessly creating an old-world glamour I’ve not experienced outside of a cinema.

And then there are the buildings. Crumbling grandeur personified, a reminder of a different age, a time when Cuba was a Spanish colony and the powers that be took great pleasure in frittering away their vast slave-driven sugar riches on architecture of the highest standard. 

The city is like a broken honeycomb, with brightly coloured facades giving way to grey ruins, whole floors exposed to the elements where neighbouring buildings have collapsed. In places it feels as though Havana has endured some terrible bombing, but time and a lack of money have been the only enemies here. It’s a city with museums and monuments and castles as good as any other, but Havana itself is the ultimate living museum. 

Mo money, mo Mojitos

The heat is oppressive and inescapable, but I discover a cure. Perhaps Cuba’s most famous creation, the remedy is a mix of lime juice, sugar, sparkling water, mint and white rum – it’s the Mojito. Dating back to the 19th century, some believe the drink evolved from a previous cocktail known as El Draque, named after English seaman Francis Drake, forever the curse of Spanish defences. Others believe African slaves working in the sugar cane fields came up with the drink. Whoever it was, with my head light and body refreshed, I owe them a debt.

Days pass as I wander the streets, taking refuge only to refuel on Mojitos, returning home only to recharge my camera, and before I know it, I’ve lost a week to Havana’s sweltering streets. It’s time to explore the country. And the cocktail menu. 

I’ve got a fortnight, ample days for a loop of the country’s west, and so board a bus for Santa Clara, the epicentre of Cuba’s Che worship and the promised land for beret-wearing students the world over. Out on the open road, like in the city, there is no advertising. Except for the ideas of the state.

“Fatherland or death”, “Until victory, always” or simply “Socialism!” scream the slogans printed across buildings and billboards, looking more like youthful graffiti than the propaganda of a 50-year-old regime.

After a few hours of lush countryside and political education, we arrive in Santa Clara, where it’s soon clear that life outside Havana moves at a slower pace. For starters, horses and carts are almost as common as cars.

Santa Clara was the scene of the revolution’s decisive battle, and it was won in large part by the daredevil leadership of Comandante Guevara himself. Here, with just 18 men and an armoured tractor, the A-Team would’ve been proud of, he managed to derail a military train, defeat the 350 troops on board and subsequently inspire the government soldiers to surrender the whole region.

President Batistuta duly fled the country 12 hours later. The remains of the train, reminiscent of a Bond set, now form an interesting museum, while a giant monument to Cuba’s favourite Argentine (that’s Che) has been built on the outskirts of town.

As such, a change of refreshment in favour of something more revolutionary seems imperative, and so I leave my beloved Mojitos in favour of a Cuba Libre. Actually nothing to do with Guevara’s liberation of his adopted homeland, this cocktail, essentially a rum and coke with lime, earned its name 60 years earlier, when Cuba gained its independence from Spain. 

The liberation party was clearly a long one, as Coca Cola didn’t arrive in Cuba until 1900, two years after the US had helped chuck the Spanish out. But more than a century later, it’s still an apt label, as it’s the easiest DIY cocktail on the road, thanks to my $3 bottle of Havana Club, even if I must make do with cans of communism-friendly TuKola, rather than the original coke.

Up in smoke

Now overflowing with revolutionary spirit, it’s time to head onwards, towards the south coast and the World Heritage-listed town of Trinidad, which is that rarest of things – a much-hyped destination that delivers what it promises. 

The main square is straight out of a period drama, bursting with colonial buildings and cigar-smoking characters. It’s a town so charming it feels like the setting of a fairy tale. Mornings are filled with horse riding trips to waterfalls in the surrounding mountains, the afternoons spent driving to the beach in classic cars. Evenings are for the next on my cocktail list – the Daiquiri. 

Like both the Mojito and Cuba Libre, the central ingredients are still rum and lime juice, yet the Daiquiri has just one extra flavour, a dash of sugar syrup. Delivered in a cocktail glass, it’s the epitome of old-fashioned elegance, making Trinidad the perfect place to sample one. With little to dilute the rum, they also leave my head spinning, causing me to stumble home through the cobbled streets.

The next morning, my eyes still blurry with Daiquiries, I start heading west again, venturing beyond Havana to the tobacco country of Viñales for my final stop.

Steep-sided dolomite hills rise sharply out of the lush plains surrounding the town, offering welcome shade to the sombrero-clad farmers who take a break from their toils to suck on the region’s world-famous produce. After all, from Cohibas to Montecristos, this is where many of Cuba’s cigars begin life. If Trinidad is the pin-up star of Cuba’s preserved architecture, then Viñales gets the tiara for hands-down natural beauty. 

As such, I’ve got one heavyweight cocktail left to try and this place seems as good as any. The drink is known simply as the Hemingway and it takes its name from the cigar-loving writer who called Cuba his home for decades. 

Based on the Daiquiri, The Old Man And The Sea author added grapefruit juice and maraschino liqueur, plus doubled up the rum. It certainly doesn’t take many of them to appreciate its creator’s infamous self-destructive qualities. Fortunately, the size of Viñales makes the now customary stagger home mercilessly quick.

And so, another hangover, another bus, another call of “what country?” and I’m back in Havana, my tour of the time warp complete. Well, not quite. Maybe there’s time for one more Mojito… 

Currency: AUD$1 = CUC$0.9. Cuba’s dual currency system means whatever the price, tourists must generally use Convertibles (CUC), which are worth the same as the US dollar. Locals use Cuban pesos, worth almost 30 times less. Changing CUC into pesos is quite easy, but most official places (museums, Viazul buses etc) will insist you pay with CUC.

Getting around: Tourists are kept together on Viazul buses ( Save cash and forfeit comfort by jumping on a non-tourist bus. To do that you’ll have to change your CUC into Cuban pesos.

Accommodation: Casa particulares cost on average CUC$25/night 

See: Lonely Planet’s Cuba

A Family Affair: Mi casa es tu casa

The tightly controlled nature of the Cuban economy means that basically all hotels are at least partly state-owned. More often than not, they’re run-down and overpriced. Backpacker hostels don’t really exist in Cuba so your best bet is a casa particular. These are small guesthouses where families have secured a licence to rent out one of their spare rooms.

The rooms, which normally sleep two to four, are about $25. Most casas also offer huge, tasty home-cooked dinners, which are reasonably priced (expect to pay $8 for meat, $10 for fish or $12 for lobster). Bear in mind you might find yourself going cold turkey from the internet while in Cuba. It is available, but generally involves long queues, painfully slow speeds and high prices.

As such, if you like to plan your accommodation, do it before you arrive. Otherwise, guidebooks like Lonely Planet list their favourite casas or simply knock on a door bearing the blue anchor symbol that means they take tourists (an orange anchor means they’re a casa, but for Cubans). Your best bet is often to get your current host to recommend and book somewhere at your next destination. 



Photos: Andrew Westbrook; Thinkstock; Getty