Japan Report 3: The Final Installment

Ohayō Friends,

We've reached the final chapter of the Japan Adventure Trilogy.

I’m writing this from home, jet-lagged but happy, with my suitcase still half-unpacked and my nervous system slowly recalibrating. This last newsletter is about Kyoto and Osaka, which ended up being a study in contrast so stark that it almost felt like whiplash.

The two could truly could not be more different...

Kyoto is quiet, traditional and serene. The lighting is dim. Everything is in earth tones. The food is traditional. The people are deeply respectful. The fashion is understated. Osaka, on the other hand, feels like a bomb of neon blew up in a carnival and exploded into food stalls, loud music, street art, and colorful characters from all over the globe... Every taste, smell, and sound imaginable.

Both cities are incredible. But damn are they different.

Kyoto's gorgeous Park Hyatt Hotel (I could afford a cocktail, not a stay here 😂)

Kyoto: A Study in Ritual

Now that the trip is complete, I can honestly say that Kyoto was my favorite stop.

I know some people—even some of my travel partners—said there were moments where they didn’t feel particularly welcome in Kyoto. It has a reputation for being less warm and accessible to Westerners. But while I did see less menus available in English, and more “rules” regarding daily life, I never felt unwelcome. In fact, what I loved most was that it felt like the most authentic peek into Japanese culture that we had on this trip.

I loved how small, peaceful and nature-oriented it is. You can walk from one side of the city to the other in under an hour. There are neatly-trimmed trees shading every sidewalk, little canals winding through neighborhoods, and elegant homes folded into the mountains.

After the wild intensity of Tokyo and the frozen tundra of Hokkaido, Kyoto felt like an oasis of zen and beauty.

The Gion district—the historic geisha neighborhood—was one of the most beautiful places I’ve ever been. Narrow lamplight-lined streets hugging calm canals, traditional Edo-era architecture with sliding walls and sloped roofs straight out of the samurai era. Everything feels intentional and curated, with no trash in sight and secret pockets of beauty everywhere.

Take for example: the Le Labo store that has a secret garden (pictured above) with matcha bar tucked inside—something you’d never know just walking by. Everything in Kyoto feels carved from stone or wood and then accentuated with tasteful flora and fauna. It is a masterclass in minimal design!

We had not one, but two traditional kaiseki meals in Kyoto, which are hyper-traditional, formal, and deeply ritualized. You are greeted and served by women in traditional dress, who ask you to remove your shoes in order to enter the dwelling–usually old traditional homes. You don slippers to walk to your private dining room, then remove your slippers to enter the sliding doors, and eat in socks at low tables on tatami mats.

One course of a kaiseki dinner

The food itself is incredibly wholesome and restrained… lots of root vegetables and mushrooms–often pickled or carved into flowers, sometimes threaded onto grasses, and always arranged like tiny works of art. There is plenty of seafood, various broths and exotic fruit for dessert. The plates are lacquered wood, hand-painted with birds and flowers. Each course is served with reverence and solemnity.

It’s definitely not how you’d want to eat every day, but it gave me a totally new appreciation for how different cultures express fine dining.

We also made a pilgrimage to Fushimi Inari, the iconic “gates,” just outside Kyoto. Though it’s only ten minutes away by subway, it feels like a different world. Thousands of orange torii gates wind up Mount Inari, originally erected as offerings for bountiful harvests. (Today, many are prayers for business prosperity).

Little statues of foxes—kitsune—are everywhere on the mountain, holding wheat in their mouths and wearing bright neckerchiefs that are clearly changed out regularly by locals with care. Even though it was touristy, it was magical. It even snowed while we were there! 

Osaka: Chaos, Incarnate

Then came Osaka.

Osaka is the only place in Japan where we saw street buskers and cigarette butts, heard loud music, and people yelling. The first time we heard shouting, we genuinely thought something dangerous was happening, because Japan overall had been so quiet and polite. 

But no. It was just kids having fun in the subway station. Because that’s allowed here.

Dotonbori, the beating heart of Osaka

Historically, Osaka was a port city built by merchants—working class, commercial, pragmatic—very different from Kyoto’s feudal lords and imperial traditions. And you feel that immediately. The intense sense of propriety that permeates much of Japan loosens its grip here… to the point that it almost loses control. 

Where Kyoto is formal and hushed, Osaka is loud, chaotic, and joyful. It reminded me a lot of New York City. We saw the most diversity here of anywhere in the country… every language spoken, cuisine imaginable, and form of self-expression.

That contrast shows up in the architecture too. When we arrived, the wide boulevards and stately buildings actually reminded us of Chicago (go figure!). And then—within two blocks—you’d find yourself in a maze of alleys with doner kebabs, two-for-one whiskey shots, vintage clothing, and tiny bars hidden behind unmarked doors.

Dotonbori, the area you see in all the photos, is pure sensory overload. Much like Times Square, but the Japanese version… Giant crabs, dragons, samurai warriors bursting off buildings. Flashing lights and sounds everywhere. We even went to their version of conveyor belt sushi (because we spent all our money on kaiseki meals in Kyoto), complete with huge LED touchscreens where you order and watch food and cocktails zip straight to your table.

It was wild and fun. And honestly exhausting.

Some of my favorite moments were in tiny alleyway bars that we would stumble upon based on handpainted signs merely stating "BAR." The city seems to be full of them. They offer a small (think: less than 10 seats) escape from the madness and a fascinating peek into the personality of the proprietors--many of whom are in their 70's and have owned their spots for 20+ years! You will not find craft cocktails... just whiskey highballs, highly eclectic decor and burned CD’s playing oldies.

Fanny Mae, for example, is a Rolling Stones themed bar run by the legendary Masato and filled floor to ceiling with vintage posters, artwork and vinyl albums of the legendary rock band.

Oh and fun fact: in Japan you can’t smoke outside, but you can smoke inside most bars. So prepare yourself for that!

Masato-san, legendary owner of Fanny Mae

A Final Reflection

What struck me most was how divided our group was on our favorite stops of the trip. For some, Tokyo was the end all, be all. For others, Osaka was hands-down the best. We all had a blast visiting Sapporo. And for me, Kyoto stole my heart.

I think timing mattered too. By days 11, 12, and 13 of a two-week trip, I was tired and overstimulated, and Kyoto gave me exactly what I needed: calm, beauty, quiet. Being thrown back into Osaka’s chaos at the very end felt like a lot. If I were to do it again, I might flip the order: Osaka while I had the energy for it, then save Kyoto for last as a peaceful exhale before heading home.

One thing is for sure: Japan truly has something for everyone!

So many of you have asked for specific places we went, so I’m working on a city-specific guide of the top 5 things I did in each place…. Wine and non-wine related. I’ll get that to you all next week.

It’s been a wild and eye-opening couple of weeks. I’m grateful beyond words for the privilege of being able to explore new corners of the globe. And I’m also very excited to be home.

Kanpai and thanks for coming along on the adventure,
Kelsey