First-time Japan trip (20 days) – Itinerary check

Hi everyone!

This will be my first trip to Japan, and I’d really appreciate feedback on my itinerary.

All hotels are already booked. I tried to plan each day realistically by grouping nearby areas, defining clear walking routes, and leaving evenings open in days where night exploration is the goal.

We’re two guys in our late 20s, aiming for a medium to intensive pace. We’re interested in first-time highlights, architecture, old vs. modern Japan, street food, geek culture, and night city vibes. No theme parks planned.

Trip overview

Dates: March 16 – April 4, 2026
Arrival: Haneda Airport – Mar 16 ~07:35
Departure: Haneda Airport – Apr 4 ~13:05

Confirmed bases

Tokyo: Mar 16–21 (Iidabashi area)

Kanazawa: Mar 21–23

Takayama: Mar 23–25

Osaka: Mar 25–Apr 1 (Namba area)

Tokyo: Apr 1–4 (Shinjuku / Kabukicho area)

All other locations are day trips from these bases.

Itinerary

Mar 16 – Arrival / Tokyo (Iidabashi → Marunouchi → Shinjuku)

Morning: Arrive at Haneda 07:35 → train to Iidabashi area (~09:00) → luggage drop, shower, rest.
Afternoon: Tokyo Station → Marunouchi side walk (Marunouchi Brick Square, Tokyo International Forum exterior, station food halls).
Night: Shinjuku walk: Kabukicho streets → Omoide Yokocho → ramen near Shinjuku Station.

Mar 17 – Tokyo East (Asakusa → Ueno → Akihabara)

Morning: Asakusa: Sensō-ji → Nakamise Street → Shin-Nakamise shopping streets.
Afternoon: Walk/metro to Ueno → Ueno Park paths → Ameyoko Market (street food lunch).
Night: Akihabara: Radio Kaikan → arcades (SEGA/GiGO-style buildings) → neon streets around Chuo-dori.

Mar 18 – Tokyo West (Meiji → Harajuku → Shibuya)

Morning: Meiji Shrine → walk through Yoyogi Park toward Harajuku exit.
Afternoon: Harajuku: Takeshita Street → Cat Street → Shibuya PARCO.
Night: Shibuya: Shibuya Crossing → Center Gai → Miyashita Park rooftop → izakayas nearby.

Mar 19 – Kamakura day trip

Early start (~05:30–06:00).
Morning: JR Yokosuka Line to Kamakura (~1h) → Komachi-dori (breakfast) → Tsurugaoka Hachimangu.
Afternoon: Bus/train to Hase → Hase-dera → Kotoku-in (Great Buddha) → Enoden Line ride (Hase → Kamakurakōkō-mae).
Evening: Walk to Shichirigahama Beach for sunset or continue to Enoshima Island.
Night: Return to Tokyo (~19:30–20:30).

Mar 20 – Mt. Fuji day trip (Hakone OR Kawaguchiko – TBD)

Very early start (~05:00).

If Kawaguchiko:
Tokyo → Kawaguchiko → Lake Kawaguchi walk → Oishi Park → Mt. Fuji Panoramic Ropeway → lakeside return walk.

If Hakone:
Tokyo → Hakone-Yumoto → Hakone Ropeway → Owakudani → Lake Ashi boat → Hakone Shrine area.

Night: Return to Tokyo early evening.

Mar 21 – Tokyo → Kanazawa

Morning: Hokuriku Shinkansen Tokyo → Kanazawa (~2.5h).
Afternoon: Check-in → Higashi Chaya District walk (tea houses, side streets, cafés).
Night: Dinner around Omicho Market area.

Mar 22 – Kanazawa

Morning: Kenroku-en Garden → Kanazawa Castle grounds.
Afternoon: Omicho Market (lunch) → Nagamachi Samurai District walking route.
Night: Local izakaya near hotel.

Mar 23 – Kanazawa → Shirakawa-go → Takayama

Morning: Bus Kanazawa → Shirakawa-go (~1h15).
Afternoon: Walk Ogimachi village → Shiroyama viewpoint → village streets.
Evening: Bus Shirakawa-go → Takayama → Sanmachi Suji old town walk.

Mar 24 – Takayama

Morning: Miyagawa Morning Market → old town streets.
Afternoon: Higashiyama walking course (temples loop).
Night: Hida beef dinner.

Mar 25 – Takayama → Osaka

Morning: Takayama → Nagoya → Osaka by train (~4h total).
Afternoon: Check-in Namba area → short rest.
Night: Dotonbori walk: canal → Glico sign → street food stalls.

Mar 26 – Osaka (Namba → Shinsaibashi → America-mura)

Morning: Kuromon Ichiba Market.
Afternoon: Walk Kuromon → Shinsaibashi-suji → America-mura streets.
Night: Namba izakayas or return to Dotonbori.

Mar 27 – Kyoto day trip (Higashiyama route)

Early start (~05:30–06:00).
Morning: Osaka → Kyoto → Kiyomizudera.
Afternoon: Walk downhill via Sannenzaka → Ninenzaka → Yasaka Shrine → Gion streets.
Night: Return to Osaka.

Mar 28 – Kyoto day trip (Fushimi Inari → Central Kyoto)

Early start (~05:00).
Morning: Fushimi Inari Taisha (up to mid-trail viewpoint).
Afternoon: Train to central Kyoto → Nishiki Market → Teramachi/Shinkyogoku arcades → Kamo River walk.
Night: Pontocho Alley → return to Osaka.

Mar 29 – Kyoto day trip (Arashiyama)

Morning: Bamboo Grove → Tenryu-ji → Togetsukyo Bridge.
Afternoon: Katsura River area → cafés → return to Kyoto Station.
Night: Return to Osaka.

Mar 30 – Nara day trip

Morning: Osaka → Nara → Nara Park → Todai-ji.
Afternoon: Walk to Kasuga Taisha via forest paths → Naramachi streets.
Night: Return to Osaka.

Mar 31 – Osaka (Castle → Umeda)

Morning: Osaka Castle Park (outer grounds).
Afternoon: Umeda area (department stores, architecture).
Night: Umeda Sky Building → final Osaka dinner.

Apr 1 – Osaka → Tokyo (Shinjuku)

Morning: Shinkansen Osaka → Tokyo (~2.5h).
Afternoon: Check-in Shinjuku/Kabukicho → rest.
Night: Kabukicho → Golden Gai → late ramen.

Apr 2 – Tokyo (Minato → Odaiba → Roppongi)

Morning: Zojo-ji Temple → Tokyo Tower exterior.
Afternoon: teamLab Planets (Toyosu) → Odaiba waterfront walk.
Night: Roppongi Hills → skyline views.

Apr 3 – Tokyo (Shimokitazawa → Shibuya → Shinjuku)

Morning: Shimokitazawa (thrift stores, cafés).
Afternoon: Shibuya shopping (PARCO / Loft / Hands).
Night: Final Shinjuku night walk (Kabukicho → Omoide Yokocho).

Apr 4 – Departure

Train to Haneda → flight at 13:05.

Main questions

Given this route + multiple day trips, would a 14-day JR Pass make sense, or are individual tickets + IC card more cost-effective?

Is it common and reliable to forward suitcases directly from Kanazawa to Osaka, skipping Takayama, and do Shirakawa-go with just a backpack?

Is it realistic to decide between Hakone and Kawaguchiko only 1 or 2 weeks before the trip, based on Mt. Fuji visibility, without risking sold-out transport?

Thanks a lot in advance, any feedback or corrections are very welcome.