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Havana guidebooks are outdated relics that not only relay misinformation, but highlight an insular view of the city by focusing on places rather than interactions. With help from the team at Havana Club Rum, we set out to discover and share the city's untapped, underground subcultures for those wanting an authentic experience from the moment they step off the plane.

Using the city's greatest resource — its people — as our guides, the second installment (check out part one here) of our three-part Havana travel experience focuses on an irrepressible skate community, passionate car owners, a world class boxer, unparalleled nightlife, and a street level reggaeton act looking for recognition.

Unlike conventional “tour guides,” these people are deeply entrenched in their respective communities and provide typically unobtainable insights, taking us from a sun-filled morning on El Prado to the nightlife of Calle Veinte Tres. They share enough information to fill an entire day with meaningful and culturally enriching activities and to help avoid the Cuban clichés such as grabbing a mojito, finding Cuban cigars and planting oneself at a Wi-Fi hotspot (which we'll expand upon in part three).

If you're lucky enough to visit and you're wondering what to see in Havana, check out the real side of it in our video, guide, and map below, featuring five essential activities and must-see destinations.

Witness the skate culture in Paseo del Prado, Central & Old Havana

The Prado runs from the Malecón in the north to a little past El Capitolio and Hotel Inglaterra in the south. During this mile long trek, you're transported from the tranquil seawall to a bustling, urban epicenter where lanes of classic American cars engulf you on either side and noxious fumes of diesel gas replace any cooking smells from local paladares.

Nestled closer toward the urban sprawl is a section of pristine marble and benches—Parque Central—which has become the unofficial home to Havana's bustling skateboarding scene which is still only thirty years old.

Having adopted a "Patinar o Muerte” (skate or die) attitude—a clever play on Che Guevara’s famous rallying cry, “Patria o Muerte” (homeland or death)—games of SKATE never stop. Even if you're not watching, you're still audibly made aware when a trick lands by the dozens of men, women and teens who gladly share in other people's successes.

Our local guide into the skate scene, Yojany, has been skating for 16 years and represents a generation who latched onto a sport far removed from more acceptable pursuits — by government standards — like baseball or boxing.

Like many of the thriving subcultures in Havana, what skaters are doing isn't technically illegal, but it exists in a gray area like tattooing (which is also expanded upon in part two) as "trades" that don't fit the government's standard for proper employment.

"We do our own projects ourselves, because right now we don't have the government support," Yojany says.

While a DIY spirit is certainly instilled in skate cultures all around the world, it is particularly present in Havana's scene.

For almost three decades, skaters have relied on visitors that bring necessary materials like decks and wheels. This was particularly important because there still isn't a dedicated skate shop in Havana.

"Whenever you [broke] a deck you had to place a piece of wood underneath it and clamp it and carry on skating," Yojany says of the old days.

But those days are slowly changing thanks to the ease in travel restrictions — especially for Americans — who often bring extra equipment with them which is then squirreled away by locals for instances when things break.

"We store the equipment so when someone needs it, we share it amongst us," Yojany says.

The Prado itself feels like a skate shop and skate park rolled into one experience. For every person embattled in a game of SKATE, there are also people laughing and listening to music on the side who are friendly and eager to hear about your own reasons for visiting.

For visitors and locals alike, it's also a free activity that is culturally rewarding and represents diplomacy at its finest.

Check out the vintage cars near Estación Central de Ferrocarriles

The moment you touch down in Havana, the aforementioned vintage American cars, all from a bygone era where metal, steel and chrome were prerequisites for design, are immediately striking.

If one felt so inclined to play car BINGO, "red Cadillac," "blue Plymouth" and "white Chevy" would be filled up on your card in less than an hour.

The vintage cars are a byproduct of the 1960 trade embargo between the United States and Cuba that was first enacted by President Dwight Eisenhower and later made permanent by President John Kennedy which would produce a $10,000 USD fine and ten years’ imprisonment to any American individual or business seen dealing with the island nation.

In turn, the American cars that were already in Cuba at the time were the last automobiles which reflected a more harmonious existence between the two countries.

Despite the romanticism for the American relics of yesteryear which have been Frankensteined into working order with motors and transmissions from other makes and models, shampoo used as brake fluid and toothpaste used to buff paint, there is another car with Russian origins that holds a special place for many car enthusiasts: the Lada.

"[It's] the car of Cuba," says Javier, who gathered his car club, Motor Friends, near the Estación Central de Ferrocarriles to illustrate their passion for the Soviet model.

Forged in Russia in the late 1970s, the Lada has become a source of pride for thousands of Cubans who manage to shell out $20,000 USD for a car when the average salary is only $25 USD a month.

"It's the car that usually all Cubans can own for [because] of how easy it is to repair," Javier says.

It's estimated that 250,000 Lada's populate the various cities in Cuba.

While that staggering number may suggest it is not as rare a bird as an American classic, the car owners themselves are the true gems who can turn a simple grouping of cars into an impromptu block party.

In a matter of minutes, neighbors emerged from their houses to see what was happening, kids began teasing each other in the street, and music erupted from a car radio.

And in the center of it all was the Lada. It's beautiful not only for its intrinsic value but for what it means to the Cuban people.

Take boxing classes at the Gimnasio de Boxeo Rafael Trejo in Old Havana

Stepping into Rafael Trejo, the open-air boxing gym named after a Cuban law student killed while leading protests against the Machado presidency in the 1930s, feels like entering a gladiator's amphitheater. It seems far removed from pugilistic imagery conjured up when we think of title fights in Las Vegas.

