As I and others have said, IF there's no one there too oversee him, to chaperone him, he will be afraid to go out of his room much less get off the ship and explore the town. (And there's a lot to do ashore in Nassau..etc. but he will do NONE of it.)
It's been noted a million times, but it always takes me aback but doesn't surprise me in the least. He doesn and has had great opportunities to travel, to report, to experience new places and things, but he's a fearful and paranoid mentally stunted little guy who is what he is at 30. So much has passed him by. Even park crawlers like JoJo have traveled the world, in one year to China, England, France, Singapore, the Middle East and on and on, while Kyle begs for little cruises to the Caribbean isles next to Florida. He's content with that, but fears doing even that ALONE.
So on one more tiresome and dull damned mini cruise, he's afraid by himself and bored and drinking heavily. So he does what he does: He wastes time and energy 'owning the hatters' because it seems to give him some perverse pleasure but is ALWAYS a negative for him and ends putting him and that dumb Doormat in jeopardy in that little house.
It's sad and pathetic but he's locked in and he can't get out. He can't face what a failure he is and so his little failing
tit show stumbles on, enabled by his weirdo parents and sister.