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Nakasendo way. From Hakone and then to Kyoto

Hi! I’m looking at checking out the Nakasendo way at the end of November. I have 5 nights set aside after leaving hakone and arriving in kyoto.

Is it possible/enough time to make the most of this part of Japan? Ive just started figuring out logistics of my itinerary with the trains/buses so still feeling slightly overwhelmed by all the information. I’m just wondering if travelling from hakone to magome/tsumago and surrounding area and then out to kyoto isn’t going to be a headache of a route?

Any help or reassurance would be greatly appreciated! Really keen to experience this part of Japan.