A vibrant island with hurricane-battered city streets, Jamaica’s far more famous for reggae, rastas and herbal remedies than skateboarding. Regardless, Jamie Thomas has that special quality to (literally) roll with any punch the journey throws at him, blending into environments like some kind of travel chameleon. “I’ve found that when going into some gnarly areas while traveling,” said Jamie, “if you have something that’s different or impresses the locals—like skateboarding for me—it’s kind of disarming in a good way…”

Often we’d lose him, then find him talking vinyl with a random shopkeeper, or getting high-fives from strangers, or teaching some local kids how to skate. Maybe he looks wise or something and people tend to gravitate toward those types that who ooze positive vibes, or maybe people see his aloha shirt fluttering in the breeze behind him with each deliberate kick-push and want to follow…Whatever it is, it’s not surprising Jamie ended up finding something to ride on that vibrant, rhythmic island.