This is the classic peaks of Madeira: Pico Ruivo and Pico Arieero, both easily accessed with car or taxi. Not as easy with bus. I wanted to do both of these mountains as an A – B tour with my full backpack so I could move from Funchal to São Vicente. I took the bus to Poiso and started walking towards the radar dome of Pico Arieero, but gout get a ride the the parking lot. I did these trails with all my luggage so I did no running for me. Both these trails consists of a lot of steps, up and down and a few tunnels. So the running is not very flowy or fast, and the steps can be slippery. Still doable of course and the scenery is amazing. If I did this again I would do a longer trail, maybe start in Poiso and go all the way to Sao Vicente. Sleep and eat there and then take the bus back the next morning. So you can run without a heavy pack.
This is just something you have to to if you go to Madeira. The streams in the mountains are probably drinkable (I had a Sawyer filter as backup) but I didn’t have to try that. I carried ~2 liters of water.