Your suggestion for my Itinerary

Hi!
I have decided at the spur of the moment to travel to Japan 21-
29 May. Never been to Japan and have never much wanted to until just recently.
So don't really know much about this country except for their ''sakura'' from the pictures hence I am right now frantically trying to decide where to go.
Here is my plan. Let me know what you think.

21-23 May-Tokyo
23-27 May-Kyoto
Planning will be based in Kyoto and to go to Hiroshima, Osaka, Nara for day trips. Do you think day trip is good or should I do an overnight in Hiroshima?
27 May-back to Tokyo then head off to either Nagano or Matsumoto
Which town is a better place for just an overnight trip? Nagano or Matsumoto?
28- head back into Tokyo.
Departing 29 May

I am planning to get the 7-day JR rail pass. For my 2-3 days stay in Tokyo what tryo of train pass would you suggest that I get?

Your suggestions will be much much appreciated.

Regards,
TravelJapan

First off, it is really not possibly to say which pass, if any, would be best to use in Tokyo. It depend on where you are staying and where you plan to go. One thing is to get the NEX + Suica, to get from Narita to Tokyo. Details at the bottom of this page:

http://www.japan-guide.com/e/e2359_002.html

I would vote for Matsumoto, but don't go Kyoto, Tokyo, Matsumoto. Go from Kyoto (or Osaka, see below) directly to Matsumoto, there is a direct Limited Express at 09.25, arriving 13.03. Or 08.56 Hikari shinkansen to Nagoya, then the Limited Express Shinano at 10.00, arriving 12.03.

Personally, I wouldn't do an overnight in Hiroshima, but I would consider a couple of nights in Osaka against spending all your time in Kyoto.

Matsumoto castle is probably the 2nd(or 3rd) best preserved surviving castle in Japan and of course worth a visit, but then why do you miss Himeji castle? Is there any reason?

http://www.japan-guide.com/e/e2400.html

I know people would have quite different opinions - I would suggest making day trips from Kyoto to Osaka, Himeji, Nara, and Hiroshima (if time allows - there are plenty to see in Kyoto), and dropping Matsumoto/Nagano altogether unless you have some special interest there (You will be spending quite some time on trains if you go by your suggestion).

There is an itinerary suggestion function on this travel guide page - enter the number of nights you are staying in Japan, and they give you a reasonable suggestion.
http://www.japan-guide.com/e/e2400_tokyo_7.html

You mentioned that you're interested in sakura at the moment. I just wanted to let you know that the sakura season has already ended this year, so if that's one of your primary drives for coming, you might consider trying to plan for next year.

That said, there are lots of beautiful things to see in Japan besides sakura. If you specify some of your interests (technology, natural beauty, mountains, old architecture, temples, etc.) the forum might be able to help out and give a more specific itinerary suggestion :)

Thanks so much for all your suggestions. I am very keen to see the nature scene, experience the old nostalgic Japan feel, tea ceremonies, stay in traditional ryokan... Hope you get what I am interested in.Your suggestions please...

Out of curiosity, is it possible to visit Himeji and Osaka, even Kobe, in the same day while based in Kyoto? Himeji would be to visit the castle, but for Osaka it would probably be just to hang around the station and find some takoyaki.

I would suggest that you check out the japan rail website Hyperdia-

http://www.japanrail.com/JR_hyperdia.html

This site allows you to type in starting points and destinations , it then gives you many options of times needed and the cost.You can then decide how long it will take to travel from place to place and whether it is more economical to get a Jr pass or buy tickets as you go. The travel time varies greatly according to which train you choose and even the time of day and the number of transfers required. Also be aware that the fastest shinkansen -nozomi- is not covered by the JR pass but other shinkansen are. Good Luck!