Take highway R101 until its end at Ribeira Brava. After the long last tunnel don't turn to Ribeira Brava but to Serra de Água (ER104). Just at the entry of the village turn left and go up to the pass. Park your car on top.
Altitude gain: 1000m
Trailhead: Boca da Encumeada (1007m)
This is a beautiful, but very long route. It follows the central east-west ridge of Madeira, often switches the sides of the ridge and climbs up and down a lot. Only do this rout when the weather is fine - you don't want to get caught in trade wind mist.
Start out from Boca da Encumeada heading directly upwards to Pico da Encumeada. The trail always is clearly visible and rather easy to hike though it sometimes descends very steeply into the shoulders between the summits on the ridge. It offers perfect views of Pico Grande and the central summits.
Hiking gear and lots of stamina.