Ribeira Brava is a south-coast Madeira town that sits at the mouth of a deep valley and the foot of the old road across the island. A small bay of dark pebbles, a church with a handsome tiled tower, a seafront that locals actually use, and then the mountains rise straight behind. It has roughly six thousand people, so petrol, cash machines, bakeries and a decent lunch are all easy, which is exactly what a start point should offer.
Madeira's coast is steep volcanic rock cut by ravines, and this valley is one of the big ones. The old road climbs from sea level to the Encumeada Pass at about a thousand metres in a tight sequence of hairpins and shaded bends, past terraced banana plots, vines, and the little stone levada channels that carry water around the hillsides. The expressway tunnels have taken most of the traffic, which is a gift: the old route is quiet, narrow in places, occasionally scattered with rockfall after rain, and a wonderful bike road if you like riding up a mountain with the view slowly widening behind you.
The history is mostly sugar and wine. In the sixteenth century this coast made a fortune from sugar cane, and later the island's fortified wine became famous around the Atlantic world. Even now you will see cane being grown and the local honey-cane rum served in the bars. The island rises from the ocean without a shelf, so weather behaves strangely: you can leave in bright sun at the shore and meet cloud and drizzle on the plateau above, then drop out of it again on the far side. Pack a thin waterproof whatever the forecast says.
Past Encumeada the ride opens onto the Paul da Serra, a high moorland plateau at about fourteen hundred metres, treeless and windy, with grazing cattle and a long straight road that feels like another country. Fuel is not available up there, so fill in Ribeira Brava or nearby Ponta do Sol before you start. Try a bolo do caco, the flat bread cooked on a stone, hot with garlic butter, and a poncha, the local lemon and spirit mix, but save that second one until the bike is parked for the day.