JJapan Trips

Japan itinerary check/advice

  • January 26, 2026

Hi everyone!

My boyfriend and I are planning our second trip to Japan (20 days, late Sept/early Oct).

Context:

  • Past travels: We have already done the classic "Golden Route" (Tokyo, Osaka, Kyoto) plus Kanazawa, Hiroshima, and Miyajima.
  • This trip's goal: We want to explore the North (Hokkaido), the Japanese Alps (Takayama/Matsumoto), and the Izu Peninsula, while mixing in a few specific spots we missed or want to revisit in Tokyo/Kyoto.
  • Pacing: We are okay with moving around, but want to make sure the "travel days" aren't impossible.

Here is the plan we’ve drafted. We’d love a sanity check, specifically on the transfers between regions. The daily schedule is not something set in stone, and we always have room for adjustments depending on mood, energy levels, and just generally what we feel like doing.

Part 1: Tokyo

  • Day 1 (Sep 20): Land Haneda. Shibuya crossing & dinner.
  • Day 2 (Sep 21): DisneySea. May change the day we do this.
  • Day 3 (Sep 22): Meiji shrine & Gotokuji (Cat Temple).
  • Day 4 (Sep 23): Asakusa/Nakamise and Akihabara. Maybe instead go Nikko.

Part 2: Hokkaido (First time here)

  • Day 5 (Sep 24): Fly Haneda -> New Chitose (Sapporo). Ramen alley (Susukino).
  • Day 6 (Sep 25): Day trip to Otaru (Canal, Glass Arts, Sushi).
  • Day 7 (Sep 26): Sapporo sity (Nijo Market, Beer Museum, Genghis Khan BBQ).
  • Day 8 (Sep 27): Train to Noboribetsu (Hell Valley). Onsen stay.

Part 3: Kansai stopover

  • Day 9 (Sep 28): Long travel day. Train to Chitose airport -> Fly to Osaka -> Travel to Kyoto.
    • We’ve seen the main temples in Kyoto before, and spent 6 nights there. This night is just for a Gion stroll.
  • Day 10 (Sep 29): Morning train to Himeji Castle (missed this last time). Evening back in Kyoto for Pontocho alley.
  • Day 11 (Sep 30): Travel to Takayama: Shinkansen to Nagoya -> Hida express. Hida beef dinner.

Part 4: The Alps & Shuzenji

  • Day 12 (Oct 1): Day trip to Matsumoto Castle (Bus/Train?).
  • Day 13 (Oct 2): Bus to Shirakawa-go village. Sake tasting in Takayama.
  • Day 14 (Oct 3): Strict timing. Train via Nagoya to Shuzenji (Izu). We are thinking of booking a private Onsen and want to leave Takayama by 8 AM to make check-in.

Part 5: Kamakura & Tokyo

  • Day 15 (Oct 4): Train to Kamakura. Great Buddha/Hasedera.
  • Day 16 (Oct 5): Enoshima tram & Island. Return to Tokyo.
  • Day 17 (Oct 6): Chill/Flexible day in Tokyo.
  • Day 18 (Oct 7): Yokohama day trip (Cup noodles, Chinatown).
  • Day 19 (Oct 8): PokePark. May change the day we do this, if at all.
  • Day 20 (Oct 9): Fly home.

Specific Questions:

  1. Takayama as a base: We are sleeping 3 nights in Takayama (Days 11, 12, 13). Is doing a round-trip to Matsumoto from Takayama on Day 12 too much travel for one day? We really want to see the castle.
  2. Hokkaido timing: Is late September a decent time for Sapporo/Noboribetsu? We aren't expecting fall colors yet, but hoping the weather is pleasant.
  3. Himeji: We really want to see Himeji since we didn't have the chance last time. We know it's a big detour but we also loved Kyoto so revisiting is a win for us.
  4. Any other advice you might have on the itinerary, we would be really grateful.

Thanks in advance!

by Em_N