Winter Itinerary 2023 – Osaka, Kyoto, Tokyo, Sendai, Hakodate and Sapporo +Day trips

The title pretty much sums it up!

My partner and I have been planning a 1-month long trip to Japan this winter. We have been planning this trip for years, but it’s actually happening this year. It’ll be my second time in Japan and my partner’s first time out of the state (!). We’re in our mid 20’s, LOVE food, culture, nature, music and animals. We also are pretty big party goers.

I’ve planned a pretty detailed itinerary, but this is mostly because the last time I planned absolutely nothing and felt like I barely scratched the surface (and did barely anything that I wanted to). This time, we’ve got a detailed plan but it’s going to be used as a guide so we can still be spontaneous!

I’m mostly asking if this itinerary is way too chock full of stuff, and for activity/food recommendations. It’s a long one, so I appreciate you sticking with it!

Notes: We’re getting the 21 day JR pass each. Went to Disneyland last time and definitely had my fill.

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Day 1 – Osaka (Dōtombori) – 20th December
Fly into Kansai around 6. Take train or airport bus to hotel in Dotombori. Get dinner and explore.

Day 2 – Osaka (Dōtombori) – 21st December
Just explore the area. No set activities. Ideas: Amerikamura, Shinsaibashi-Suji. Go up Tsutenkaku at sunset, then explore Shinsekai. get dinner here or Dotombori.

Day 3 – Osaka (Dōtombori) – 22nd December
Nothing planned for the day. Perhaps go to cup noodle museum and Minoh park, or Nara day trip.

Day 4 – Osaka (Dōtombori) – 23rd December
Get up late if we feel like it, find a nice coffee and something greasy to eat for breakfast. head to Umeda to explore and shop. Head to Tennoji park, maybe go to Tennoji zoo. Finish up the day with Abeno Harukas, try and get there before the art gallery closes. Watch sunset from deck. Drop shopping back home and go out for dinner/drinks (stop in at Hozenji perhaps?).

Day 5 – Osaka (Dōtombori) – 24th December (Christmas Eve)
Head to Osaka Castle, and explore the area around it. Lots of cool stuff. Try and get KFC special Christmas meal for lunch? Do Tempozan ferris wheel this evening. Walk along the pier, Tempozan Harbor Village for romantic dinner (suggestions welcome) and back to Dotonbori for drinks. Maybe really nice sushi? Mmmm

Day 6 – Osaka (Dōtombori) – 25th December (Christmas)
My partner is planning what we do today 🙂

Day 7 – Osaka (Dōtombori) to Kyoto (Kawaramachi) – 26th December
Take bullet train to Kyoto (0.5 hr) in the morning. Dump bags at hotel and explore Kyoto. Stay in Kawaramachi. Walk to: • Kiromizu-dera • Hokan-ji Temple • Gion • Yasaka-jinja shrine • Hanamikoji street • Wrap up at Pontocho Ally

Day 8 – Kyoto (Kawaramachi) – 27th December
Wake up really early to see streets of Kyoto without crowds. Head to Nanzen-ji temple (walk or take train), then go down Philosopher’s path, heading to Okazaki-jinja Shrine. Could then catch a train to Imperial palace and then Kinkaku-ji, or we could head home, drop the shopping off and go on a bar hop after dinner (bar ideas: in the Moon, RUB A DUB and bar moon walk).

Day 9 – Kyoto (Kawaramachi) – 28th December
Take public transport to Arashiyama Bamboo Grove first thing to beat the crowds. Then; • Tenryu-ji • Sagano Romantic train • Arashiyama Monkey Park • Togetsukyo bridge (lunch) Then start to head home via Kinkaku-ji and the Imperial Palace. Find a yummy dinner (suggestions welcome) and a drink or 2.

Day 10 – Kyoto (Kawaramachi) – 29th December
Head to Fushimi Inara as early as possible. Take our time there and get lunch in the area (maybe go to a cat cafe). Head to Uji, and explore Byodo-in Temple. take our time here too then wander back near our hotel for our last night in Kyoto.

Day 11 – Kyoto (Kawaramachi) to Tokyo (Shinjuku) – 30th December JR day 1
In the morning do the things we’ve missed (possibly Tofuku-ji and Higashi Hogan-ji). Then take bullet train (2.5 hrs) to Shinjuku. Dump our bags and explore. Any good dinner suggestions?

Day 12 – Tokyo (Shinjuku) – 31st December – NYE JR day 2
Spend day exploring at our own pace. Any recommendations? We’re aware that most things will be closing down for the NY break.

Start out the night in Rappongi or just dinner/lunch in Rappongi (soba?), move on to Shibuya for bars (and shibuya crossing at midnight). Stay out and get cab home or rush for last train, and if we’re still going, then to Shinjuku for late night (Recommended clubs: Circus Tokyo, Kagurane, Atom Tokyo). Lots of options. ZeroTokyo, kabukicho tower. Check events closer to date 😉

Day 13 – Tokyo (Shinjuku) – 1st January – NY JR day 3
Get ourselves up to go have a breakfast buffet at the Park Hyatt Tokyo (book soon). Have a lazy day, visit the first shrine of the year (any recommendations?). Then explore Takadanobaba. Grab dinner from a konbini or fast food.

