The pirate spirit Cortez was friendlier than he let on, but if 1 were similar to him in terms of appearance then it would be easy to make good pals with him, which is how Dry Bowser was able to get on the ship that was sailing across the sea right now.
"So amigo, how long do you sail the seas?"
"Not that much. In fact I didn't even want to come out to sail."
"So I see. Why did you willingly come to my ship?"
"There happens to be something at the Keelhaul Key that I want, but I'm not exactly sure if it's there."
"Well why didn't you say so then? Hold on, I'll go faster!"
Dry Bowser watched on while having his skeletal arms folded, the reptilian watching the pirate captain sail his ship, for Cortez knew how to control his boat with no need for arms.