The quaint, coastal city of Valparaíso, Chile — once an important port town along early South American sea routes — has risen the ranks as a world-class cultural center; its historic district by the sea even became a UNESCO World Heritage Site in 2003. But behind the city’s newfound soft power is an unexpected art form: graffiti. For a closer look, we took a tour with Upscape, which offers bespoke guided excursions across Chile. (Order your copy of Gear Patrol Magazine: Issue 01 for the full report.)

“Graffiti here is still illegal,” says my guide, Rodrigo Javier Torres Aquilar, a 27-year-old history teacher who’s been studying the street-art culture of Valparaíso and the nearby Viña del Mar for the past several years. “You can ask for permission, or make a contract with the owner of a building. But generally it’s not like that. People just paint wherever there is empty space.”

“The best night to paint is Monday,” says Manuel Gonzalez, a 24-year-old graffiti artist living in Valparaíso, who asked that his artist handle not be published. “No one is in the street. Saturdays are bad, for the obvious reasons. People are out, cops are watching.” The fine for getting caught is close to $300 USD. When I ask if he’s ever run from the police, Gonzalez smiles and shrugs. “I’ve been fined three times.”

“If you talk to someone, and you tell them that you’re painting something beautiful, they generally have no problem with it,” adds Gonzalez. “People don’t understand bombs and letters. Letters are also art, but the people here prefer things they can understand. That’s why I paint faces.”