20 days in Japan, places to prioritize

We are so excited to be spending 20 days in Japan mid-June 2024 and are trying to plan our trip to maximize the experience. Arriving at Haneda we plan to spend a few days in Tokyo before travelling south-ish. We are more interested in maximizing the experience of what we do and visit, rather than tick as many boxes as possible. We are travelling with our two teenagers (one of each) so interest include shopping, gaming, sneakers, ninjas, food, culture and performance cars :)

Current itinerary;
Day 1-3 Tokyo (including visit to Yokohama etc)
Day 4-6 country side (on our way south/west to Osaka)
Day 7-11 Osaka (visiting Kyoto, Kobe and Nara etc)
Day 11-14 not decided (flying to Okinawa on day 14)
Day 15-17 Okinawa beach life (flying to Tokyo on day 17)
Day 18-20 Tokyo shopping and eating (flying home late on day 20)

Any tips and feedback is highly appreciated.

Arigato Gozaimasu!

If you and your teenagers are interested in the ninja tradition, have you ever checked the link below on this website?
https://www.japan-guide.com/e/e2295.html

I haven't personally visited any of these places, so I can't provide you with direct and realistic comments. However, some of them may align with your itinerary, especially considering their locations in the countryside on your way south/west to Osaka.

Per your profile you are from Sweden. How good are you and your kids with humid heat? June CAN be still okay but it can become unbearably hot and humid. So my advice would be to not pack too much in each day. Leave some �gnice to have but not mandatory �gdestinations in each day. Eg only half a day worth of actually planned activities and the rest as bonus if the family is feeling it

I would add few more days in Osaka/Kyoto/Nara - especially Kyoto.
You can do so during Days 4-6 and 11-14.

Suggestion for Day 4&5: Hakone, https://www.japan-guide.com/e/e5200.html

Suggestions for Day 12-14:
Himeji, https://www.japan-guide.com/e/e3500.html
Kurashiki, https://www.japan-guide.com/e/e5750.html
Hiroshima, https://www.japan-guide.com/e/e2160.html

Kyoto and Tokyo need more time. Do worry about adding more places you aren't initially interested in.

I agree with LikeBike. June can be extremely hot, Kyoto in particular is like Satan's rectum, although if it is drizzly if can be quite pleasant. Tokyo and Osaka also get super hot, though Kyoto is next level due to its topography.

I would try to limit city time and get to some higher or breezy areas, eg swap some Kyoto time for Nara, Kamakura and Enoshima. I would also look at Karuizawa (mountain resort town with great shopping that I have been told I over recommend), Matsumoto, Kamikochi, Takayama (Takayama gets plenty hot as well, but you can essentially go easily between those 4 areas by bus and train, so I would include it).

You will travel in the rainy season in Okinawa, this article may be interesting (translation by google).

https://00m.in/7ysux

While the first part of June is not too bad, from around mid-June the rainy season starts, and you can get hit with several days of pouring rain, so keep that in mind and have a back up plan (e.g. museums and aquariums). Even worse is the sweaty humidity, plus day after day of heavy overcast skies - rain, or about to rain. On the plus side, the hydrangea are gorgeous, and you should definitely see some places famous for them, like in Kamakura. It's also iris season, and you will see some immense beauty there too like the Horikiri Shobuen Iris Garden and Meiji Shrine garden in Tokyo.
In any case, if you want to see some other places, Days 4-6 you could visit some nice places outside the big cities, like Nagano and Kanazawa, taking the Hokuriku route down to Kansai. Places like Karuizawa and in the higher elevations of Nagano can give you some relief from the heat and humidity. Foe what to do after the Kansai cities, you have several options. You can stay in Kansai and do some nice day trips like Amanohashidate, Miyama, Otsu, etc, or do an overnight at Koyasan which is quite a different experience. Or take a trip down to Oakayama, Takamatsu, or Hiroshima. An overnight at Hiroshima is preferable though, with a day for the city and one for Miyajima (and maybe even fitting in Iwakuni).
Okinawa has several great places to see, though renting a car is the ideal way to get around. It takes about 2 hours to get from one end of the main island to the other. You can get some good cheap tourist airfare's like JAL's Explorer Fare for about 11,000 per flight one way.

You have been given great advice. Since you only have a short time in Tokyo, you can skip Yokohama. Also, stay in Kyoto and do a day trip to Osaka, or just skip the latter.

The Japan Explorer airfare is very worthwhile--not only is the fare reasonable, it also allows two check-in bags per person.