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Japan without Reservations in May

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I arrive in Japan mid May 2014 for a two-week trip. I'll be staying the first night at a Narita hotel (after 13 hour flight), then I want to travel north, visiting a number of cities. I hope to make it all the way to Sapporo. I will have Japan rail pass. I would prefer to be somewhat spontaneous and do not have hotel reservations except for the first night. I'd like to just arrive in a city and walk around to look for hotels with vacancies.

Do you think this plan is wise or foolish? Would it be smarter to have the trip fully booked with hotel reservations?

Thank you for any suggestions!

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