We spent a bit over a week in Tokyo, Kyoto and Osaka. We only stayed in Tokyo and Kyoto (Osaka was a day trip). I’ve heard that Osaka can be more interesting than Kyoto but we had more places in Kyoto that we were interested in seeing. The Japan Rail pass is a must have if you are thinking of taking the train between Tokyo and Kyoto or Tokyo and Osaka. (This must be ordered in advance – more info here https://www.japan-guide.com/e/e2361.html)
I’ve included a rough overview of where we stayed and what we did each day – we’re not super intense when we travel so tend to take our time! I know people who did a lot more than we did in a shorter time. I can look back at specific photos/notes if you’re curious about anything below.
Day 1:
  • Arrive in Tokyo from Taipei
  • Pick up Japan Rail Pass (order this in advance as there’s a letter that has to be shipped to a non-Japanese address)
  • Stay in Airbnb in Ebisu area
Day 2:
  • Explore Shinjuku area (Isetan is a large department store, Don Quijote is a famous chain discount store, Piss Alley is a street with lots of food stalls)
  • Eat at Matsuya (local chain restaurant)
Day 3:
  • Explore Akihabara area (lots of small electronics stores)
  • Meiji Shrine
  • Shibuya Scramble (this is best viewed from the Starbucks on the north end of the crossing – you can snag a nice window seat and watch the craziness from above; the Starbucks is inside a book store)
Day 4:
  • Tsujiki Market (I think this market closed recently but I may be mistaken; they used to have fresh fish for breakfast if you go early)
  • Lunch at Nakajima (Michelin star rated Japanese restaurant, very affordable for lunch, but you have to line up outside in advance)
Day 5:
  • Took Hikari train from Tokyo to Kyoto using Japan Rail pass
  • Stay in ryokan in Kyoto (Motonago was the name) – traditional guest house with tatami beds
  • They served us dinner in our room
Day 6:
  • Breakfast served in ryokan as well
  • Explore historic Kyoto area
  • Visit Fusihimi Inari Taisha (shrines)
  • Stay in downtown Kyoto at modern hotel (Hearton Hotel)
Day 7:
  • Day trip to Osaka + Himeji using rail pass
  • Himeji Castle was beautiful but required a lot of climbing
  • Osaka has a very popular ferris wheel at the top of a department store downtown
Day 8:
  • Arashiyama Monkey Park
  • Train Museum
Day 9:
  • Hikari train back to Tokyo
  • Stop at Daimaru (store in train station) for souvenir desserts – e.g., Tokyo Bananas and baumkuchen (thousand layer cakes)
  • Train to airport for flight home