Magic Ship: The ship is certainly magical, as is one of its inhabitants. Can you decide for yourself if he is the captain (like Davy Jones) or is he just the captain's tame animal that he sets on enemies? Also, at your discretion, the purpose of the device at the very top of the ship. I assumed that this allows the ship not to sail, but to fly over the water at a low altitude. You can also consider the option that it creates an invisibility field, this will allow the ship to sneak up on other ships, or you can come up with something of your own.
Small ship: A small merchant ship, or at least it tries to appear so. What makes it stand out among others? The captain playing the violin? So different in character, but loyal senior assistants? Or maybe the cargo that is in the hold? It's up to you to decide. When creating the map, the following assets were used: Forgotten Adventures, Tom Cartos, White Fox Works