14 Day Tokyo/Osaka/Hokkaido Itinerary Advice Needed!

Hi guys!

Heading to Japan early next month and would love some advice on our current itinerary, particularly whether some days are too ambitious or unrealistic time-wise.

Most of our bookings are already locked in (flights, Tokyo/Osaka, Kiroro), although some accommodation is still refundable if tweaking the plan would make things smoother. Niseko is the main flexible part — I know it’s pretty overcrowded these days and often a big avoid on Reddit, but we’re still keen to experience ski-in/ski-out at least once (looking at Hilton Niseko). We’re doing Kiroro first to hopefully enjoy quieter, more peaceful snowboarding before heading there.

We’d especially love help with:

  • Whether certain days are overpacked
  • Additional activity ideas (especially in Tokyo & Day trip from Otaru)
  • Food recommendations we shouldn’t miss

If anyone has done a similar route (Tokyo → Osaka → Hokkaido in winter), we’d really appreciate your insight. Thanks so much!

📍 Tokyo (Feb 10–14) – Staying in Shinjuku East

Feb 10 – Arrival

  • Arrive in the afternoon at Narita Airport
  • Train to Shinjuku East
  • Easy dinner + rest

Feb 11 – Shibuya / Harajuku

  • Meiji Jingu Shrine
  • Shibuya 109
  • Shibuya sky in the evening

Feb 12 – Ginza & Tokyo Bay

  • Tokyo Bay go-karting (Unsure whether to still do this based upon reviews/upsetting locals)
  • Ginza Six

Feb 13 – DisneySea

  • DisneySea (full day)

📍 Osaka (Feb 14–17)

Feb 14 – Travel to Osaka

  • Early Shinkansen (hoping to see Mt Fuji on the way)
  • Check in to Hotel Monterey Le Frere (~11am)
  • Nara Deer Park for the afternoon
  • Todaiji and Kasuga Taisha temples
  • Back to Osaka to explore in the evening

Feb 15 – Universal Studios

  • Universal Studios Japan (full day)

Feb 16 – Osaka & Nara

  • Osaka Temple
  • Osaka Aquarium
  • Shopping/Explore

📍 Hokkaido – Otaru / Kiroro / Niseko (Feb 17–25)

Feb 17 – Otaru

  • Fly Osaka → Sapporo (arrive ~12pm)
  • Train to Otaru (arrive ~1pm) and check in to Granbell Hotel
  • Otaru Canal
  • Explore town + dinner

Feb 18 – Day Trip

  • Asari Station (early 7:30am)
  • Unsure what would be best to do for the day here before evening Ice festival
  • Lake Shikotsu Ice Festival late afternoon

Feb 19 – Kiroro

  • Early transfer to Kiroro – Hopi hill Farmstay
  • Snowboarding – Day 1

Feb 20 – Kiroro

  • Snowboarding – Day 2

Feb 21 – Kiroro

  • Snowboarding – Day 3

Feb 22 – Niseko

  • Transfer to Niseko
  • Snowboarding – Day 4

Feb 23 – Niseko

  • Snowboarding – Day 5

Feb 24 – Niseko

  • Snowboarding – Day 6

Feb 25 – Departure

  • Afternoon flight home from CTS ✈️

by Accomplished_Ice4367