The red bleachers at opposite ends are weather worn and hot to the touch in the mid-day sun. Outdated punching bags appear to have already been beaten into submission. An overturned, industrial-sized truck tire and a sledgehammer are the only pieces of cardio equipment in sight.

The boxing ring itself is mere feet from nearby apartment buildings where you can hear people cooking, chatting and singing. There's even a rooster nearby, but one couldn't say where for sure.

Whereas these clings and clangs have become soundtracks for Olympic boxers who began training at Rafael Trejo in 1968, so too have the exertion noises of men hitting bags and pads become regular aural accompaniment to those living alongside the gym.

What makes this gym so unique is that regular people can train alongside past Olympic champions like Beijing silver medallist, Emilio Correa, who was there the day we visited.

The son of a Welterweight gold medallist from the Munich Olympics in 1972, Correa's lineage is not solely unique to him.

Havana is a city for fighters — both in spirit and physical form.

"Boxing is the sport that waves the flag for Cuba and Latin America," Correa says. "Under the direction of Mestre Flores, who is our coach, [you get] a very organized and disciplined training method with a strong physical and technical emphasis."

Of the 220 Olympic medals that Cuba has won since the country began competing in Paris in 1900, 73 have come in boxing — with 37 gold — most recently earned by Robeisy Ramirez, Julio César La Cruz and Arlen López in Rio.

Even though it may seem like a nuisance to have amateurs and novices training alongside him, Correa insists that he enjoys it.

"We give everyone who comes here to train a strong discipline, good vibe and a happy environment," he says. "And you will take home a strong Cuban boxing experience."

Party into the early hours at the Rio Club in Calle A Miramar

Like other Latin American countries, reggaeton dominates the musical interest in Cuba (although there is a notable, all-female group carrying the torch for "backpack rap" which we will explore in Part 2).

Since the genre emerged in Puerto Rico, Cubans have adopted the hybrid stylings which mixes Latin rhythms, dancehall and rap.

As with many things that spark the interest of the people and plays up themes involving sexuality and consumerism, the Cuban government weighed in on the music in 2009.

Julian Gonzalez, President of the National Council for Visual Arts, told Reuters, "In the cultural world there is concern about the excessive popularity of reggaeton."

Culture Minister, Abel Prieto, also said that it should be "pushed away."

In 2012, Cuban Music Institute head, Orlando Vistel Columbia, decreed, "There is vulgarity, banality and mediocrity in other forms of music too. But it is also true that reggaeton is the most notorious."

This led to an unofficial ban on the genre in 2012 which promised punishment for people and places who engaged in concerts.

Despite the crackdown, Reggaeton has continued to flourish thanks to an underground system of sharing music called "El Paquete" (The Packet) which relies on hand-to-hand exchanges of thumb drives as opposed to attempting to share music on the Internet which is much more of a hassle.

"That’s how this music has been able to gain such popularity without having access to TV or radio,” said Lisette Poole, director of the short documentary, Reggaetón Revolution: Cuba in the Digital Era.

Our local guides, Popy and La Moda, view themselves as a "second level" Reggaeton act.

"To be a second level Reggaeton act means we are 'urban Reggaeton'. We don't have a musical school and are always fighting [for recognition] because it's from the streets," they say.

The Rio Club—sometimes called "Johnny's" or "Jhonny's"—is the perfect setting to listen to and experience the local Reggaeton scene in Havana.

The club itself has no frills. Once past the bouncer, you enter a large room bathed in neon lighting with an acoustic bounce that makes it feel like someone is punching you in the chest.

The main stage appears to your right. There are tables and chairs on both levels. Nestled in the back is a small bar where Havana Club's rum drinks set you back only a few CUC's and cold beers are so cheap they're practically free.

Perhaps most importantly, there isn't a single tourist in the place. It's full of locals; men with Yonki haircuts and women eager to shake it with little remorse.

In a city full of culture nestled into tiny corners, the Rio Club is a musical standout.

Enjoy local food, drinks & nightlife on Calle 23 a.k.a La Rampa in Central Havana

When visiting Havana, you quickly learn that when asking for a bar or restaurant recommendation from a local, they often tell you what they think you will want to do — as opposed to what they would do with friends and family.

Places like EL Floridita, La Guardia, Fabrica del Arte and Sloppy Joe's will all inevitably come up in conversation. However, if you want to experience real nightlife in Havana, look no further than Calle 23 which colloquially bears the name "La Rampa" because it literally slopes downhill as it passes other notable cross streets like Avenida de los Presidentes and Paseo.

Beginning at the Malecón and ending at the Almendares River, the El Vedado district is home to a slew of nightlife options and notable bars like Pabellon, Tigoba, El Sofia, La Zorra y El Cuervo and La Gruta where you can belly up to the bar alongside Havana residents.

Specifically, the Pabellon plays to more of an art crowd, El Sofia is good for mixed drinks, and La Gruta is for those that want to dance.

Our guide, Francisco, a student, illustrates the popularity of the stretch of bars — especially amongst the locals — stating. "As far as I remember, this has always been a busy street. The locals don't go to Old Havana. They all come here."

Although Cuban salaries don't afford most residents many additional comforts, nightlife remains an integral piece of their everyday existence.

Thanks to the proximity to the Malecón, locals often will pool together their money for a bottle of rum and simply walk the stretch from the ocean to Calle 23. If they feel so inclined, they pop into one of the aforementioned bars.

For those on vacation, this is the best way to experience the drinking culture.

Now check out the portraits we shot with Havana locals for part one of our three-part Havana series.

  • PhotographyAdrian Mesko
  • VideoSantiago Arbelaez
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