The streets of Cuba.
The streets of Cuba.
Image: Dan Calderwood

From you first taste of the iconic El Floridita daiquiri at the L-shaped bar Ernest Hemingway frequented, to the ever-insistent bici-taxi peddlers shouting at you, “Taxi amigo! Taxi!”, Cuba offers the kind of delightful chaos that every traveller is seeking.

In Centro Habana, tucked away behind the façades of peeling pastel paints, the ringing of a home landline instantly takes me back to my childhood. There is a familiarity to Cuba but also a mystery. A sense of nostalgia.

Everyday activity spills out onto the streets and the colourful lives beyond open front doors are on full display. Family privacies here aren’t hidden behind 3m-high walls.

As I darted through the morning shadows that were cast along the grid of deep urban canyons, I saw portraits of young girls in bright neon tulle hanging in living rooms. Almost purposely displayed in full view, the princess-like quinceañera dresses offered a stark contrast to the paintings of revolutionary heroes punctuating public spaces. Both, I guess, a simple reminder of how immensely proud the Cuban people are.

A TRUE PICTURE

It’s been written a hundred times over that Cuba is a true travel icon, and I’d been wanting to go for as long as I could remember. Ahead of my three-week trip I carefully curated a collection of inspiring Instagram photos. After visiting, those images reminded me of how others had crafted their memories and presented them within a controlled feed of what they perceived Cuba to be. In some way this is no different to what you’re reading right now.

Walk down any street in Centro Habana for an uncensored step away from the main tourist block in La Habana Vieja.
Walk down any street in Centro Habana for an uncensored step away from the main tourist block in La Habana Vieja.
Image: Dan Calderwood

With so many social media-influenced expectations, I had built up this fantastic idea of what my Cuban experience would be like. It is much more than a daydream come true. One simply wants to photograph everything — the beauty and the decadence, the smiles and the cigars, and all the cars. It’s a challenge to try and look beyond these 1950s American classics. Without sounding clichéd, it really is like being on a movie set.

There’s a strong sense of community and resilience every-where you go on the island. There’s also a warming familiarity to people’s faces and a laid-back way of doing things that I am immediately comforted by. Like that nostalgic echo of a landline, Cubans value personal interaction over the reliance on technology to communicate and get things done. It’s a wistful echo of my childhood in Zimbabwe, and yet so far from my current reality in New York. Nostalgia aside, Cuban society is embracing a new era too. Their oldworld way of doing things is starting to clash with the availability of technology playing out right in front of you. Forget trying to “see Cuba before it changes” — the change is underway right now.

HOME COMFORTS

As part of our visa issued under “support for the Cuban people” we opted to do as many homestays as we could. Airbnb is searchable within Cuba but you can’t reserve and book inside the country.

On our return to Havana, following trips to Viñales and Trinidad, we hadn’t booked somewhere to stay. We had, however, read in our well-thumbed Lonely Planet about the “super helpful, mine-of-local-information” hosts Julio and Elsa at Hostal Peregrino Consulado, where they have a “growing web of casa particular accommodations”.

We decided to trust the system, head to Havana, and see what happened. We’d been in Cuba long enough by then to know that whoever you are, people will make a plan to help you. If it involves tourism and business, you’re guaranteed to be reliably cast into a ready-to- receive-you network.

The streets of Cuba.
The streets of Cuba.
Image: Dan Calderwood

“They are a lovely couple, they have been friends of ours for years, they have a room and can take you.” Elsa assured us as she hurried us out of their lovingly worn and busy casa particular.

With one quick phone call, your hosts could rustle up a family member, friend, or neighbour to do just about anything to ensure the most hospitable stay. And that includes sending you on the back of a son’s motorcycle to a nearby farm to wake up the owner, after after his particularly festive Navidad celebrations, to buy unbranded, non-government cigars in bulk.

Arriving at our accommodation, we were greeted by a retired Cuban doctor who’d spent six years lecturing at a training hospital in Mthatha. We could not believe that of all the homes we could have stayed in, we walked into one of someone who knew ours so intimately. A dolphin “snow” globe proudly labelled “Durban” sat perched on the bathroom windowsill as we freshened up. “This was given to me by a friend when I left Umtata,” the doctor said, carefully holding out a carved walking stick as his eyes glossed over while recalling his time in the Eastern Cape. “I’ve been hoping for a visitor from South Africa for so long. You’ve blessed me, you’ve made my year!”

OFF THE BEATEN TRACK

There is not much for the traditional tourist to do in Havana’s Regla borough, but just a short ferry ride on the eastern side of the city’s harbour, it has another flavour of life and is somewhat untouched by visitors. As the sun reaches its peak and the streets empty of people to photograph, I find myself outside a busy barber shop. Gestured in to have my hair cut, I choose to rather have my beard trimmed, as seems to have become a regular travelling tradition.

Outside the 1940s Teatro America.
Outside the 1940s Teatro America.
Image: Dan Calderwood

Sat among trendy locals, some in their early twenties with torn jeans, perfectly shaped eyebrows, and glitzy diamanté earrings, I observe the comradery and the habitual grooming routines of the men coming and going. Havana men take their haircuts very, very seriously. They like to sport the latest trends. It’s a well-loved way of expressing themselves and “for the ladies”, as one particular muscular, tattooed barber tells me.

A heavily persuasive reggaeton beat accompanies my silent conversation with my barber as we type into his Google Translate and share the screen. “Cuba poor. No dinero here! Trump bad; Obama better,” he smiles with a mouthful of gold teeth.

AT SEA

All roads in Havana lead to the Malecón, the wall and promenade that run along Havana’s coastline, facing towards the United States. Just before Christmas, a cold front had caused massive waves to crash over the seawall and the water had reached blocks inland. The adjacent six-lane highway had to be closed.

Under the afternoon glow, buskers line up like jukeboxes, waiting to slowly lure innocent tourists to pay 1 CUC before they unveil their automated rendition of Despacito. Two lovers fold into each as the fresh breeze relieves them from the soporific heat.

A fisherman sporting a “Too broke for Supreme” t-shirt casts out over the rocks below. The waters surrounding his empty keep bucket are a clear, sapphire blue.

Enjoy cooler evenings on the Malecón as fishermen gather.
Enjoy cooler evenings on the Malecón as fishermen gather.
Image: Dan Calderwood

As the sun drops, families line the wall. Vibrant laughter breaks through the constant chatter. I can make out some French tourists, but mainly the characteristic Cuban Spanish dialect.

Dubbed “the world’s longest sofa”, it almost feels like the whole city comes to meet along the Malecón. Together we watch the setting sun cast its last millennial-pink hues above the Caribbean. The elevated 17th-century fortress guarding the entrance to Havana’s bay is the perfect frame for endless selfies.

Visiting Cuba for the first time gave me a sense of freedom that I had forgotten about. Being free from modern-day pressures of an overconnected society felt liberating as I observed people living a more “simple life”. I saw a nation that spends quality time with one another through engaging conversations instead of burying their heads in technology.

Living in a Communist country, the restrictions Cubans experience would make most believe they have no liberty — but in fact, that might be the very reason they experience a freedom in a way we, the rest of the world, don’t.

Until next time Cuba, la cuenta, por favor.

Calderwood is a Zimbabwean/ South African photographer and journalist living in New York City.

From the August edition of Wanted 2019.

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