Since Koya is close to both Osaka and Wakayama, you can start out from either city, or even closer to Koya if you prefer; in terms of transit access, it would be quickest to start out from Tennoji in south Osaka and just head due south (you have many roads to choose from). This option has the added advantage of being able to stop at, or rather go through, rural Kawachi-Nagano. You should be able to stop at a couple of places here and get a feel for the area and still make it to Koya with plenty of time before dark. If you don't have much time for this leg or want to reduce the mileage on the first day, leaving from Wakayama might be a better idea; it's a straight ride east along the river to Hashimoto where you turn right and start up the mountain. Quicker still would be to start from Hashimoto itself (it's a train stop). From Koya, this route goes straight south along the Koya Skyline (maximum elevation 1372m) and down through Ryujin (of hot springs fame), followed by a long, long downhill to a turnoff where you can either go east to Totsukawa in Nara Prefecture (45.5 km along a very twisty road - allow plenty of time) or southwest straight to Tanabe on the coast, which just happens to be an express train stop. Allow three days, with the middle one devoted to exploring Koya-san; there's a lot to see. Consider ending your trip with a visit to Shirahama, right next to Tanabe - it's probably the most popular beach resort in southern Kansai, and the word on everybody's lips during Kansai's hot, muggy summer.
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