First Time Itinerary (10/5 to 10/26)

Going for the first time in October. Here is my proposed itinerary with overnight locations listed, daytrips, rest days and geographic areas I tend to explore that day.

Saturday, October 5th – Departure
Sunday, October 6th – Arrival
Monday, October 7th – Tokyo (Shibuya)
Tuesday, October 8th – Tokyo (Shinjuku)
Wednesday, October 9th – Kyoto (Gion Area)
Thursday, October 10th – Kyoto (Northern Kyoto/Laundry)
Friday, October 11th – Kyoto (Arashiyama)
Saturday, October 12th – Kyoto (Eastern Kyoto & Fushima Inari)
Sunday, October 13th – Nara
Monday, October 14th – Hiroshima
Tuesday, October 15th – Miyajima
Wednesday, October 16th – Osaka (Minami/Laundry)
Thursday, October 17th – Osaka (Bay Area/Kita)
Friday, October 18th – Hakone
Saturday, October 19th – Hakone/ Lake Kawaguchiko
Sunday, October 20th – Lake Kawaguchiko/Tokyo
Monday, October 21st – Daytrip to Nikko
Tuesday, October 22nd – Tokyo (Laundry
Wednesday, October 23rd – Tokyo (Akibahara)
Thursday, October 24th – Tokyo (Asakusa)
Friday, October 25th – Tokyo (Odaiba)
Saturday, October 26th – Departure

It looks fine, albeit you might struggle to find enough to do in specific areas of Osaka and specifically Tokyo. I'd also suggest staying the night or two in Nikko to give you a real taste, including upper Nikko which has great walks in nature if that's your thing.

Also note we don't really know what you want us to do with your post. Do you want feedback, ideas???