Planning Japan with me: a week for three

The first step is always a free fifteen-minute call. You tell me what you have in mind, I tell you what the planning fee would be, and we both find out whether I’m the right person for the trip.

This family came in with a clear brief:

• Art, local craft, great food and street food, strange architecture, makers’ markets and good bookstores
• One big thing a day, then an easy afternoon
• Most of the week in Kanazawa, with enough of Tokyo to say they’d been
• One room for the three of them if possible, and no packing up and moving every day

Their list of places included Myoryuji (the ninja temple), a hands-on cooking class, the 21st Century Museum of Contemporary Art and the Omicho Market.

If you go ahead, you sign my traveler agreement and pay the planning fee, and then I send you a questionnaire about how you like to travel. For this family that covered the things that shape a Japan trip: how many rooms, how much guiding they wanted, and what they eat.

Then I go looking for the options that actually match what you asked for, which usually means asking around.

For this trip I reached out to five companies that specialize in Japan.

Three of them couldn’t take it. Two have minimum spends, $25,000 at one and $30,000 at the other. The third had stopped taking requests for late September to mid-November because its guides were fully booked. October is high season in Japan, and the people who do this full time were already booked up.

The other two sent proposals, and both were good.

These were quoted in August 2026 for travel in late October 2026, for all three of them. Rates change, so treat them as dated examples rather than prices. None of the three includes flights to Japan, which the family booked themselves.

Two good proposals, and neither one was quite them. I’m always happy to talk more, so we had another call, and that’s where the family set their own budget for the week.

That changed the brief:

• Tokyo came off the plan entirely. They wanted those days for wandering and shopping.
• The gold leaf and wood charring classes came out.
• Green Car rather than Gran Class. They’d priced the difference themselves.
• In Kanazawa they wanted a city tour (small group was fine), the samurai district, a market tour with a cooking class, and something hands-on.

So I set both proposals aside and rebuilt the week from scratch.

Building it myself meant checking every piece of it, with help from the people I work with on the ground.

• The Kanazawa Marathon is on October 25. It’s the one day of the year you can’t get around Kanazawa, so they took the train up on the 26th.
• The late train back. I moved their Thursday train to Tokyo to 5:57pm, which turned a travel morning into a whole extra day in Kanazawa.
• The ninja temple only takes reservations from a month before your visit. It’s not something you can lock in early.
• Things sold out. The ring class I first found was full for their dates, so I found another. The morning city tour sold out, so they took the afternoon one. The market tour and the cooking class both sold out, and a private food tour with a local guide took their place.
• Rooms for three are hard. A lot of the cheaper rooms were twins, and real triples were scarce. I’d rather put the money into a room where everyone gets a real bed than put someone on a rollaway for six nights.
• One thing I couldn’t book from here. The private hot spring at the farmhouse has to be booked once you’re in Japan, so it’s in their itinerary for them to book when they arrive.

Their own numbers for the week, for the activities, getting around and the hotels, added up to about $3,100 to $3,400. The version they booked came to about $4,200 before flights and rail. The activities came in under what they set. The rooms didn’t, because real rooms for three cost more than twins, and I told them that before they said yes.

It came in under both proposals: about $14,200 less than the private version and about $7,800 less than the full-service one. Most of that gap is how much of the week is private, and how much of it is planned at all.

After they approved the proposal, I booked the hotels, the transfers and every activity. About ten days before they flew, they got their final itinerary, which they can download to their phones and use offline.

If you’ve been thinking about Japan and don’t know where to start, that’s exactly what the call is for. You don’t need dates or a city picked yet. Just bring your hopes and dreams for the trip!

My Japan page has where I’d start, season by season. If you’re planning as a couple, my post on Japan for queer couples covers the law and the norms. If you’d rather write first, send me your trip and I’ll start looking.