A Journey Through Japan: Tokyo, Hakone, Kyoto, Osaka, and the Iya Valley on the Island of Shikoku

A YEAR AGO, I WAS GETTING READY to go on a life-changing trip to Japan with eight of my best friends. Traveling to Japan had been my dream ever since I was a kid.

I don’t know how we pulled it off, but I’ll always be grateful to have had a tribe to share in the experience of traveling to the other side of the globe. I’ll never forget this month we spent exploring, laughing, eating, and admiring one of the most remarkable countries in the world.

I wrote a series of stories right when I got home. However, making this video is something I’ve wanted to do for the last year. It makes me so happy to relive this trip and these memories; I love these guys more than anything.

We started in Tokyo and headed south, first stopping in the rural mountain town of Hakone at the base of Mt. Fuji. From there, we’d visit the ancient capitals of Kyoto and Osaka, two cities with incredibly distinct personalities.

From Osaka, we continued our adventure on the island of Shikoku to stay in a cabin owned and run by Shino-San, one of the funniest and most interesting men I’ve ever met.

To wrap it all up, we finished back in sprawling Tokyo for one final go.

Touching down in Tokyo on a cold and rainy night was surreal. It just felt like I’d imagined this moment for so long. It was the day before Thanksgiving, and we arrived on different flights as small units of two’s and three’s, depending on where we were coming. You can’t visit Japan and not visit Tokyo.

We spent a week there at the beginning of the trip, lost amongst its neon lights and back-alley ramen shops. We finished the journey in Tokyo as well; it only felt right.

If Tokyo was the only right way to start a trip to Japan, Hakone was the ideal second stop to experience the countryside that defines the nation. We took a train to Hakone, a town nestled under the shadow of Mt. Fuji.

We traversed the Old Tōkaidō Road, an ancient coastal highway used during the Edo Period (1600–1868). Hundreds of years ago, travelers would walk between the imperial cities of Kyoto and Edo, modern Tokyo, along this dangerous, natural route.

Kyoto is formal, serene, revered. It feels as if stepping through time into another era of light and beauty. Walking through Kyoto’s lantern-lit streets under the night sky is an otherworldly experience that will attune you to your senses. The night isn’t frightening; it’s as if your soul connects to it.

Osaka is boisterous, a port city known for its unbelievable staple street food dishes. We tried some of the best and well known: Izakaya Toyo for charcoal-grilled tuna cheek and mountains of uni, and Umai-ya, one of the oldest takoyaki (fried Octopus balls) stalls in Osaka.

The people we met, Toyo himself of Izakaya Toyo, and Mr. Kita of Umai-ya, truly made the experiences unforgettable. They are kind people who love what they do and live to connect with others; their goal is to make you happy through their gift of food and a warm smile.

Going to Japan requires taking a few days to get off the beaten path. There’s hardly anybody around in the small mountain villages; time moves slow, life is simple.

We encountered this serene way of life in the Iya Valley on the island of Shikoku, where we were hosted in a wood cabin by Shino-San. Shino-San waved to everyone as if he was the mayor and quickly became our friend.

It didn’t matter that we could barely understand each other; we all did our best and bonded through laughter.

This trip brought the absolute best out of me. It affirmed my dream not only to become a travel writer and content creator, but of becoming a citizen of the world.

The lessons you learn when traveling are indispensable. Through practice and discomfort, you connect with your inner self, the spirit that shines when free in the world to be.

No language barrier, no cranky grocery vendor, no bad weather can deter the spirit. When traveling, the spirit shines as its most authentic, sincere self.

Traveling evokes the good in people. When we travel, we’re acting as part of a global community. We wait for buses and trains, flights and ferries; our senses are on high alert.

In Japan, I witnessed genuinely kind people who went out of their way, sometimes drastically, to help us when we were lost or confused, which was pretty often.

The Japanese display of generosity encouraged me to strive to do the same. The people we met in Japan have remained in my heart, the tastes have stayed on the tip of my tongue, and the memories have made me who I am.

I know we’ll be back sooner than we can imagine. Still, visiting the inspiring country together as best friends at that time of our lives is something I’ll cherish for the rest of my life.

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