26ish Day Itinerary Check: Tokyo, Osaka/Kyoto/Kobe, Takayama/Kanazawa, Hakodate, Yamagata (with a couple day trips)

Hey y’all,

I found flights using my credit card points, so my partner and I will be going to Japan April 27th-May 23rd.

About us: mid and late 30’s, tattooed, East Coast USA. He works as a photographer and woodworker, I work at a fine-dining Japanese restaurant (think fancy sake and omakase). My brother and my best friend from high school are studying abroad in Tokyo. My partner’s old friend from college is from Tokyo, and is living there now. We also have an acquaintance in Kyoto who we might meet up with.

My brother has school until April 28th, and his flight out of Japan is May 4th. My partner and I want to visit them both while they’re there, but due to our work schedules, the very earliest we can go is April 27th. I know, I know… This puts us on the precipice of the dreaded Golden Week.

We like hiking/history/sake/food/craft. I am also really interested in Japanese hospitality, which is why I’m splurging for two Ryokans during our trip. I also love sake from Niigata and Yamagata, so I’d really like to get up there to experience the vibe of those regions.

We like to go with the flow and see where each day takes us, but I’m aware that some extra planning is required for the busy tourism season in Japan.

Any recommendations for the following itinerary? Does it seem crazy? We’ve talked about the heavy travel days… we’re both very content with reading on the train and/or staring out with window with ekiben and beers.

I’m not trying to splurge on Michelin dinners or fancy Omakases during our trip because it’s already a splurge to be traveling for so long… but any affordable places that we should check out? How do I make reservations (and do we need to??).

Okay thank you!

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Wednesday 26-Apr NJ TO NYC

Drive to Dad’s in Jersey, leave our car at his house, Dad drives us to JFK: Flight 1:20pm

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Thursday 27-Apr NYC to Tokyo (Hamacho)

Arrive 4:35pm, Pick up JR Pass, WIFI and/or Sim?, Check In

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Friday 28-Apr Tokyo (Hamacho)

OPEN. Explore/Hang with friends. Brother moves out of his dorm and checks into our hotel.

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Saturday 29-Apr Tokyo (Hamacho)

walk to woodworking tool shop/skytree/kappabashi/ueno

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Sunday 30-Apr Tokyo (Ome)

*Overnight trip with friends + brother*

AM Travel to Ome. Limestone caves, Sawanoi Brewery

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Monday 1-May Tokyo (Ome)

Ropeway and Mt. Mitake: shrine and waterfalls. PM Travel back to Tokyo.

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Tuesday 2-May Niigata Day Trip *JR pass Day 1*

Travel with friends

Northern Culture Museum, Imayo Tsukasa Sake Brewery Tour, Ponshukan at Echigo Yuzawa

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Wednesday 3-May Tokyo (Hamacho) *JR pass Day 2*

OPEN. Explore/Hang with friends. Maybe see Yokohama or Kamakura?

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Thursday 4-May Tokyo (Hamacho) *JR pass Day 3*

OPEN. Explore/Hang with friends. Brother goes back to USA.

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Friday 5-May Tokyo (Ginza) *JR pass Day 4*

Sake & Shochu Visitor Center, maybe Teamlabs? enjoy fancy hotel bath + sake bar

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Saturday 6-May Osaka (Shinsaibashi) *JR pass Day 5*

Travel to Osaka, Check in. Pinball/Ferris wheel, Night Aquarium, Dotonbori

Maybe guided lunchtime food tour?

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Sunday 7-May Kyoto (Nakagyo Ward) *JR pass Day 6*

AM shopping Osaka. PM Travel to Kyoto: explore Gion, night shrine hike?

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Monday 8-May Kyoto (Nakagyo Ward) *JR pass Day 7*

Philosopher’s walk, Maybe Fushimi for Sake

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Tuesday 9-May Kyoto (Nakagyo Ward) *JR pass Day 8*

Super early Bamboo Forest and/or Kokedera

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Wednesday 10-May Kobe (Chuo Ward) *JR pass Day 9*

Overnight trip

Travel to Kobe. Nada district, sake museum

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Thursday 11-May Kobe *JR pass Day 10*

AM Kobe Herb Gardens + woodworking museum. PM Travel back to Kyoto.

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Friday 12-May Takayama *JR pass Day 11*

AM Travel to Takayama (4 hours) Explore Takayama town, especially Antique Shop, Sake breweries

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Saturday 13-May Takayama *JR pass Day 12*

Kamikochi

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Sunday 14-May Takayama *JR pass Day 13*

Early AM: Hida no Sato. 2pm shuttle to Ryokan.

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Monday 15-May Kanazawa *JR pass Day 14*

9am shuttle back to Takayama station. Travel to Kanazawa, Kenroku-en, Myouryuji/Ninjadera? Gold leaf icecream? Samurai district?

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Tuesday 16-May Kanazawa to Hakodate *JR pass Day 15*

AM Big Travel to Hakodate (7.5 hours). See nighttime view of city Mount Hakodate Observatory

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Wednesday 17-May *JR pass Day 16*

AM Hakodate City Museum of Northern Peoples OR Goryōkaku Tower

Need to be at Otoshibe Station for pick-up service for Ginkonyu Ryokan at 2pm

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Thursday 18-May Noboribetsu *JR pass Day 17*

AM: Travel from Otoshibe Station to Hell Valley: hike and footbaths. PM travel to Hotel in Higashi-Muroran

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Friday 19-May Muroran *JR pass Day 18*

Early AM: explore cliffs around Muroran: 蓬莱門/Tokkarisho Observatory

2 PM Big Travel (7 hours) to Yamagata (staying near Yamagata Station).

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Saturday 20-May Yamagata (staying near Yamagata Station) *JR pass Day 19*

AM: Risshakuji Temple (Yamadera) cedar forest, Zao Onsen Dai Rotenburo if we feel like it

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Sunday 21-May Yamagata to Tokyo (Hamacho) *JR pass Day 20*

Afternoon Travel to Tokyo (3 hours), PM Asakusa shrine for festival

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Monday 22-May Tokyo (Hamacho) *JR pass Day 21*

Last minute shopping, packing, maybe Teamlab planets? PM final hang with friends.

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Tuesday 23-May Tokyo (Hamacho)

Final pack, Check out, explore airport, Flight at 5pm

2 comments
  1. It’s a long itinerary, so I won’t get too involved (having trouble enough planning my own!), but your mention of the Sanja Matsuri in Asakusa prompts me to suggest you get to Tokyo a day earlier to catch more of it. The Sunday evening is just the peak of a three day festival, and after being scaled back a few years running, I suspect this year will be huge. Having beers for breakfast with the locals on the Sunday morning is one of my favourite Tokyo memories. Also, if you’re into tattoos, keep in mind that the festival is one of the most Yakuza friendly, i.e. tattoo friendly. My last time was 2018, admittedly, but it was a blast.

  2. I feel like Hokkaido itself warrants a separate trip because the 7.5-9 hours spent in the train can be mentally taxing especially during peak holiday season. I get it, train travel can be very enjoyable, IF you don’t have to contend with the crowds. I would recommend keeping your destinations within Kanto/Kansai region to fully experience what the region has to offer.

    If you like woodworking, Hakone in Kanagawa could be interesting because it’s famous for [parquetry](https://allabout-japan.com/en/amp/article/1205/2/).

    Also, Nikko and Hakone have great hiking spots.

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