The Monte Toboggan is Madeira at its most improbable: visitors sit in a wicker sled while white-clad carreiros steer and brake it down steep streets from Monte toward Funchal. It began as practical transport in the 19th century and somehow survived as one of the island's great tourist rituals.
It is brief, expensive for the time involved, and undeniably fun. Pair it with the cable car up to Monte and the tropical gardens nearby, then treat the sled ride as a piece of living Madeiran eccentricity rather than a normal mode of transport.