I started in Funchal, taking bus 113 to Caniçal. There I ran back along the shore and then followed a mountain trail up some small peaks and eventually I came to the tunnel where most people start the trail called Vereda do Larano. Flowing trail running through picturesque villages on a Levada in perfect weather. Arriving at the look out viewpoint Boca do Risco, after that the trail takes on a new shape. It’s still very flowy and runnable, but on some sections the trail in 1 meter wide and then a steep cliff. I walked those sections. When approaching Porto da Cruz evidence of trail running appears as there is a couple of marked and graded trails around Porto da Cruz. I took the bus back to Funchal.
If you want to do a longer run, continue from Porto da Cruz to Ribeiro Frio adding ~16km and from there take a bus.