Yes, I had planned some more tweaks for the game, though I couldn't squeeze our more hours this time. It's a really simple algorithm - one random port of each island is connected to another random island to ensure there is a connection, the other ports are purely random. I had something a tad smarter in mind to ensure you can reach more or less any island with a few hops or so, but I couldn't come up with a solution right away and postponed it.
So indeed you can become stuck on a path that eventually leads to nowhere. Sorry. :) It shouldn't happen that often however.