Episode #163. I Know Because I Go: Why Japan Doesn't Work Without a Plan
OPENING
Welcome back to another episode of Jet Setting with Me. It's me, Michele, your friendly wanderlust instigator.
I am recording this episode from somewhere in the Pacific Ocean, which is a sentence I genuinely never thought I'd say. I am currently on a cruise through Japan — yes, Japan — and I have approximately a thousand things to tell you. But those episodes are coming. Today I want to talk about something different. Today I want to talk about what it actually takes to do a trip like this well.
Because here's the thing about Japan. It is not a destination you can Google your way through. I say that as someone who tried — and as someone who, about two weeks in to the planning process, handed the details over to professionals and watched the entire trip transform. Japan rewards preparation in a way that very few destinations do. And it punishes the lack of it in ways that are quiet, subtle, and completely avoidable.
I know this not because I read about it. I know this because I go.
So today, instead of the interview format I originally planned for this episode, I'm going to tell you five experiences from this trip that happened because someone made a phone call, built a relationship, or simply knew something the internet doesn't. And I'm going to tell you about two moments where I watched — right in front of me — what happens when none of that exists.
Let's get into it.
THE THESIS: HIROME MARKET, KOCHI
We were in Kochi — a port city on the island of Shikoku that most people on our ship had never heard of before they booked this cruise, myself included. Our guide, Kay San, had taken us to Hirome Market for lunch. Hirome is a covered market, air-conditioned, alive with local vendors and the kind of organized, beautiful chaos that makes a place feel genuinely of somewhere. Kay San walked us through it, found us seating — which is not a small thing in a popular market — recommended what to order, and helped us navigate the whole experience. We had katsuo no tataki, the local specialty — bonito tuna, seared, served with garlic and ginger, prepared right in front of us. We had a fluffy omelet. We had a chicken skewer. We had, yes, French fries, because sometimes you're in Japan and you want French fries and life is short.
And then two large tour buses from our ship pulled up outside.
Passengers streamed in — no guide, no context, no one to tell them what they were looking at or what to order or where to sit. Two of them ended up at the table right next to us. They looked at the menu. They looked at us. And they asked for help.
We became their travel advisors for lunch.
They were lovely people. They were also navigating one of the most sensory-rich markets in southern Japan with nothing but a phone and good intentions. The difference between their experience and ours wasn't luck. It was a phone call made months earlier to someone who had been there before.
That moment is what this episode is about.
#1: THE SAKE BREWERY
Kochi has nineteen sake breweries. Most of them are closed to the public — the process is closely guarded, the spaces are working facilities, and the families who run them have been doing so for generations with no particular need for outside visitors.
We toured one anyway.
It is the fourth of those nineteen breweries, and its current owner is the fifteenth generation of his family to run it. Fifteen generations. I want you to sit with that number for a moment.
Here's how it happened. Our guide Kay San — who had been arranged through a private shore excursion company I work with for all of our tours — heard me mention over lunch how meaningful a sake brewery visit would be. While we were eating, she stepped away and made a phone call. I don't know exactly what she said. I don't know who she knew or what favor she called in. What I know is that by the time we finished our katsuo, we had access.
The tour was given by the brewer's wife, who walked us through the entire operation with warmth and obvious pride. They were two weeks from harvest — the rice hadn't arrived yet, so the brewery was in a quiet waiting period, no smell, no activity, just the space and the history and a woman whose family has been doing this since before the United States existed. We tasted four sakes and two sake-based liquors. Each one is distinct. Each one earned.
Nobody else from our ship was anywhere near us.
Kay San is getting the most enthusiastic review I have ever written. And that experience exists because of a phone call made by someone who understood that what I wanted mattered — and who had the relationships to make it happen.
You cannot book that on Expedia.
#2: THE SUMO STABLE
I want to tell you about a young wrestler.
We were at Ise-No-Umi-Beya — one of 45 active sumo stables in Japan, with 250 years of history behind it. We had arrived at 8 AM with a private guide arranged through Wahbunka, a luxury Japan provider, which gave us a full half hour before practice began to learn everything: the ranking system, the tournament schedule, what these wrestlers earn, and what their daily lives look like. By the time we walked inside, we weren't tourists. We were informed, spectators.
