Ten day itinerary for May/June?

Hi all! I am taking a first time trip to Japan in late May and need itinerary advice for a 10 day solo trip. After that, I join family for a group tour of Tokyo, Osaka, Hiroshima, etc. Some of my ideas are a couple days in Tokyo to get acclimated. Get a two week JR pass, take a longer train trip (to Hokkaido?) to see more country by train and during my trip, focus on destinations served by JR. Generally avoid the bigger cities, except for Kanazawa (which is a must see for me for the garden and pottery). Explore the Japanese Alps and do some day hikes. I want to experience castles, shrines, great scenery, art, culture, ryokan, a capsule hotel, and perhaps a temple stay. I have spent many hours researching Japan have a few routes in mind, but I would really like some input from travelers with Japan experience. Thanks!

Many places can be reached by JR, but please make sure before you get the pass that the pass pays off for your itinerary. You say you are going for the 14-day one – will you be able to use your pass when you join the family, or is that an arranged tour that you don�ft pay individually for the transportation?
Difficult to make suggestions without knowing exactly where you�fd go with the tour and where you�fd be joining the family?

Hi, 10 days coming in and out of Tokyo?

I would go:

Tokyo - Matsumoto (castle town) overnight - Takayama (by bus via Kamikochi worth a quick stop or overnight at Onsen Hotel) 2 nights - bus to Kanazawa stopping 2 hours at Shirakawa-go, Kanazawa 2 nights - train (Thunderbird) to Hikone (near Miabara, nice castle town) overnight. Then decide whether to continue to Kyoto or preferably Nara (overnight) back to Tokyo. Ryokans are at pretty much every place, though I would probably look for one at Takayama or Hikone.

Thanks for the responses. I really appreciate it. Our tour begins near Kyoto and it includes Nara. But I will take a closer look at Hikone as a possible overnight, and then go to Kyoto the next day to meet up with the family.
Do you guys have any other suggestions for a fun or scenic train ride on the Shinkansen other than from Tokyo to Hokkaido?

Tokyo to Hokkaido on the shinkansen, scenic? I think not. Shinkansen aren't scenic, especially on the Sanyo. Tohoku isn't much better. Maybe Tokaido with Fuji and around Hamamatsu, but that's it.

If you are interested in touring your way up to Hokkaido, there are lots of great sights to see along the way. For example, Geibikei is just stunning in its beauty and wonderful to see all the koi fish swimming wild in the river and not just captive in a pond.
https://youtu.be/NNsGoa4wWOo

Hirosaki is also very beautiful and the Fujita Garden is one of the most beautiful in the region.
https://youtu.be/tfyYJV1LTjc

Plus lots of other as well, like Sendai, Matsushima, Yamadera, Hiraizumi, and others. But if you just want to get up to Sapporo, then flying will save you several hours and from a lot of boredom. The window scenery is better than the Sanyo line easily (which has lots of tunnels), but if you really want to be in Hokkaido, then spending more time there is a much better solution for you.
Also consider where you are going and for how long. You get very little, if any, value from a rail pass by staying put in some city. It is made for long distance travel - but given that you can fly there for 11,000 yen by ANA's Experience Japan Fare or even less on a low cost carrier like Jet Star or Peach, both money and time need to be considered. It's up to you to decide where you really want to go, and then choose the best way to get there.

Since you'll be doing the Golden Route with your family and starting in Tokyo, I highly recommend doing a trip through Central Japan (Chubu) region. There is plenty to see and do in the course of a ten-day trip, and it would be chock-full of experiences on your bucket-list in Japan. It also moves in a westward direction, so it conveniently places you in Kyoto at the end so you can easily meet up with your family after that.

Tokyo (3days)> Nagano (3 days)> Kanazawa (2 days)> Kyoto (2 days)

Tokyo: Odaiba, Asakusa, Shinjuku,
Nagano: Zenkoji Temple, Lake Suwa, Matsumoto Castle, Alpine Route
Kanazawa: Kenrokuen Garden, Omicho Market, Higashi Chaya street, Shirakawago
Kyoto: Lake Biwa, Arashiyama, Gion

Also, if you do intend on exploring central Japan, I recommend instead of getting the 14 day Nation Wide Pass you opt for one of the central passes :

https://touristpass.jp/en/ or https://hokuriku-arch-pass.com/en/

as they can cover your area of travel for a fraction of the price. Enjoy your trip to Japan!

Thank you all very much for your responses. It has helped tremendously. My reason for going to Hokkaido was more for the journey of getting there rather than just the destination. I understand now why the shinkansen is not scenic, so Hokkaido is no longer on my list.

Thanks especially to afiqtravel for the itinerary recommendation. I think that is pretty much spot-on what will work for me. I will focus my research on the Chubu region. As an aside, I see they have an annual Hyakumangoku Matsuri festival in Kanazawa during the last weekend in May. That looks like a lot of fun and I should be able to adjust my schedule so I can attend.