14 Day Itinerary – Tokyo/Nagano Prefect/Kyoto/Osaka

My wife and I (40s) are travelling to Japan for the first time during the first two weeks of April 2026, so a lot of the itinerary may be standard first time spots with a focus on the cherry blossoms. We are travelling to Nagano and staying in Yamanochi to visit the snow monkeys, hot springs, and hike the mountains, and I would love any tips or hikes for that portion of the trip. Also, any advice on which temples to prioritize based on day/section in Kyoto would be great.

I did look at the JR website and it mentioned that I wouldn't need a JR Pass but could benefit from regional passes. It looked like the pass for the Shinkansen to Nagano wouldn't allow me to use it for the Osaka to Tokyo route, so I was thinking I would just book the individual train/metro tickets, unless this sub thinks getting multiple regional JR passes would make sense.

Appreciate any thoughts!

(note: a question marks indicates can do if time permitting but not prioritized, so any thoughts on those would be great)

Days 1–3: Tokyo

Day 1:

  • Land at 3pm at NRT
  • Take Limo Bus (reserve 3 months in advance) or train to Shinjuku Station
  • Check-in to hotel (Shinjuku)
  • Golden Gai and Omoide yokocho

Day 2:

  • Shinjuku Gyoen National Garden
  • Explore Shibuya Crossing and Meiji Shrine; Harajuku’s Takeshita Street?,
  • Shopping: cosme TOKYO, ⁠vintage shopping in Shimokitazawa (or "Shimokita"), MEGA Don Quijote Shibuya?

Day 3:

  • TeamLab Borderless
  • Imperial Palace & Gardens and Chidorigafuchi Park

Day 4-6: Nagano (Jigokudani and Chubu-Sangaku)

Day 4:

  • Train Tokyo → Nagano (~2 hrs by Shinkansen)
  • Rent car
  • Check-in to Hotel (Yamanochi)

Day 5:

  • Visit Jigokudani National Park, Matsumoto Castle?

Day 6:

  • Visit Chubu-Sangaku/Kamikochi, Chubusangaku National Park (Yari-Hotaka Range)
    • Nakasendo: Torii Pass, Myojin Ike Pond Loop

Days 7-9: Kyoto

Day 7:

  • Return Rental Car
  • Train to Kyoto (3.5-4 hours by Shinkansen)
  • Check-in to Hotel (Nakagyo Ward, Kamiosakacho)
  • Fushimi Inari Taisha
  • Jukkoku-Bune Boat Tour
  • Sanjūsangendō Temple?
  • Dinner in Pontocho Alley 

Day 8:

  • Maruyama Park and Gion district; tea ceremony?
  • Nanzenji Temple, Kodai-ji Temple and Kiyomizu‑dera Temple (Probably not all)
  • Philosopher’s Path
  • teamLab Biovortex?

Day 9

  • Daikaku-ji, Tenryu-ji, Kinkaku-ji (Probably not all)
  • Arashiyama Bamboo Grove (and monkey park?) and/or Adashino Nenbutsuji Temple, Otagi Nenbutuji?
  • Shopping/Relax
  • Kuramadera?

Days 10-11: Osaka

Day 10:

  • Train Kyoto → Osaka
    • OR train to Nara: Nara Park with deer and cherry blossoms. Todaiji Temple?
    • Or train Uji and byodo-in temple?
  • Check-in to hotel (Abenobashi area)
  • Shopping
  • Shinsekai area for dinner

Day 11:

  • Osaka Castle and Park: 
  • Kema Sakuranomiya Park: 
  • Dotonbori street food (takoyaki, okonomiyaki). 
  • Umeda Sky Building?

Day 12-14: Tokyo

Day 12:

  • Train to Tokyo
  • Check-in to hotel (Minato City)
  • TeamLab Planets?
  • Tsukiji Outer Market

Day 13:

  • ⁠Ueno Park
  • Ueno Ameyoko shopping and market
  • Tokyo National Museum?
  • Tokyo Skytree?
  • Nakamise street?

Day 14

  • Head spa/massage
  • Fly out at 4:30pm from HND

by MilkComfortable4749