Walking the Nakasendo Way

Hi, I am looking at going to Japan next May and was wondering if it is best to book a self-guided itinerary for the Nakasendo Way (3 days) or can you do it yourself and book along the way?
Any recommendations for other walks in Japan that are good to do for around 3 days?
And finally recommendations for nice places to stay in Kyoto for a special birthday :) thinking ryokan/onsen type.
Thanks in advance.

Hi Jude. Short answer is Yes, it's possible to do it yourself, but the real question is are you prepared to put in the time and effort to research and organise it yourself? What is "best" will depend on this as well as your experience, map-reading skills, language skills, etc.

I'm sure that there was a group staying at Tsuruya Ryokan at Karuizawa when we were last there, and they were walking the entire route. Personally I'd get the map of it and then pick some good bits and train between them where possible. If I was going in May, I'd start at Karuizawa and then go on to Bessho Onsen. May is a great time at Karuizawa and Bessho Onsen will often still have sakura well into May.

Then I'd go on to Nagoya and back to Narai/Tsumago/Magome. Then I'd go from there to Hikone. I'm not sure where the trail is at Hikone but it is there somewhere and it is an awesome town with a nice original castle.

I cant help you with a ryokan in Kyoto - we make pretty much our sole exception there and stay at the Hyatt Regency which is very nice - but for a real birthday treat I'd recommend a night at Nara Hotel Nara, in the old wing.