First timer 3 weeks trip itinerary to Japan

Hi everyone,

We are a couple in our early 30s and would like to double check our first-time [refined] itinerary for Japan. We have the idea to go in early May 2026, making sure that we arrive in Japan at least a few days after the Golden Week ends (to avoid the crowds and for the weather).
I have asked for help before in this sub but now we are about to book the trip and so I want a sanity check, just to be sure we are not missing anything. Would be happy to know about any tips and recommendations as well.

Our background & goals:

Despite all temptations, the endless spots to see and the FOMO, we want a relaxed and doable itinerary. So in some places we want to take our time and take it easy and avoid rushing in & out of crowded touristy spots. We will rely on public transport (trains and maybe buses). We want to do Shimanami Kaido over two days. We are also foody and love to try the local cuisine. We are not so much into nightlife anymore but do not mind to visit some Sake/Whiskey breweries & some nice izakayas. We would like to fit in a few easy hikes for the nice views, not so far from the cities below. Though it is tempting, but we decided to skip Osaka for this trip or will just keep it as a day trip from Kyoto. We do not want this trip to be very expensive and would like to keep within the budget.

Questions:
1. We are considering day trips from Kyoto to Nara & Uji. I would like to know if there is any other place that worth the day trip from Kyoto (other than Osaka) just in case since we have 5 days in Kyoto.
2. Regarding Kobe, is it worth staying there for two nights or do you think Himeji is better? Or if there is a 3rd option, I would like to know about it.
3. Does it make sense to allow 2 nights in Takamatsu? Enough to see & do?
4. Likewise about Matsuyama, is 2 nights too much or too little? Since we may arrive there a bit tired right after our Shimanami Kaido bike trip.
5. Also I want to know if Imabari is worth the visit? Shall we swap Matsuyama for Imabari or never mind?

For now here is the idea for 21 nights in Japan:

–> Arrival to the Osaka airporrt after a long flight & take the train directly to Kyoto.

  • Kyoto (x5 nights)
    • Visit Fushimi Inari Taisha shrine
    • Visit Kinkaku-ji
    • Arranging a Kaiseki multi course meal
    • Matcha cafes in Uji
    • Maybe a Japanese Whiskey brewery visit
    • Day trip to Nara & sights there
    • Sake bars in Nara & trying Kakinoha-zushi
    • We will avoid Arashiyama bamboo forest as we heard it has become over touristy

–> Take train to Kobe (~1hr)

  • Kobe (x2 nights)
    • Try Kobe beef
    • Hiking to Nubobiki falls
    • Visit Sake breweries in Kobe
    • Leave Kobe early in the morning to stop by Himeji to visit its impressive castle

–> Train from Kobe to Himeji & then after the castle visit, take train to Onomichi

  • Onomichi (x3 nights)
    • Take it easy & relax
    • Try local Onomichi Ramen
    • Explore the town & the cat paths & a small hike for the views
    • Prepare for Shimanami Kaido bike trip

–> Pick up bikes and start Shamanami Kaido

  • Overnight stay in an island (maybe Omishima) (x1 night)

–> Continue the bike route to Imabari & hand over bikes. Then take the train to Matsuyama

  • Matsuyama (x2 nights)
    • Visit Dogo Onsen (either the tour or use the baths)
    • Visit Matsuyama castle
    • Try the Matsuyama oranges

–> Take train from Matsuyama to Takamatsu (~3hrs)

  • Takamatsu (x2 nights)
    • Visit Ritsurin Japanese garden
    • Maybe hike Mt. Yashima & enjoy the view
    • Try local Udon noodles

–> Take train from Takamatsu to Tokyo

  • Tokyo (x6 nights)
    • Take it easy & relax
    • Visit Izakayas
    • Maybe a Karaoke night
    • Maybe visit a skyline view point
    • Shopping
    • Etc.
    • Pack bags:(

–> Flying back home..

Many Thanks in advance! 🙂

by Whole_Remove8338