First time in Japan (14 days) — Tokyo / Kyoto / Osaka itinerary review + suggestions?

Hey everyone planning my first trip to Japan with 2 friends and wanted to get some feedback before locking everything in.

We’re going in early September (Sept 1–14). I tried to balance culture, food, anime, and not overpacking the schedule.

✈️ Travel

  • Sept 1: Leave Orlando
  • Sept 2: Arrive Tokyo (Haneda)

🇯🇵 Tokyo (Sept 2–7)

Staying in Shinjuku

Sept 2 (arrival)

  • Shinjuku / Golden Gai (light night)

Sept 3

  • Meiji Shrine
  • Harajuku
  • Cat Street
  • Shibuya + Shibuya Sky

Sept 4

  • teamLab Planets
  • Tokyo Station / Character Street
  • Akihabara (main anime day)

Sept 5

  • Hakone day trip

Sept 6

  • Asakusa / Senso-ji (early)
  • Ueno + Ameyoko market

🇯🇵 Kyoto (Sept 7–10)

Sept 7 (arrival day)

  • Arrive from Tokyo (morning Shinkansen)
  • Nishiki Market (lunch)
  • Fushimi Inari (late afternoon)
  • Gion at night

Sept 8

  • Kiyomizu-dera (early)
  • Sannenzaka / Ninenzaka
  • Chill / cafes

Sept 9

  • Arashiyama Bamboo Grove (early)
  • Tenryu-ji
  • Monkey Park (maybe)

🦌 Sept 10 (travel day)

  • Kyoto → Nara stop (4–5 hours)
  • Nara Park / Todai-ji
  • Continue to Osaka

🇯🇵 Osaka (Sept 10–12 for me / 10–13 for friends)

Sept 10

  • Dotonbori at night

Sept 11

  • Osaka Castle
  • Kuromon Market
  • Den Den Town

Sept 12 (split day)

  • Friends → Universal Studios
  • Me → heading back to Tokyo early

🇯🇵 Tokyo (Sept 12–14)

Sept 12 (solo day)

  • Daikanyama
  • Ginza

Sept 13

  • Nakano Broadway
  • Sunshine City (Ikebukuro)

Sept 14

  • Fly out of Haneda

Questions:

  • Anything I should swap out or skip?
  • Are we missing anything major for a first trip?
  • Any food spots (especially Kyoto/Osaka) that are must-do?
  • Is Nara worth the stop or should we just go straight to Osaka?
  • Any tweaks for September weather / crowds?

Appreciate any feedback 🙏

by Jayyy_Knows