Off The Beaten Path Japan: The Coolest Tokyo + Yamanashi Trip You’ve Never Heard Of
If you think you’ve “done Tokyo,” let me introduce you to a totally different trip. This is the kind of itinerary you do when you want Tokyo energy but also want to disappear into the mountains, kayak on a quiet forest pond, drink historic Japanese wine, sit on a terrace at almost two thousand meters, and go home feeling like you lived ten different travel lives in one week.
And the best part is that everything is close to Tokyo. Like, actually close. You do not need to fly or commit to a five-hour train ride. This whole adventure sits right around Tokyo and into Yamanashi, which has become one of my favorite underrated regions in Japan.
So here is exactly what we did each day and how you can recreate the same trip.
Day One: Tokyo’s Olympic Legacy Spots and Hidden Corners
*The stadium was renamed as the MUFG Stadium from Jan 1, 2026
We kicked off the trip with a very unexpected theme. Tokyo’s Olympic legacy. I honestly thought this would be super niche, but it ended up being so much cooler than I imagined.
Our first stop was Musashino Forest Park, where you can literally walk or bike along the same route used for the Olympic road cycling race. It is super open, calm, and the park just feels like a breath of fresh air even though you are so close to the city. Planes take off from the little airport next door, which somehow makes it feel even more surreal.
After that, we headed to the Japan Olympic Museum. I swear, this place is way more interactive and emotional than you would expect. There are little games, exhibits, and moments that make you appreciate everything that went into Tokyo 2020. Even if you are not a big sports person, it is genuinely fun and beautifully put together.
From there, we explored Shinjuku the way locals actually use it. The hidden underground passages, the department store basements that all smell like perfectly packaged pastries and fresh cut fruit, and Hanazono Shrine tucked right inside the city noise but somehow still peaceful.
And on the very last day of the trip, we explored even more of Tokyo’s newest areas. Azabudai Hills, which feels like a futuristic green neighborhood, Takanawa Gateway City, which is basically Tokyo’s version of a future life test site, Dogenzaka Dori in Shibuya, which is full of shops and cafés, plus Shibuya Center Street for the classic chaos. We also saw Shibuya AXSH, which connects Shibuya with Aoyama in a really cool way.
Tokyo is changing constantly and honestly, there is so much to see that people skip because it is not on the top ten tourist list. This day alone made me want to come back and do a whole “new Tokyo” series.
Day Two: A Wellness Escape Into Yamanashi
The next morning we left Tokyo and drove toward Hokuto in Yamanashi. The second you leave the city the whole world changes. Mountains everywhere. Blue skies. Zero crowds. Such a vibe shift.
On the way out of Tokyo we passed the MUFG Stadium area again which is kind of wild because it was such a huge part of the Olympics and now it is just part of life here. Then we made our way to Moegi Village, which might be one of the most peaceful places I have ever seen.
We kayaked on a quiet forest pond surrounded by Yatsugatake. The water was still, the trees were glowing, and it felt like meditation. Truly the kind of activity you do once and immediately want to redo the next day.
For lunch, we went to ROCK, which is famous for its beef curry. It has been around for over fifty years and honestly, the hype is real. It is rich, cozy, and exactly what you want after kayaking.
Then we took the lift up to Kiyosato Terrace, which sits around 1,900 meters up. The views are insane. You see Mt. Fuji, the Southern Alps, and basically the entire world stretching out below you. The sky is such a bright blue that locals literally call it Yatsugatake Blue. It is definitely one of my new favorite viewpoints in Japan.
We ended the afternoon walking to Doryu Falls which has this super elegant flow that looks like silk running down the rock. It is quick to get to and completely worth it if you want a quiet waterfall moment.
We checked into Grand Mercure Yatsugatake Resort and Spa for dinner and had the calmest night. The whole day just felt like a wellness reset.
Day Three: Valleys, Wineries, Scenic Roads Back To Tokyo
Our last full day in Yamanashi took us even deeper into the mountains.
We started at Ojiragawa Valley where the water is this wild emerald color that looks edited. It comes straight from the Southern Alps and you can walk along the stream, hop over rocks, and just breathe in that cold mountain air. It feels untouched in the best way.
Then we visited Fumotto, which is a base-camp style complex at the foot of the mountains. It is filled with little shops, outdoor areas, local food, and a whole community vibe. Such a cool surprise spot.
After that, we went to Lumiere Winery, which has been making wine for almost 140 years. They still use Japan’s first European-style stone fermentation tank and walking inside honestly feels like entering a different era. If you like wine or even just history, it is such an interesting stop.
From there, we drove back to Tokyo, checked into our hotel in Roppongi, grabbed dinner and soaked in the city lights again. It is so crazy that you can go from mountains and wineries to Tokyo nightlife in the same day.
Why You Should Add This Route To Your Japan Trip
Most people stick to Tokyo, Kyoto, Osaka. And those are all great. But Japan’s magic is also in the places just outside the cities, where things feel slower and more local and unbelievably beautiful.
Yamanashi is close enough to Tokyo that you can visit without rearranging your whole itinerary. And once you get there, you get nature, culture, history, great food, and views that feel like they belong in a movie.
If you want something different from the usual Japan trip, something that feels special and refreshing, this is it. I cannot recommend it enough.
If you’re interested in a full 10-Day Japan Itinerary Guide, click here - it’s got tons of resources, places to visit and links.
And if you’re looking for more off-the-beaten-path experiences in Japan, make sure you check out my Kyoto Hidden Gems Guide for a detailed itinerary and map of locations that are ACTUALLY off the beaten path.
Got any questions? Send me a DM on @raimeetravel!