Kalamata is the doorway to the Mani, and the olive capital of Greece, as the dark purple Kalamata olive is known the world over. Groves of olive trees fill the plain of Messenia, and the city sits at the head of the gulf with the great wall of the Taygetos range rising behind it, its summit at Profitis Ilias well over two thousand metres, often capped with snow into spring. The city is a lively mix of seafront, markets and a pedestrian old town, and was rebuilt after a damaging earthquake in 1986.
It also has a place in the national story. On 23 March 1821, Kalamata was the first major town to be liberated in the Greek War of Independence, and local people celebrate the anniversary. The ruined castle on the hill above the old town, with its Frankish and Venetian walls, looks over the plain.
The route south enters the Mani, the central of the three peninsulas of the Peloponnese, a stern, rocky land of stone tower houses, bare hills and tiny villages. The road follows the coast, then climbs through hairpins into the interior. The surface is mostly good, and the traffic is light outside the summer weekends. The Taygetos road to Sparta, the Langada pass, is one of the great mountain roads of Greece, cutting through pine and plane forest, with a descent of many hairpins. Be careful with gravel and with goats on the road, and in winter, check for ice and snow.
Kalamata has over fifty thousand people and all the fuel, food and supplies you could want. Farther south, villages are small, so fill up before you leave. The olive oil is outstanding, and the local figs, honey and pasta are worth carrying away. Order a plate of lamb and potatoes in a taverna, with a village salad and a glass of cold white wine, and enjoy the sea breeze. Ride early in summer, because the sun by midday is strong, and give yourself time at the southern tip, the ancient Cape Tainaron, where the road ends and the sea begins.