The conclusion of my provisional speculations were summarized in the following picture:
In short, his route from Askifou to the place marked with an ‘X’ was easy to figure out. However, from ‘X’ to Anopoli (Riza, to be precise) was not so obvious. The one route that I was familiar with, marked on the map, did not fit his own description:
From this point [i.e., point ‘X’] we continually descend along the side of the mountains, by a very bad road, towards the plain of Anopolis, and we reach its northern edge at half-past one.
I returned to the area a few weeks ago to resolve the problem. This GoogleEarth image gives the places where I took some photos to explain the situation:
Photo 1386, taken close to path down to Timos Stavros, is aimed NW. I identify the road with green arrows, and ‘X’ is same as above. From this distance, and at this time of morning (sun angle) there is nothing to see other than a rocky slope:
I took two zoomed photos taken from same location. Photo 1386a has green arrows picking out walls moving up the side of the mountain:
Photo 1386b, more to the left (west) has more walls marked. Also, notice the impressive fault scarp (the smooth rock face):
Back to Google Earth where I include the track starting at the fault scarp:
Photo 1401 looks up along the track. A bit of the retaining wall can be seen at the upper left, passing through the fault scarp:
Photo 1404 is taken above the fault line, looking back to where photo 1401 was taken:
It is obvious that the track does not exist anymore. Only some of the walls, at some times of the day, are visible.
There is a vague hint of a route branch at photo location 1401. I followed the way down to the left (east), past an old ruined structure at 1410:
This route eventually wraps around the hillside and emerges at the structure/enclosure at 1385 (‘modern’ concrete roof):
OK, we now have Pashley following a kalderimi which gets him south of the depression down to Timos Stavros. He says that he traversed the mountain on a very poor ‘road’ (i.e., trail).
So, Pashley’s route probably followed, more or less, the current location of the road down to the Anopoli plateau. It is usual for routes that are not over steep rocky sections to be nothing more than footpaths (e.g., some of the high mountain routes, as an example; or other routes through mid-level forest). Even if not covered up by the modern road, such route locations deteriorate rapidly and no longer exist in a usable condition.