Take freeway 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.
Altitude gain: 1200m
Trailhead: Boca da Encumeada
Probably the most beautiful but most strenuous tour. It affords quite a lot of different views towards virtually all parts of the island.
The trail starts directly at Boca da Encumeada and winds up and down along the weather divide until it reaches Boca das Torinhas. A little before Boca das Torinhas turn right and head directly towards Pico Grande. You'll have to descend some 300m and later reascent towards the castle-like eastern face of Pico Grande's summit block. From there descent slightly to the southern side and from there climb the final steps toward the summit.
Hiking gear and long pants (because of the gorse). Take into account that part of the hike is exposed.