Somewhere in Havana, Cuba, teens are grinding the rails on American skateboards—even though there are no skate shops on the island. The exchange of skateboarding equipment started informally, after Miles Jackson and Lauren Bradley saw a desire among youth for the sport while studying abroad in Havana. They formed the organization Cuba Skate, with the aim of growing and supporting the Cuban skateboarding community by providing access to equipment. We spent a few days alongside Cuba Skate to uncover the roots of Cuban skateboarding and the passion that helps bridge the cultural divide.