33 Days in Japan Across 2 Trips

I've been to Japan twice. The first trip was the route everyone takes. The second trip was the one I actually designed. Here's what changes after you've already done Tokyo, Kyoto, and Osaka—and what I'd tell a first-timer vs a repeat visitor.

I don't say this lightly. Japan is the most toddler-friendly country we've traveled in—and we've done 18 international trips across 6 continents.

Clean streets. Reliable trains that run to the second. Convenience stores on every block with kid-friendly snacks. Family restrooms in every station. A culture that's genuinely welcoming to small children—strangers will wave at Tristan, station attendants will help you with the stroller, and nobody gives you the look when he makes noise on the train.

The biggest challenge is the time zone: 13-14 hours from US East Coast. The jet lag hits hard in both directions. But once you're adjusted (give it 2-3 days), everything else is easier than traveling in Europe.

If you've never been to Japan, this is the trip. No shame in doing the classics—they're classics for a reason.

Tokyo (6 days)

Six days sounds like a lot. It's not enough. Tokyo is a collection of cities pretending to be one city. Shibuya, Shinjuku, Akihabara, Asakusa—each is a completely different experience. With a toddler, you'll cover less ground but that's fine. Pick 2-3 neighborhoods per day.

Nagoya (2 days)

Most people skip Nagoya. It's a transit city between Tokyo and Kyoto. But it has one of the best castle reconstructions in Japan and the food scene is underrated—miso katsu and hitsumabushi (eel) are worth the stop.

Nara (3 days)

Nara is where Tristan lost his mind over the deer. They bow. They eat from your hand. For a toddler, it's a petting zoo the size of a city. We spent 3 days here and could have done more. Base yourself here and day-trip to Kyoto—it's 45 minutes by train and way cheaper to stay in Nara.

Kyoto (2 days)

Kyoto is beautiful and overwhelming. Thousands of temples. Massive crowds. With a toddler, pick your spots: Fushimi Inari (go at 7am before the crowds), Arashiyama bamboo grove, one good garden. That's a full day. Don't try to see everything.

Osaka (3 days)

Osaka is where you eat. Dotonbori at night is sensory overload in the best way. Takoyaki, okonomiyaki, kushikatsu—everything is street-level and toddler-accessible (no stairs, no dress codes, food comes fast). This city has more personality than Tokyo and less pretension than Kyoto.

Hakone / Mt Fuji area (2 days)

If the weather cooperates, you see Fuji. If it doesn't, you see clouds. We got clouds. Still worth it for the hot springs (onsen) and the Hakone Ropeway. Just don't plan your trip around Fuji visibility—you'll be disappointed more often than not.

Two years later, we went back. This time I skipped the golden route entirely. No Kyoto temples. No Nara deer. No Hakone clouds. Instead:

Onomichi / Inland Sea (2 days)

Onomichi is a hillside town overlooking the Seto Inland Sea. It's connected to Shikoku by the Shimanami Kaido—a cycling bridge route across six islands. With a toddler we didn't cycle, but the town itself is full of narrow hill paths, cat shrines, and small temples with nobody in them. This is the Japan that Instagram doesn't show you.

Hiroshima (2 days)

Hiroshima changed how I think about travel. The Peace Memorial Park is heavy, but it's important. The city itself is modern, vibrant, and surprisingly fun—okonomiyaki Hiroshima-style is the best version. Day-trip to Miyajima Island for the floating torii gate.

Should you bring a toddler to the Peace Memorial Museum? We did. Tristan didn't understand it, but the park itself is peaceful and green. We sat by the river. It was quiet. That's enough.

Koyasan (1 day)

An overnight stay in a Buddhist temple on a mountain. They serve you shojin ryori (temple cuisine), you sleep on tatami, and at 6am you attend morning prayers. With a toddler this was ambitious. Tristan made it through about 8 minutes of prayers before we had to leave. Worth it anyway.

Nikko (1 day)

Day trip from Tokyo. Toshogu shrine is one of the most ornate things you'll ever see—covered in gold leaf, carvings, and color. It's the opposite of Kyoto's austere zen gardens. Tristan liked the monkeys (real ones, in the forest behind the shrine).

Kamakura (2 days)

The Great Buddha. Beach town energy. An hour from Tokyo by train. If you're staying in Tokyo for a while, Kamakura is the best day-trip or overnight—especially if you need a beach day to reset after temple fatigue.

Stroller on the Shinkansen

The bullet train has luggage space behind the last row of each car. Book the last-row seat online (you can on the JR site) and your stroller goes right behind you. No overhead bin wrestling.

Convenience Stores Are Your Kitchen

7-Eleven, Lawson, FamilyMart—these are not gas station junk food. They're legitimate meal sources. Onigiri (rice balls), egg sandwiches, hot soup, fresh fruit. For a toddler, this is a lifeline—fast, cheap, available at 3am when jet lag has everyone awake.

Cash Still Matters

Japan is more cash-dependent than you'd expect from a tech-forward country. