Traveling was becoming easier by the day.
When crossing oceans, "distance" could be negated. Unfortunately, this strategy only worked if one knew one's destination exactly, so it wasn't practical for a journey like this one.
On the second island, people walked. Here, there was more development and change so people had vehicles and mounts.
It also became more possible to traverse the lands by canceling distance in increments. Because there were always small towns within sight, one could go from place to place and make judgements more easily.
It was the benefit of a populated island.
Nevertheless, Damien didn't cancel distance to move. It was the most similar method to teleportation, so he could use it more efficiently than the average person, but it was also too much work.
Why would he take the difficult approach when there were far easier methods?