Day 15 – Tokyo (Shinjuku) – 2nd January JR day 4
No strict plans for this day, could go up tokyo sky tree (has been open on 1/1 in the past) and checkout Harajuku and/or Meguro City, or even Yokohama (chinatown and gundam)

Day 16 – Tokyo (Shinjuku) to Yudanaka – 3rd January JR day 5
In the morning go explore Omiya Bonsai Village Leave from Shinjuku (in the afternoon) for Yudanaka (3.5 hrs) to stay at an onsen (Yudanaka Onsen Yamazakiya or Hotel Housei)

Day 17 – Yudanaka – 4th January JR day 6
Onsen and snow monkey park

Day 18 – Yudanaka to Tokyo (Shimbashi) – 5th January JR day 7
Leave from Yudanaka for Shimbashi (3.5 hrs). Dump bags, try to get tickets for Ghibli museum this day? Explore at night

Day 19 – Tokyo (Shimbashi) – 6th January JR day 8
Mishima day trip (1.5 hours each way). Is this worth it? Instead, we could do Tokyo national museum and Ameyoko market.

Day 20 – Tokyo (Shimbashi) – 7th January JR day 9
Hakone day loop if we’re feeling keen. We don’t have to do everything on the loop if it’s too much.

Day 21 – Tokyo (Shimbashi) to Sendai – 8th January JR day 10
Take bullet train in the morning to Sendai (2 hrs). Dump bags and start exploring. Any recommendations for dinner? • Sendai castle ruins • Sendai city Tomizawa site museum • Tohoku University

Day 22 – Sendai – 9th January JR day 11
Travel to Yamadera in the morning (1 hr). Shrines and retro museum. Get brekky here. Come back by lunchtime. Then go to Matsushima (0.5 hr). Could take a ferry around the islands, check out Entsuin, and head to Shiogama for dinner (Sushi! Any idea recommendations?). Make our way back.

Day 23 – Sendai to Hakodate – 10th January JR day 12
Head to Hakodate in the morning (3 hrs). Tokyustay Hakodate Asaichi Akarinoyu – Beautiful view from roof & cheap, less than $100. Drop bags off, grab lunch and then head to Hakodate tropical botanical gardens. Then make our way to hakodate asaichi, and then attempt to hike Mount Hakodate at sunset. Head out to Motomachi and the red brick warehouse (find dinner somewhere here). Come back and collapse in bed.

Day 24 – Hokadate to Lake Toya – 11th January JR day 13
Head to Lake Toya in the morning, stopping off at Onuma Quasi-National Park (2 hrs). Check into hotel and chill out. Do the Kompirayama walking trail if feeling up to it. This hotel: Beautiful views. only $282

Day 25 – Lake Toya to Sapporo – 12th January JR day 14
In the morning head up Usuzan Ropeway (volcano!!). Then come back to pick up bags, there should be a shuttle to Toya station. From Toya station to Sapporo (2 hrs). Just chill in Sapporo once we get there (staying near Susukino)

Day 26 – Sapporo – 13th January JR day 15
Explore Moerenuma park in the morning, then head to sapporo beer museum and then Fushimi Inari shrine. Head to Susukino for dinner and drinks.

Day 27 – Sapporo – 14th January JR day 16
Explore the Historical Village of Hokkaido. Get lunch in ramen alley. Back to Susukino for the night?

Day 28 – Sapporo – 15th January JR day 17
Otaru day trip (1 hr each way)

Day 29 – Sapporo to Osaka (Umeda) – 16th January JR day 18
Fly from Sapporo to Osaka (100 bucks) in the morning. Explore Umeda today/tonight.

Day 30 – Osake (Umeda) – 17th January JR day 19
Hiroshima day trip.

Day 31 – Osaka (Umeda) – 18th January JR day 20
Kobe day trip

Day 32 – Osaka (Umeda) – 19th January JR day 21
Universal studios

Day 33 – Osaka (Umeda) – 20th January
Last day! Stay tonight in special romantic hotel in Dotombori.

Day 34 – Osaka (Umeda) – 21st January Fly out!

1 comment
  1. * Sounds like waaay too many days in Osaka. It’s fine if you want to take it slow, but you’d probably want to add a couple more day trips to nearby places like Himeji castle (with Kobe) or Koyasan.
    * Might want to spend a day in Nara as well?
    * There isn’t much (if at all) to do on NYE. People stay at home and watch TV lol. You can actually do Hatsumode past midnight, though the crowd might be unbearable.
    * First time I’ve ever heard anyone want to explore Takatanobaba… Not much there, especially now that Narikura had closed.
    * If you can, *definitely* try to grab a night in Ginzan Onsen enroute to Sendai. The winter vibe there is unparalled.
    * Goryokaku is usually the recommended attraction in Hakodate, though just go up the observation tower to the side, you can’t really see much within the complex.

    In general, it still feels much, much too easy with days not really going anywhere. Again, there’s nothing wrong with that, but you can almost certainly plan *a lot* more interesting places into the trip, especially that you mentioned you felt you barely scratched the surface last time.

    Takayama / Shirakawa-go in winter should be fun, Kawaguchiko lake and Nikko are great side trips from Tokyo, and there are some interesting alternatives in Tohoku if you give it a day or two, such as Kakunodate and riding the Akita Nairiku line rail.

    It’s guess it’s really down to whether a trip to Japan is easy for you. If getting to Japan is rather difficult, I’d say pack it tighter to see more. If you’re confident that you can do other more specific areas of Japan easily in the future, then this itinerary works.

    I’m somewhat doubting if the 21 day JR pass is worth it, especially given that you aren’t using it to return from Sapporo to Kansai. A combination of the [Hokuriku Arch pass](https://www.westjr.co.jp/global/en/ticket/hokuriku-arch-pass/) (which itself gives you some interesting alternative destinations), [JR East / South Hokkaido Pass](https://www.jreast.co.jp/multi/en/pass/easthokkaido.html), and [Hokkaido Rail Pass](https://www.jrhokkaido.co.jp/global/english/ticket/railpass/index.html#hrp) might do the job slightly cheaper within the restraints of their respective time limits, but the Hiroshima portion won’t be included. Of course, there’s the sense of ease that comes with not having to worry about train tickets for 21 days, and that can easily be worth the difference.

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