No no, you're thinking of circumvallation. This is about sailing a ship all around the Earth.

It's missing one of those sharpie additions, like the hurricane Dorian map one, to feel really authentic

If you are happy with Debian, I'd say stay with it. I have tried many distros but I like Debian and return to it for most of my devices. Sometimes Debian will have older versions of software if you use stable, I don't really mind personally