Travel around Magome and Tsumago in January

We are a group of 7 travelling to Japan to ski in January. We were hoping to travel from Tokyo to Nakatsugawa (staying one night) then walk from Magome to Tsumago, then train to Matsumoto (staying one night) and then on to Nozawa Onsen.
Can you advise if this is worth doing, we have booked our accommodation but it can be changed. Also I read somewhere that luggage is not transported at this time of year - so what are the alternatives?

Not recommended. It will be very cold, likely frozen and snowy, with very few people on the trails. You could always travel between the two by public transportation rather than hiking. But you're right, the luggage service does not operate during the winter.

It may be doable if the weather is good, but I would not count on that. Here is a post from the tsumago tourism board recommending against winter hiking on the nakasendo.

http://tumago.jp/blog/post-803.html

Thankyou. Would you recommend visiting this area at all then in the winter? We could just visit the towns of Magome and Tsumago but not walk??

You could still go. But expect many of the touristy shops and restaurants to be closed as they don't expect visitors.