I have made the trip between Freeport and Qeynos via both Highhold Pass and
the Gorge of King Xorbb. For a Bard, I think it is very clear that the
Gorge is much easier. Once you enter the Gorge zone you only have to follow
the left wall. Put up Selo's and run. That is too easy to beat. Just
don't stop under any circumstances.

Highhold is not as difficult as it used to be because there are often many
high teens and twenties characters, but there are quite a few sharp turns
and if you have any of those chronically lost people in your party, Highhold
is not for you. HHP also has citizens and guards that will help to defend
you, which is its main good point, but for sheer simplicity the Gorge is my
favorite.