Itasuke is a modest keyhole-shaped mound from the same age of burial monuments that gave the city its World Heritage listing. It sits amid ordinary streets, one more piece of green surrounded by tiled roofs, with its moat and trees telling you that something older than the neighbourhood is under there. It is a reason to arrive early, on a quiet weekday morning, and see what a city looks like before the engines warm up.
The reason to start here is the road that follows. Kumano Hongu Taisha lies far to the south in the mountains of Wakayama, one of the three grand shrines of the Kumano region and the spiritual heart of a pilgrimage network that people walked for a thousand years. Emperors and ordinary farmers made the trip. The original shrine stood on a sandbar at the meeting of rivers until a flood in 1889 swept most of it away, after which the buildings were moved to higher ground, and the vast steel torii gate that stands at the old site is the tallest of its kind in Japan. It is a good place to see how Shinto and Buddhism mixed here, with no sharp line between them.
Getting there is the real adventure. From the plain you climb through Nara and then Wakayama on routes that follow rivers and ridges for long stretches, often with a single lane in each direction, and the bends come one after another through cedar plantations and past little villages that are stacked up the hillsides. Landslides and heavy rain have damaged this area repeatedly, notably in the typhoon of 2011, so check the status of roads before you set out. The tarmac is often rough in the shadows, and moss and fallen branches are common.
Keep the tank topped up in Sakai or the first towns on the way, because south of the main valleys the stations are far apart and some close early in the evening. Convenience stores are the reliable source of coffee and food, and a bowl of noodles at a roadside restaurant tastes better than it has any right to. Plan a night in the Kumano area if you can: the hot springs at Yunomine are among the oldest in Japan, and a long soak after a day on the bike is exactly what the legs need.