2 week itinerary help

The JRP does not cover the Tateyama Kurobe route and neither the bus to Shirakawago. I don't think you would get value out of the rail pass with this itinerary. One of the Tobu Nikko Passes could make sense though.

Are you arriving on day 1 or on day 0?

We have 15 full days at the start of May.

Are you aware of Golden Week and all the problems it causes?

Generally I recommend to travel between cities in the early evening, not morning, because it gives you more effective sightseeing time. (e.g. day 6, etc)

A few comments based on my interests (which might be very different to yours):

Matsumoto has some good sights, but is IMO a bit boring for an overnight. If possible I'd visit it on the way to somewhere, though I realize that is not easy in your case since you have the Alpine route after it (which does require lots of time).

Half a day is very little time for a nice place like Kanazawa.

Only 1.5 days in Kyoto. Just for the highlights I'd give Kyoto at least 3 full days. Temples, shrines, gardens, traditional houses, crafts, and it is just a very pleasant place to walk around in.

Unless you have anything special to do in Osaka (that you cannot do in Tokyo), I'd skip it. Getting to the airport from Kyoto is not difficult. Could also think of going to Osaka for an evening only from Kyoto (after temples close around 5pm).

Not too thrilled about going to Okinawa for two days either, but if that's what you want.... In any case I would not spend those days in Naha, which would be just another big city.

Nikko is much better as an overnight, though I realize you don't have time for that.

Thank you, this is really useful.

We have 15 FULL days - we arrive on day 0, and we fly on day 16.

I agree it doesn't look like there is that much in Matsumoto - was only thinking of staying there to get onto the Alpine route early morning. Do you have any other suggestions of how to better achieve this?

Kanazawa - it is only half a day, but we spend 2 nights there - I thought we may still be able to experience it if we were there for 2 evenings as well as half a day?

Kyoto similarly - was thinking we would have evening time to experience the city, but your point on Osaka is interesting - maybe we will skip it in favour of more time in Kyoto. I had read nightlife is good in Osaka so was planning on going out there, but I imagine we can do that in Tokyo and it will be similar (and probably Kyoto too)

Okinawa - we essentially want to spend a couple of days somewhere more 'beachy' and Okinawa looks picturesque, so we thought it would be a good option. Are there better options if we're looking to relax for a couple of days by the coast?

Thanks!

Sorry, further point on the golden week...

We are aware of it, and aware that tourist spots will become very busy, but could maybe use more guidance here... where I say 'day 1', 'day 2' above, this correlates to 'may 1', 'may 2' etc.. I understand the busiest Golden Week days are 3 May and 5-6 May - where we are scheduled to be in Matsumoto, Shirawakago and Kanazawa... would these places be overly busy on these dates?

I'd agree with most of the comments by bamse above (apart from Matsumoto,which I think is an interesting city with quite a bit to offer,depending on your interests of course).

For me it is far too rushed.

There is absolutely no point flying to Naha when you could spend that time somewhere like Kyoto.It won't be beach weather anyway.

With 15 full days,I'd be looking at something like.....4-5 full days Tokyo.4-5 in Kyoto.5 days Matsumoto to Kanazawa.

I'd drop Osaka and Okinawa.And decide on day trips (Nara,Nikko,Hakone) when you are there...you may find you want to do them,or not.

re Matsumoto: By "boring" I only meant that I found it difficult to spend an evening (after 5pm when things close) in any meaningful way. You could hang out around the castle which is nice and lit up at night, but other than that, it did not feel like it had any nice area for a walk or something. Perhaps I was just in the wrong place!? I don't have any idea how to avoid spending the night there with your itinerary.

Experiencing Kanazawa and Kyoto in the evening is possible to some extent. Sights will be closed, but walking through the traditional neighborhoods is possible and visiting some of the (shinto) shrines as well. However there are so many interesting things to do during the day that it feels like a pity that you cut your time that short there, particularly seeing with what other places (Osaka, Naha...) you fill your time. Unless you have very little interest in traditional Japan, I'd highly recommend to make some more time for at least Kyoto.

I am not much of a nightlife guy so can't comment on whether it is fundamentally different to what you get in Tokyo. This whole Osaka being recommended for nightlife (and food) to me seems more like a plot by the local tourism agency in lack of other attractions. (I know, a bit too harsh and perhaps wrong. Also this comment is in view of you having limited time in Japan and having to prioritize.)

Are there better options if we're looking to relax for a couple of days by the coast?

Mainland beaches are not all that great. The closest decent beach to your itinerary is perhaps in Shirahama on Izu Peninsula. If you go to Okinawa make sure where you are going. Naha and the main island of Okinawa are not known for good beaches.

As an alternative you could consider an onsen for relaxing. Those are all over Japan.

would these places be overly busy on these dates?

Everywhere of tourist interest will be overly busy in Golden Week. Book your accommodation now!

I understand the busiest Golden Week days are 3 May and 5-6 May - where we are scheduled to be in Matsumoto, Shirawakago and Kanazawa... would these places be overly busy on these dates?
Considering Matsumoto has a famous castle and Kanazawa has one of the 3 top gardens in the country, I'd say yes. Bottom line is this: have you made hotel reservations for the GW period yet?

Everywhere touristy will be busy.And so all those places on your itinerary.....

I was in Matsumoto's castle during Golden Week a few years ago and it was indeed very crowded. Queuing to get up and down. But there is also a sense of ordening and discipline. So crowded yes, chaotic no.