The last proper road in the Mani runs out at a scatter of stone, a lighthouse and a lot of wind, and that is Cape Tainaron, the southernmost tip of mainland Greece. Ride south from Areopoli or Gytheio through the tower-house villages of the Deep Mani and the landscape gets steadily barer: limestone ridges, terraced walls with nothing growing on them, silver olive groves in the folds, and the Taygetos range standing behind you like a wall. The surface is mostly decent but narrow, and goats treat the tarmac as part of the pasture, so ride the blind bends as if one is waiting around each.
The old name matters here. Ancient Greeks believed a cave near Tainaron was an entrance to Hades, and Herakles was said to have dragged Cerberus out through it. There was a temple of Poseidon on the cape too, and in antiquity the place was a sanctuary and a landmark for sailors dreading the rounding of the peninsula. Today you walk the last stretch on a path rather than ride it, and you should, because the sea opens out to the horizon with nothing between you and Libya but water. Mani people were famous for their feuds, and the stone towers you pass all the way down were built partly for that, partly to keep the family's pride in the skyline.
Be sensible about supplies. Tavernas in the nearby villages tend to open on a seasonal rhythm, so a late lunch is safer than an early one, and anything you find will be simple: grilled fish, lemon-heavy salads, local sausage with orange peel.
Come in spring or October if you can. In April the slopes are green and dotted with poppies, and the light over the water is soft; in August the heat and the glare are punishing in leathers. Late afternoon is best of all, when the stone turns gold and the ride back north has the sun behind you. It is a dead end, so you will ride the same road twice, but the second time the view over your shoulder is the better one.