Depends how long you're there for. My cruise ship got re-directed to Ochos Rios which was sketchy, locals were very friendly they love tourists. Was only there for a day so besides waterslides and college girls at the bar, skating wasn't really an option.
They LOVE Marley, he's everywhere. Jamaicans would be stoked if you played Marley. Very good food in Jamaica too, like really, really good. I'd say if you're there for a few days don't bring your board, couple weeks I would. Skating is not a thing in Jamaica, so unless you like waxing shit and skating alone there's better things to do.