Japan Itinerary Check (Oct 15–28) – Tokyo, Kyoto, Osaka day trip, Okinawa

Hello!! First time to Japan this October (couple, early 30s). Traveling from the US. Super into food, hiking/nature, big into anime and pop culture, also history and culture. We enjoy wandering, trying local food, and late-night vibes if the place is fun — but not into rushing from spot to spot just because our itinerary says so.

Plan so far:

  • Flying into Tokyo Oct 15 late evening.
  • Tokyo (Oct 16–19): Planning to stay in Shinjuku. Thinking Asakusa, Skytree walk, Meiji Jingu, teamLab Planets/Borderless, Shibuya Sky, and a day trip to Hakone.
  • Kyoto (Oct 19–23, planning staying in Gion/Kawaramachi): Arashiyama, Kinkakuji, Philosopher’s Path, Nishiki Market, Fushimi Inari. Day trip to Osaka included for Osaka Castle, Dotonbori, and evening/night spots in the city. Also want to check out the Jidai Matsuri festival on Oct 22.
  • Okinawa (Oct 23–26, Onna Village): Beaches, Churaumi Aquarium, Cape Manzamo, and some driving around.
  • Back to Tokyo (Oct 27–28) for last-minute shopping/sightseeing before flying home.

Transport: Tokyo → Kyoto by Shinkansen, flight from Osaka → Okinawa → Tokyo, rental car in Okinawa.

Questions:

  • Does this feel too tight or doable?
  • Anything we’re missing that’s a must-see/do/eat at?
  • Any tips for Hakone or Okinawa?

Thanks so much in advance — this community has been super helpful in getting our planning off the ground, really appreciate all the tips and insights here! 🙏

by citizenvein