Japan in June

I just returned from Japan. It's a wonderful and relaxing trip.

I think you don't need to visit Osaka at all. It's a fun city but lacks historical monuments.

Nara: see if you have the extra time and energy to visit when you are on the ground. You will need to first recover from jet lag.

I used Google Fi for data. It's super convenient.

Not sure about Japan Rail Pass because I did not get one. The folks at tripadvisor.com can point you to the right direction.

Let me know if you have further questions.

I've been to all the places you mention.

For your time period, skip Osaka and go to Nara if you can fit it in. If you feel there is more to see in Kyoto, then stay in Kyoto.

I can't help with the railpass as i didnt get one.

I used my cellphone with Tmobile. It wasn't the fastest data but you can get a local sim card if you want it faster.

As for food, you won't have a problem. Restaurants are usually small and specialize. Inside the Kyoto train station there are three shopping areas with probably 50 different restaurants. One area had five ramen restaurants next to each other all specializing in a different type of ramen. Dont think of these as cheap little restaurants. They are all good.

One last thing.....bring some cash. Credit cards are not always accepted.

If you are not familiar with some of the "unwritten" rules in Japan, this video might help.

https://youtu.be/TtuGBtDEefQ

Thank you @Barkinpark and @Frank11
We will play Nara by ear depending on our jet lag and drop Osaka
The video was helpful for our prep

I did splurge on three nights at three different onsen ryokans and had once-in-a-lifetime experiences. I encourage you to do the same for Hakone.

Also, JR rail pass prices are set to increase later in the year. Get yours soon if you need them.

Here's my one big takeaway: there are lockers in train stations, very very helpful if you need to stash luggage. However. If you use one, pull up your map app and put a pin in your exact location. Look around, take a few reference photos of exactly where you are in the station. If you forget which of many, many banks of lockers scattered throughout the station you put your things in, you might have to switch your train ticket TWICE to have enough time to find your things. There was me, wandering through Kyoto station, holding up the receipt from the lockers, asking total strangers "Sumimasen, dokodesu ka?" Finally someone was able to point me in the right direction.

Dining recs- Buy Yukari Sakamoto’s
“ FoodSakiTokyo” which is an instruction to Japan’s foods. It also has many restaurants listed in Tokyo and Kyoto.. It is not a new book so check carefully with restaurant listings. We took a fabulous food tour with Yukari which was amazing! yukari.shinji.sakamoto@gmail.com
http://www.foodsaketokyo.com/
I am looking for the notes on where we enjoyed dining. We did two Kaiseki dinners, highly recommend that you have at least one.$$$ And also a favorite was a tempura restaurant, small, and there is no grease showing on the paper it is placed on when served. Tenmatsu.com is the one in the book that we enjoyed.
The restaurants tend to specialize in one type of food like yakitori, tempura or teppan. Lots of ramen and udon places for good inexpensive meals. We had some of the best food we have ever eaten!
I will add more when I find my notes on Japan, our meals.
Department stores have excellent casual restaurants in their basement levels. Really good. You can take your food to eat outside on their rooftops if available.

Food in Japan was amazing. Also, you don't have to confine yourself to Japanese food--their Italian and French restaurants are excellent. Ditto for their delicious pastries.