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Level: VERY HARD. Need to train.
Distance: 1,100km
Time: 6 weeks to complete.
Many people 'cheat' by working in a few local bus and taxi trips, or by skipping some of the temples. It's completely flexible as to where you begin, although tradition dictates you finish at the temple you started at. The quickest way to get to the island is by train from Osaka to Takamatsu port, on the north east coast - the nearest temple from here is Yashima Temple on flat-topped Mount Yashima.
I've compiled a list of hiking trails for experienced and non-experienced hikers in the different regions of Japan. (75% of Japan is mountainous)