Madeira is split in two by the road 104, running north to south between Sao Vicente and Ribeira Brava. If you are in a hurry, you can take the tunnel through the massive, but we definitely recommend the old road that runs along Encumeada. Encumeada lies at an altitude of about 1000 meters, on the ridge which separates north and south. You can see from there both the northern and the southern coast.
From Encumeada, you can reach the Pico Ruivo (1862 m). You walk along the Pico da Encumeada (1580 m), the Pico do Jorge (1691) and the Pico das Erinhas (1649 m). A walk of about 15 km, with a level difference of about 1000 meters.
Right from the start it is clear that this is going to be a tough hike; at times it goes up steep; the path is well defined but never secure. Moreover, a cold north wind is blowing over the ridge. We started this walk, but turned back halfway.
We recommend this tour only to experienced hikers. If you decide to go for this walk, be sure to take enough enough food and drinks with you.