13-Day Japan Itinerary (Osaka → Kyoto → Hakone → Tokyo) – Seeking Advice on Pacing & Luggage Management

Hi everyone!

We’re planning a 13-day trip to Japan (Osaka → Kyoto → Hakone → Tokyo, with a day trip to Nikko) and would love some feedback on our itinerary. We’re already used to walking a lot and being tired from long days of sightseeing, so we’re okay with physically demanding schedules, but we really want to explore as much as possible since this might be our only trip to Japan.

Some concerns we have:

  • We’ll be traveling with two big suitcases, so we’re worried about managing them while catching trains and transferring between cities. What’s the most practical way to get around Japan efficiently with large luggage—especially when hopping between Osaka, Kyoto, Hakone, and Tokyo? Any tips for minimizing stress with luggage while still hitting as many sights as possible?
  • Are there any parts of our itinerary that feel too rushed, or any logistics (like train connections or sightseeing order) that could cause issues?

We’d really appreciate any advice or suggestions for optimizing our route while still being able to see a lot. Thanks in advance!

Day 1 – Sept 12 (Thu): Arrival in Osaka

  • 15:50 – Land at KIX
  • 17:00 – Nankai Airport Express to Namba (~45 min) or Limited Express “Rap:t” (~35 min)
  • 19:00 – Check-in
  • 20:00 – Dinner: Ajinoya okonomiyaki
  • 21:00 – Explore Dotonbori

Overnight: Osaka

Day 2 – Sept 13 (Fri): Osaka Vibes

  • 09:30 – Osaka Castle & Park
  • 10:45 – Metro to Kuromon Market
  • 11:00–12:30 – Snack lunch
  • 12:45 – Metro to Shinsekai
  • 13:00–14:30 – Explore Shinsekai + Tsutenkaku
  • 14:45 – Train to Amerikamura
  • 15:00–20:00 – Shops, coffee, dinner
  • 20:00–21:30 – teamLab Botanical Garden Osaka

Overnight: Osaka

Day 3 – Sept 14 (Sat): Kyoto Highlights

  • 09:00 – JR Special Rapid to Kyoto (~30 min)
  • 10:00 – Drop bags at hotel
  • 10:30 – Kiyomizu-dera
  • 12:00 – Walk Sannenzaka & Ninenzaka
  • 13:00 – Lunch at Izuju Sushi
  • 14:30 – Yasaka Shrine
  • 15:30 – Explore Shijo / Kawaramachi
  • 18:00 – Stroll Pontocho Alley
  • 19:30 – Dinner riverside

Overnight: Kyoto

Day 4 – Sept 15 (Sun): Kyoto Icons

  • 09:00 – Train to Fushimi Inari Taisha
  • 09:30–11:00 – Torii trails
  • 11:30 – Brunch
  • 12:30 – Bus/taxi to Kinkaku-ji
  • 13:30–14:30 – Visit Kinkaku-ji
  • 15:00 – Taxi to Nijō Castle
  • 15:30–17:00 – Explore castle
  • 17:15 – Train to Nishiki Market
  • 17:30–19:00 – Snack dinner & browsing

Overnight: Kyoto

Day 5 – Sept 16 (Mon): Arashiyama + Travel to Hakone

  • 08:30 – Train to Arashiyama
  • 09:00–11:30 – Bamboo Grove, Tenryu-ji, Togetsukyo Bridge
  • 12:00 – Lunch
  • 13:00 – Collect bags
  • 13:30 – Shinkansen to Odawara (~2 hrs)
  • 15:30 – Hakone Tozan Line to Gora (~40 min)
  • 18:00 – Check-in at ryokan
  • Onsen soak + kaiseki dinner

Overnight: Hakone

Day 6 – Sept 17 (Tue): Hakone → Tokyo

  • 08:30 – Check-out, leave luggage
  • 09:00 – Ropeway to Owakudani
  • 11:00 – Lake Ashi cruise + Hakone Shrine
  • 13:00 – Lunch
  • 14:00–16:00 – Hakone Open-Air Museum
  • 16:30 – Collect luggage
  • 17:00 – Train to Shinjuku (~2 hrs)
  • 21:00 – Dinner in Omoide Yokocho
  • 22:00 – Walk Kabukicho

Overnight: Tokyo

Day 7 – Sept 18 (Wed): Harajuku & Shibuya

  • 10:00 – Meiji Shrine + Yoyogi Park
  • 12:00 – Takeshita Street
  • 13:00 – Lunch in Omotesando
  • 14:30 – Explore Cat Street
  • 16:30 – Hachiko Square + Shibuya Crossing
  • 18:00 – Sunset at Shibuya Sky
  • 20:00 – Drinks at Nonbei Yokocho

Overnight: Tokyo

Day 8 – Sept 19 (Thu): Tokyo Culture & Subculture

  • 09:30 – Senso-ji Temple
  • 11:00 – Shop Nakamise-dori
  • 12:00 – Tokyo National Museum (Ueno Park)
  • 13:30 – Lunch in Ueno
  • 15:00–17:30 – Akihabara
  • 19:00 – Dinner at Tsukiji Outer Market

Overnight: Tokyo

Day 9 – Sept 20 (Fri): Day Trip to Nikko

  • 07:30 – Train to Nikko (~2 hrs)
  • 10:00 – Toshogu Shrine, Shinkyo Bridge
  • 13:00 – Walk Kanmangafuchi Abyss
  • 15:00 – Return to Tokyo
  • 18:00 – Dinner

Overnight: Tokyo

Day 10 – Sept 21 (Sat): Shimokitazawa + Ginza

  • 10:00 – Brunch in Shimokitazawa
  • 13:00 – Explore Ginza
  • 16:00 – Optional: teamLab Planets
  • 19:00 – Rooftop dinner / jazz bar

Overnight: Tokyo

Day 11 – Sept 22 (Sun): Chill + Revisit or Sumo Tournament

  • 10:30 – Shinjuku Gyoen
  • 13:00 – Coffee + snack
  • Afternoon – Revisit favorite neighborhoods (Nakameguro, Shimokitazawa) or Sumo Tournament
  • 18:00 – Optional dinner cruise / izakaya hunt

Overnight: Tokyo

Day 12 – Sept 23 (Mon): Final Shopping

  • 10:00–15:00 – Shopping: Tokyu Hands, Loft, Uniqlo Flagship, Don Quijote
  • 15:30 – Final sushi lunch / omakase
  • 17:30 – Pack + relax

Overnight: Tokyo

Day 13 – Sept 24 (Tue): Departure

  • 10:00 – Check-out
  • 12:00 – Transit to airport (~1 hr)
  • 17:30 – Depart Japan

by Sea_Celebration4003