11-Day Japan Itinerary in Autumn: Tokyo, Kyoto, Hakone and Osaka

I booked the first four days for Tokyo, based in an apartment-hotel in Shinjuku, the Citadines, with a kitchenette and washing machine—very comfortable traveling solo, around 140 € a night—. After a long flight, KLM via Amsterdam, what worked best for me against jet lag was not collapsing at seven: I forced myself to walk around Shinjuku and have yakitori for dinner in the alleys of Omoide Yokocho, and I stayed awake until a reasonable hour.

I split the following days between the classic and the modern. I woke up early for the Sensō-ji in Asakusa before eight, just before the tour buses arrived, and in the afternoon I let myself drift through the immersive art of teamLab Planets, with a time-slot reservation that's worth booking in advance. Another afternoon I spent between electronics and curry in Akihabara. And while I was at it, I signed up for a small-group sushi class in Asakusa: one of the things I laughed the hardest about on the trip and, as a bonus, a memory I took home in my hands.

I made the transfer to Kyoto on the shinkansen (the Hikari, about 2 hours 40 minutes). I sat on the right in case Mount Fuji appeared, and I got lucky with the sky: there it was, peeking through the window for a couple of minutes. In Kyoto the trip shifted gears: I slept in a traditional ryokan in Higashiyama, a tatami room and streets preserved like Sannenzaka just a step away for sunset.

I enjoyed Kyoto by waking up early; there's no other way. The Kiyomizu-dera opens at six and by seven there were already people, so the golden light on the main pavilion cost me an early alarm that was well worth it. I walked the Philosopher's Path all the way to Ginkaku-ji, stringing together streams, red maples and zen cafés, and I spent a morning in the bamboo forest of Arashiyama combined with the scenic Sagano train. I arrived before nine to take the photo without crowds; a little later the place fills up.

As I had a spare day in Kyoto, I escaped to Nara, about 45 minutes by train, and it turned out to be a great excursion: deer roaming free throughout the city, the enormous Daibutsu of Tōdai-ji and the lanterns of Kasuga-taisha. A warning I learned the hard way: as soon as the deer see you have cookies to feed them (shika senbei), they become very insistent and nibble at your clothes to get you to let go of the food. Also, the cookies stain, so bring a tissue handy.

In the plan I made, this day was marked as optional on purpose, and I was glad I left it that way: it's exactly the kind of day you prefer to decide on the fly, depending on how your body is holding up with the pace of the previous days.

Before Osaka I reserved one night to unwind in Hakone, a mountain hot springs area. The logistics became much simpler with the Hakone Free Pass, which covers bus, cable car, ropeway, the Lake Ashi boat and the train, all with a single ticket.

What I really went there for was the ryokan with onsen: thermal bath and kaiseki dinner with many small courses included. It was the night the trip downshifted a gear, and with clear skies Mount Fuji peeked out in the background. If I had to pick one moment of calm from the trip, it was that one.

I dedicated the final leg to Osaka, the city for eating in the street. Dotonbori at night is a festival of takoyaki, okonomiyaki and kushikatsu—lots of people, lots of neon—and after the calm of Hakone, the contrast did me good. The next morning Osaka Castle Park, beautiful in autumn, balanced out the plan.

From Osaka I returned to Tokyo on the shinkansen to catch my flight home. With the 7-day JR Pass activated on time—the day of the first bullet train, not before—all these intercity journeys were covered.

The backbone of my transport was the 7-day JR Pass, which I activated just as I caught the first shinkansen, because the beginning of the trip is done on local transport and I would have wasted days. For day-to-day travel I carried a digital IC card (Suica/Pasmo) on my phone, which saved me queues and worked for the metro, 24-hour shops (konbini) and vending machines.

Two more things that removed friction: an eSIM with data for the whole trip, which I activated on landing, and good travel insurance with coverage outside Schengen. And a jet-lag tip that worked for me: on the first day, natural light in the afternoon, a light dinner and bed at a decent hour.