Madeira and Porto Santo
A volcanic island where the weather changes with the altitude, and a sister island that is one long beach.
Madeira is vertical.
The island rises to 1,862 metres at Pico Ruivo in under twenty kilometres from the sea, so cloud, sun and rain are usually all present at once in different places. The south coast is warm and dry, the north is green and wet, and the central peaks sit above the cloud line more often than not. Planning here is really about choosing altitude.
Levadas are the island's road network for water.
Hundreds of kilometres of irrigation channels were cut across the cliffs from the fifteenth century to carry water from the wet north to the terraces of the south. The maintenance paths beside them are now the walking network — mostly level, sometimes vertiginous. Levada do Caldeirão Verde and the Rabaçal paths run through Laurisilva, a UNESCO-listed laurel forest that predates the last ice age.
Funchal, and what is actually good in it.
The Mercado dos Lavradores for fruit and scabbardfish, the Zona Velha for painted doors and dinner, and the Monte cable car with the wicker toboggan ride back down, which is a genuine nineteenth-century transport survival rather than a theme-park invention. Madeira wine lodges in the centre pour thirty-, forty- and hundred-year-old bottles by the glass.
Porto Santo is the opposite island.
Forty minutes by plane or a two-and-a-half-hour ferry, and nine kilometres of flat golden sand with almost nothing behind it. It is dry, low and quiet, and locals go for the sand itself, which has a long-standing therapeutic reputation. One day is enough to see it; three is better if the point is to stop.
When and how.
Madeira works all year — winter averages sit in the high teens. Whale and dolphin boats run most months. Roads are steep, narrow and heavily tunnelled, which is the main reason visitors take a driver rather than a rental car.