JJapan Trips

14 Day Itinerary Advice/Check for First Timer

  • September 30, 2025

Hello everyone! I am going to Japan for the first time with my wife at the end of November (November 16-29). I have been working hard on an itinerary and would love to see if you all have any advice, or if anything seems unrealistic? I have a tendency to try to pack too much into days when I plan trips so am really trying not to do that here while also trying to do a lot haha. I tried to consolidate where we are staying as well because I also have a tendency to hotel/location hop. Also, we are thinking about maybe using a luggage forwarding service from Tokyo to Kyoto ~ has anyone used these before/are they reliable? Thanks in advance 😀

  • Day 1: Travel.
  • Day 2: Arrive in Tokyo in the afternoon. Check into our hotel in Shibuya and wander Shibuya until we are tired. Dinner/drinks, light shopping, etc. Early bed.
  • Day 3:
    • Asakusa (Sensoji Temple, Nakamise Shopping Street, View from Asakusa Culture Tourist Information Center.) in the AM
    • Walk from Asakusa to Ueno (maybe via the Kappabashi Kitchen Street). Spend the afternoon in Ueno (Ueno Park, Gojoten Shrine). Drinks/Dinner in Ameyoko Shopping District.
    • Then back to Shibuya to wander again until we are tired.
  • Day 4:
    • AM: Tsukiji Fish Market
    • PM: Shinjuku (Wander the streets, Shinjuku Gyoen National Garden View at top of Tokyo Metropolitan Government Building, Guided Food Tour in the evening)
  • Day 5:
    • 10 AM: TeamLabs Planets
    • Afternoon: Harajuku (Takeshita Street, Omotesando Yoyogi Park -> Meiji Shrine) & Shibuya (Shibuya crossing, Hachiko statue,)
    • Maybe try to get into Shibuya Sky at sunset
  • Day 6:
    • Morning train from Tokyo to Hakone.
    • Hakone Loop
  • Day 7:
    • AM: Hike in Hakone (I'm thinking the Mt. Kintoki hike)
    • PM: Onsen, either in town or at our ryokan
  • Day 8:
    • AM: Travel from Hakone to Kyoto
    • Gion District, Higashiyama District
    • PM: Illumination event at Kiyomizu-dera Temple?
  • Day 9:
    • AM: Bike tour of Arashiyama area
    • PM: Kinkaju-Ji, Ryoanji Temple
      • Dinner in Pontocho Alley
  • Day 10:
    • AM: Walk to top of Fushimi Inari Shrine
    • Nishiki Market
    • PM: Hozugawa River Boat Ride? (not sure about this excursion yet) OR Philosopher's Path
  • Day 11:
    • Day trip from Kyoto to Osaka (Osaka Castle (just touring the grounds), Shitenno-Ji Temple, Isshin-Ji Temple, Namba Yasaka Jinja Temple Umeda Sky Building Shinsekai Market, Kuromon Ichiba Market Dotonbori)
      • Food Tour in the evening
  • Day 12:
    • Day trip from Kyoto to Nara (Nara Park, walk to top of Mt. Wakakusa, Todaiji Temple,Kofukuji Temple, Naramachi)
  • Day 13:
    • AM: Train from Kyoto to Tokyo
    • Staying in Asakusa, so spend the rest of the day wandering this area, shopping, etc.
  • Day 14: Travel home.

by Ok_Distribution9310