Does this timeline make sense for my first Japan trip?

Going to Japan for the first time, flying into Osaka, KIX on August 4 and departing from there August 24. I’m planning on staying a while in Osaka maybe August 4-14, I’ll do day trips to Nara / Kyoto and anywhere else people suggest! Going with my boyfriend and this will be his third time so trusting him to show me some spots.

Then we’ll go to Tokyo maybe 14-18. I read about it being Obon that week and travelers will be coming and going from the train so it might be busier. Any suggestions would be great in terms of dates as i haven’t booked any accommodations yet. Then planning on Hakone for 18-20 for onsen time and back to Osaka from 20-24.

I will take any advice, tips, and recommendations to better prepare. I know there’s much more worth seeing there so I already know I’m going back to experience Okinawa one day.

by mushroomind