And then you have to be quiet. Shoes off. Seated cross-legged on traditional Japanese mats. No stretching your feet toward the ring — that's considered disrespectful. No talking for the duration. About 24 of us were packed together with nowhere to go for 90 minutes.
Our guide came prepared with a dry-erase board and a pen so we could ask questions in silence and she could translate what the coaches were saying in real time. That one small detail changed everything about the experience.
During practice, a young, slender wrestler — visibly less experienced than the others — was paired with a higher division wrestler and put through an intense, grueling extra warm-up. The coach stood over him. Keep your head down. Keep pushing. When it was over, the young wrestler turned and said thank you. Not to the crowd. To the wrestler who had just worked him harder than he probably wanted to be worked. It was a little bit sad and completely beautiful — a quiet acknowledgment that being pushed is a form of respect.
Nothing about it felt like television. Nothing about it felt like a tourist experience. It felt like being trusted with something real.
After practice, the wrestlers do a cool down and open the floor for photos. Which, yes, we absolutely did.
This experience exists because a luxury travel provider had the access and the relationships to get us inside a 250-year-old sumo stable on a Tuesday morning. That is not something you find on a search engine.
#3: THE MAIKO
In Kyoto, we attended a private Geisha show — intimate, carefully arranged — where a Maiko, a Geisha in training, danced for us, taught us a traditional drinking game played entirely without alcohol, and then sat with us through a translator to share her world.
She doesn't own a smartphone. Geisha cannot. The tea house asked us not to post any photos with her on social media.
And here is what I want to tell you about that request: it was a gift. It meant I put my phone down and simply watched. No filming, no framing, no optimizing for anyone's feed. Just a young woman in an extraordinary life, sharing an afternoon with a small group of strangers who had been given the privilege of being present for it.
She told us how her kimono changes with each season. She explained that Maiko only have their hair done once a week and sleep in a specific position to preserve it. The sleeves of her kimono were long — they shorten as she grows older and advances in her training. On the back of her kimono was the symbol of the tea house where she lives and works and eats and sleeps alongside the other women of her house.
This was not a performance designed for tourists. It was access — real, considered, meaningful access — to a tradition that is quietly disappearing. The kind of experience that requires relationships, trust, and the kind of planning that doesn't happen overnight.
#4: FUSHIMI INARI — CONTEXT IS EVERYTHING
You've seen the photographs. Thousands of vermillion torii gates climbing a hillside in close, dramatic succession. It is one of the most photographed sites in Japan and it earns every image.
What the photographs don't tell you is what you're actually looking at.
Our guide, Shoya — arranged through the same private shore excursion company behind every exceptional experience on this trip — walked us through the Shinto way of prayer before we approached the shrine: two bows, two claps, and one final bow with a prayer and a wish. Two, two, one. We did the full sequence before the fortune-telling. Simple, deliberate, and surprisingly moving when you're standing in front of it.
Then a blessing ceremony unfolded that I was completely unprepared for. Led almost entirely by women — drums, a long harp, a single male flutist — and then a priestess performing a traditional Japanese dance to dust the visitors with prayers. No photographs allowed. There is a guard who watches the crowd to enforce it. Which meant that for once, everyone was simply present.
I got my fortune told. The bad luck fortunes get tied to a post at the shrine — you leave them behind. I took mine home. Highest luck category. Mr. Jet Setting came home with the level just below mine, which I will not be letting go of anytime soon.
#5 NARA — SOMETIMES THE RESEARCH IS YOU
I want to pause here and tell you something that might surprise you, coming from a travel advisor.
Not every extraordinary experience on this trip came from a provider relationship or a phone call made on my behalf. One of them came from homework. My own homework.
Nara was on my list from the beginning — the ancient capital of Japan, home to hundreds of freely roaming deer who have been considered sacred messengers for over a thousand years. I knew I wanted to go early, before the crowds arrived, and I knew I wanted the right guide for it. So I researched. I found Mo, an American-born guide who was raised in Japan and knows its history with the kind of depth that only comes from a life actually lived inside a culture. I booked her directly through a separate tour operator. And we arrived at the park early enough that our entire group was just us — our family and one other person.
What followed was one of the most purely joyful mornings of this entire trip.
