This is simply not a spoiler because this clown should be at his ship. I had to go to the mainland for a quest and now I need to go back to the Dragonborn Island but his deckhands say I need to find him. WHAT THE FRIG FOR?! HE SHOULD BE AT HIS SHIP!

So now I have a DLC that is not completable because the NPC needed to go to the area needed has dropped off the face of the game. Awesome!

If you've already been to the island then there should be a fast travel marker on the edge of the map for you to click on to go back. Doesn't fix your problem but it does let you continue playing.

Thank you so much, I'm not a fan of the fast travel but it seems to be the only way for this one. I've spent all time searching for him in Windhelm but couldn't. Even after picking locks.