Funchal at Night
Levada dos Piornais
Levadas are water channels which run from high up in the rainy mountains to the dry southern valleys of the island. To allow maintenance, these channels usually have a side which is wide enough to walk on it. It turned out they could be used for hiking as well and are now (partially) being equipped with rails because they often run along serious drops. Levada dos Piornais is good for trying out if this kind of hike is for you. It starts right in the city of Funchal, where its all nice and flat. It starts having drops which are getting higher and higher. At first there is a rail, later there isn't. The trip ends at a locked iron gate which indicates that things are going to get worse beyond.
Pico Do Arieiro to Pico Ruivo
Hike from second highest to highest mountain and back. With 30km diameter, Madeira is rather small, but its highest mountain reaches up 1860m. The result being steep ascends and descends. The round trip distance between the two mountains is only 12km, but the change in elevation is 1km up and down. Virtually all of it is accomplished using stairs. This compares to climbing 300 floors. And no, I did not count the steps.