The deer at Nara are not shy. The moment they sense you have the special cookies sold at the park entrance, they descend — and descended is the right word. They are overwhelming in the best possible way. It is fawn season, which means baby Bambi-sized deer were woven through the crowd alongside the adults. The females were curious. The males were committed. Mr. Jet Setting, who had announced with great confidence that he would not be feeding the deer, fed the deer. More than once.
And yes — they bow. You bow to them, they bow back. I had seen it on video and thought it was charming. In person, it is absolutely, completely, stop-you-in-your-tracks adorable.
Mo walked us through two temples before we reached the deer park — at each one, the ritual was the same: toss a coin, ring the bell, and pray with a namaste pose. One temple uses long, string words for its prayers. One uses short words in repetition. The distinction matters, and Mo explained why.
Then we visited Tōdai-ji — home to the largest Buddha in Japan. The scale of it is something photographs genuinely cannot prepare you for. You walk through the gate, and it simply stops you.
By the time the large tour groups began arriving, we were already done. Already fed. Already bowed at by deer. Already standing quietly in front of one of the great spiritual landmarks of the ancient world.
That happened because I did the research. Because I found the right guide. Because I made intentional choices before I ever got on the plane.
Which is, of course, exactly what I ask my clients to trust me to do for them.
Whether it's your travel advisor doing the work or you doing it yourself, the work has to happen before you land. Nara reminded me of that. And Mo made sure we experienced it the way it deserved.
#6: KAKIMOTO ARMS
This one is a little different, because I found it myself — on Instagram, which feels appropriately modern. But I want to include it because it illustrates something important: even the things you discover on your own land are better when the rest of your trip is handled.
I have a blowout membership at home. I get a blowout in every city I visit — it's a whole system, and I stand by it completely. When I saw a Japanese hair spa treatment on Instagram before the trip, I knew immediately I had to try it. I booked Kakimoto Arms in Ginza myself, showed up solo, and spent 70 minutes experiencing what I can only describe as the best $125 I have ever spent on my hair. Possibly on anything.
It started with a scalp analysis — almost like an X-ray of my hair and scalp — and then a treatment customized specifically for what she found. Head and neck massage, a treatment that smelled genuinely wonderful, a rinse, and then a blowout and style that left me glowing. I learned that my scalp is dry and that I should apply a serum before heat. She didn't try to sell me a single thing. I had to ask what product she had used. It's called Sublimic. It cost $25 at the salon. The equivalent at home would run $70 or more.
I walked out of Kakimoto Arms Ginza looking and feeling like a different person.
Now — why is this in a planning episode? Because I had the time and mental space to find it, book it, and actually enjoy it, with everything else handled. When you're not burning energy trying to figure out logistics, navigate language barriers, or recover from a tour that didn't go as expected, you have room to discover the unexpected joys. That is what good planning actually gives you. Not just the big experiences. The space to find the small, perfect ones, too.
THE CLOSING MOMENT: THE BULLET TRAIN
Before I leave you today, I want to tell you about a family we met at our kimono rental experience in Kyoto.
We got there on the Shinkansen — the bullet train from Osaka. Fifteen minutes. It is one of the great small pleasures of being in Japan.
This family, who were also on our cruise, had taken a taxi. An hour each way. They didn't know the bullet train was an option. When we mentioned it, their faces did something I recognized immediately — that particular expression of why nobody tells us that.
We gave them better options for the return. They were grateful. They were also out for two hours of their day in one of the world's most beautiful cities.
That information — fifteen minutes versus sixty, and significantly less expensive — is the kind of thing a travel advisor tells you before you get in the cab. It is not dramatic. It is not a once-in-a-lifetime moment. It is simply someone who has done the work, knows something you don't yet know, and makes sure you have it before it matters.
That is what this job is. That is what this trip has reminded me, over and over, in sake breweries and sumo stables and tea ceremonies and markets where tour buses pull up, and passengers look around, wondering what to do next.
I know because I go.
SIGN-OFF
That's it for today's episode of Jet Setting with Me. The full Japan series is coming — Tokyo, Kyoto, Kochi, and everything still ahead — and I cannot wait to bring all of it to you.
Until next time, make every journey a memory worth savoring.
