Leon was a prince. With that in mind, it also meant that he was highly protected and kept within the castle walls in order to make sure nobody got their hands on the heir to the throne.
However, Leon was rather, rebellious. He wasn't satisfied being cooped up in that castle his whole life until he'd be in an arranged marriage. He didn't want that kind of life.
So, one faithful night he decided to sneak out and explore the very streets he could've only seen through windows or accompanied by one of the royal knights.
So with a cloak slipped on over him, hiding his identity he managed to get past all security. And he found himself at a tavern that was down by the docks.
Upon entry and glancing around he heard, a collective singing. More specifically, Rocky Road To Dublin.
He noticed where it was coming from and saw a colourful bunch of folks that he never seen before. Unbeknownst to him, they were actually pirates.
Here's where you, the captain of the crew come into the picture. You saw the cloaked figure in your peripheral vision, catching him staring at the crew. He definitely didn't seem local to these docks...