September 22, 2026
Jordan Brady, Founder
I’ve been planning Japan ski trips for years. And after this trip — skiing new terrain, checking out new luxury hotels, navigating the transfers between new regions, and eating my way through all sorts of restaurants — I’d plan them a little differently.
Not completely differently. But there are a few decisions I’d make with much more confidence now, and a few things I’d stop recommending entirely. Here’s the honest version.
Decision I’d Change
I’d stop recommending a single overnight in Lake Shikotsu as a part of a Hokkaido-based itinerary. We love incorporating a high-end ryokan stay in Lake Shikotsu to break up a Hokkaido-based ski trip, and usually we recommend one night. But by the time you get there, it’s typically late afternoon or early evening and the sun is starting to set.
In order to really embrace and enjoy this experience, you need a solid two nights. Time to check in, scope out the property (and your room), soak in your private onsen, and enjoy the coursed out Kaiseki dinner (and maybe a Japanese whiskey by the fire after dinner).
With only one night and a 10am transfer to catch to your next destination, you also want to enjoy breakfast, take another soak in your private onsen for maximum recovery, peruse the local gift shop, and walk around the lake. There is simply not enough time for all of this. You really need two nights to take full advantage of all the ryokan has to offer and soak in the beauty of Lake Shikotsu, without feeling rushed.
Decision I’d Keep
There is a guide we request by name anytime we have clients in Tokyo. He is from the UK but has called Japan his home for many years. Spending an afternoon with him going completely off the beaten path and learning about the cultural or historical relevance of whatever it was we were interested in about Japan was incredibly rewarding. The guy is an encyclopedia, an open book, and he knows how to deliver it in an engaging way, with flair.
Ending the tour with a relaxing dinner and drinks with him at an izakaya we would have never found ourselves, with no English menus, no English-speaking staff, and being the only Westerners in such a buzzing restaurant, was something we will never forget. There are many clients who express interest in exploring Tokyo on their own. But everyone must have some time with this man or someone on his team! They just do it differently, and you are guaranteed to feel more connected to Japanese culture…
Decision I’d Make Sooner
Book dining reservations, but don’t stress about having a reservation each night. Restaurants are a big stress point for Japan ski trips (especially for larger groups headed to Niseko or the Hakuba Valley during peak powder season). It is important to get some core dining reservations on the books, and get in early to get your pick. But it is also ok to have a couple nights free without a reservation. This will allow you to wander and hit up one (or more) food trucks, or pop into an izakaya that only takes walk-ins. And of course, if all else fails, there’s always a 7-Eleven or Lawson, where you can have an insanely high quality convenience store meal for a fraction of the price!! It’s all a part of the Japan ski experience.
Where I’d Tell Clients To Spend Vs. Save
Spend On: The luxury hotel with a great onsite onsen. Bonus if it has a cold plunge, sauna, and steam room to complete the recovery circuit. Daily recovery over the course of a hard powder skiing trip is crucial. And there is something uniquely special about the way you feel after hitting a Japanese onsen every day after skiing. Euphoria! Must be the minerals…
Save on: Lunch – Whether you’re on the mountain or in the city, you can indulge in some of the best flavors of your life at the casual ramen, katsu, or sushi joint for less than half the price of the more formal spots.
Skip entirely: Shipping your skis. Clients ask about this all the time, and unless you are 100% married to your specific ski setup, you’re better off saving the lug, bringing your boots, and renting your skis or snowboard there. We always recommend the premium rental package that allows for unlimited gear swapping in case conditions change or you want to try something else. Shipping skis is also wildly expensive.
Ready to Start Planning Your Japan Adventure?
If Japan has been on your bucket list and the time finally feels right, get in touch with team@thejourneybound.com to start the conversation and begin planning your Japan adventure. Let’s schedule a time to talk through it. Or, if you are in the middle of planning your dream Japan ski trip but you feel stuck, we are happy to help.
