Honeymoon! 14 nights, first-time Japan (Tokyo → Hakone → Kyoto → Kanazawa → Tokyo), early November

Background on us: Couple in our mid-20s, honeymoon, first time in Japan. In and out of HND.
Dates: Early-to-mid November, 14 nights.
Pace/feel: Early mornings, loose afternoons. Most mornings are anchored, many days free after 4pm.
Interests: Photography, architecture, vintage/thrift, whisky, anime.
Budget: Mid-range. Mostly Hyatt points, one ryokan splurge, one nicer last night.
Constraint: Wife has a few small tattoos → ryokan needed a private in-room onsen.

Neither of us has ever been outside of North America, so advice on the schedule, as well as general etiquette would be appreciated! We already emailed all the hotels and let them know it would be our honeymoon (to try and get some free upgrades too haha).

We have global precheck (I think called global entry) and passports already, so we are good on that front.

TOKYO — 3 nights · Hyatt Regency Tokyo (Nishi-Shinjuku)
Day 1 — Arrival
Land mid-afternoon, Airport Limousine Bus to hotel

Suica + cash at airport

~19:00 Ichiran, early night

Day 2 — West side
06:30 Meiji Jingu at sunrise, buy goshuincho

08:30 Yoyogi Park

10:00 Omotesando architecture walk

12:00 Takeshita St + Brandy Melville

14:00 Shibuya vintage (Kinji, Nadia, Nuir)

16:00 Perfume blending at Yuen, Aoyama

19:00 teamLab Borderless (late slot)

Day 3 — East side
06:30 Toyosu Market, sushi breakfast

08:30 Sensoji before the crowds

10:30 Kakimori, Kuramae

13:00 Akihabara (Mandarake, Super Potato, Animate)

18:30 Omoide Yokocho

Ship suitcases ahead to Kyoto this morning — backpacks only for the mountains (takkyubin to Kyoto)

HAKONE — 2 nights (Gora) Night 1: Setsugetsuka Bettei Suiun · Night 2: Hyatt Regency Hakone
Day 4 — Into the mountains
~10:30 Romance Car from Shinjuku

12:00 Soba in Hakone-Yumoto

13:30 Tozan railway up to Gora

15:00 Ryokan check-in, private cypress onsen

19:00 Kaiseki

Day 5 — North Hakone
09:30 Hakone Museum of Art at opening (moss garden)

11:00 Sengokuhara pampas grass + Choan-ji (rakan statues)

13:00 Tofu-katsu at Tamura Ginkatsutei

15:00 Change hotels

Evening free

Day 6 — Weather Dependent → Kyoto
☀️ Clear: Izu Panorama Park via Mishima for Fuji, then Kyoto (~3hr detour)

🌧 Cloudy: Moto-Hakone torii → old Tokaido stone road on foot → Amazake-chaya (400-yr-old teahouse) → Hatajuku for yosegi marquetry → Kyoto

Either way: arrive ~18:00, Gion at lantern hour, Pontocho dinner

KYOTO — 5 nights · Hyatt Regency Kyoto (Higashiyama)
Day 7 — Inari + Nara
06:30 Fushimi Inari

09:30 JR to Nara: Todai-ji, deer, Kasuga Taisha

15:00 Back to Kyoto

Evening: ring-making workshop

Day 8 — Arashiyama + kimono hunt
07:00 Bamboo grove

08:30 Tenryu-ji at opening

10:00 Matsunoo Taisha

13:00 Gion side: vintage kimono hunt (she’ll wear it in Kanazawa), engraved chopsticks at Ichihara Heibei Shoten, hanko seals on Teramachi

16:00 Ippodo for sencha

Day 9 — Kurama → Kibune
07:30 Mochi at Demachi Masugata

08:30 Eizan line north through the maple tunnel

09:30 Kurama-dera, then the ridge trail

12:30 Lunch over the stream in Kibune

16:00 Back in the city

Evening: Eikan-do illumination if dates line up

Day 10 — Osaka day trip
09:00 Kaiyukan at opening

13:00 Amerikamura vintage

15:30 TALEX in Ikuno-ku (polarized lenses)

18:00 Dotonbori

Ship suitcases to Kanazawa this morning

KANAZAWA — 2 nights · Hyatt Centric Kanazawa
Day 11 — Transfer + weather dependent
☀️ Clear: 07:50 Thunderbird → drop bags → Shirakawa-go day trip, back ~17:00

🌧 Cloudy: slow Kyoto morning, midday train, Oyama Shrine at dusk

Crab izakaya either way

Day 12 — Kimono Photo Shoot! (We are taking our own photos)
06:45 Kenroku-en at the free early gate, before official opening

10:00 Kimono dressing + hair in Higashi Chaya

11:30 Self-shoot in the chaya lanes + Kazuemachi

14:00 Gold leaf workshop

15:30 Omicho Market

19:00 Snow crab kaiseki

TOKYO — 2 nights · The Strings by InterContinental (Shinagawa)
Day 13 — Back to Tokyo
08:00 Omicho breakfast

11:00 Shinkansen → check in ~14:30

15:30 Kichijoji: Temari no Ouchi cat cafe + Inokashira Park

17:30 Koenji for vintage

19:00 Nakano Broadway (used Seiko hunt), dinner nearby

Day 14 — Last full day
09:00 Flea market at opening

12:00 Ginza: Uniqlo sale, Itoya, Onitsuka Tiger, leather wallet

18:30 Omakase

21:00 Bar High Five → Zoetrope

Day 15 — Out
Slow morning, 16:00 late checkout

Hama-rikyu garden

Evening flight

Questions:
Day 5 — too much with a hotel change that afternoon?

Kurama → Kibune in November: is 2 hours realistic for the trail, or should I budget more?

We cut Takayama for two extra Kyoto nights. Good call? Probably too late to change it.

Swapped Shimokitazawa for Koenji + Nakano based on advice here, right move?

Been lurking for a while, so it’s nice to actually have a plan to post!

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u/BreadDead2_ — 2 days ago