International Skateboard Mission: Havana, Cuba

cuba skateboarding
Ariel Gomez Lago and Orlando "Orly" Rosales are helping keep the skate scene alive in Cuba.Photo Credit: Skyler Wilder

Greeted by the sounds of skateboards outside my window and then the ring of the doorbell at 11 a.m. in Havana, Cuba – it was time to begin my “Day in the Life” with the guys from Cuba Skate.

After signing up for the trip through Airbnb Experiences, I flew 90 miles south of Florida with 50 pounds of skateboard gear to give away to the locals. Now, the time had come to hit the streets, experience the Cuban skate scene and support some of the local kids in the process.

skateboard Cuba
Skyler Wilder

Skateboarding is on the rise in Havana, and Orlando “Orly” Rosales, 28, and Ariel Gomez Lago, 28, work with the nonprofit Cuba Skate to keep it growing. We were en route to Orly’s home for the first stop of our mission. We skated up the side streets, grabbed fresh juices on the corner and caught a classic 1960s car for a cab ride across town.

After hopping out of the cab we skated past the Tulipan Market, one of the largest in the city. While we all drank a quick cup of coffee, Ariel greeted a friend passing by while I gazed at the dozens of vendors selling cultural crafts and all flavors of food. We proceeded past to bomb a hill with all our goods in hand before reaching his home by noon.

The house, like every other in the neighborhood, had a fence around it and a gate to be unlocked before entering the front yard. We traversed around to the back of the home where Orly had a private room that we bunkered down in, out of direct sunlight, for a few hours. As we drank more coffee and ate bread, we all compared childhood skate stories and spoke about everything that has changed over the years in skateboarding, from magazines, to videos and photographers, spots and the skaters themselves, our conversation covered it all.

skateboard Cuba
Skyler Wilder

They also told me stories of professionals that had traveled over to link up with them and how they have been receiving small amounts of support from the industry in the States. As it stands now, they have zero access to new skate product in Cuba without outside donations. Other aspects of the skate scene were also explained to me, such as their fraught relationship with the local police.

Just two nights prior they had watched their friends get picked up off the streets and carted off to jail for the night, all without any warning and essentially zero discussion. The following morning they were released and issued tickets with fines they were not capable of paying. The guys explained that for locals they can often find themselves being harassed by police enforcement when skating at night or in public spaces. They also explained that these occurrences never happened to tourists.

After many topics of conversation, we tinkered in a backroom where they woodwork and craft with old, recycled skateboards as well as create new boards from scratch. They had blank maple plies, an air-suction operated press and a couple examples of different skateboard shapes they had already made. On the spot they made me a piece for my keychain and a bottle opener from old skateboards. They also gifted me a few photographs, a souvenir Cuban flag and a copy of the ‘zine their nonprofit created to explain the realities of their skate culture.

skateboard Cuba
Skyler Wilder

Around 3:30 p.m. we decided to gather up some of the product and skate down to a park and plaza nearby. There were 16 skateboard decks, sheets of griptape, 5 sets of wheels, 10 shirts, 3 hats, 15 sets of earbud headphones and a stack of stickers and magazines all up for grabs. (A huge thanks to everyone that donated new and lightly used product for this trip: Elliot Sloan, Chris Cole, Dew Tour, TransWorld SKATEboarding, Fred VanSchie and Kent Vogel.)

When we got to the plaza there were about 15 kids already skating. The ground was rough but the plaza had it all from stairs, ledges, handrails, gaps and even a flatbar that was being sessioned.

After a couple hours of skating it was getting dark, so it was time to toss out the product to the kids. Games of S.K.A.T.E. and best trick competitions were had on different obstacles. By 8 p.m. it was winding down and everyone had some new gear on their way out of the plaza.

As I prepared to skate back across town to retire at my Airbnb for the night, the guys invited me to meet up with them the next day. We hopped on city buses and visited a D.I.Y. skatepark they had been creating inside an abandoned gymnasium building.

The place was covered in graffiti, overgrown with tropical weeds and packed with kids skating on freshly poured spots. Ledges, quaterpipes, rails and pump bumps connected all of the rooms in this skate haven which had become the center for skaters in Cuba.

Another day of skating and donating eventually came to an end but we had more plans ahead to take us into the night. Orly and Ariel met me back at my place that evening around 9 p.m. to check out a skate-inspired art show taking place in Old Town Havana.

As we arrived, the show was coming to a close and the streets were beginning to flood for a march or “Art Walk” through the streets before ending up at an empty warehouse. With only a stage on one far-end of the large, single room and two drink refill stations, the warehouse was quickly packed with people purchasing cups at $1 for a night of endless rum and live music until 3 a.m.

Once the after-party for the art show was over we said our goodbyes in the street to conclude my second full “Day in the Life” with the guys from Cuba Skate. It was an amazing trip that will never be forgotten.

For skaters interested in traveling to Cuba to skate and support the scene, you can sign up for a “Day in the Life” on Airbnb Experiences or a D.I.Y. build with the guys from Cuba Skate.

skateboard Cuba
Skyler Wilder

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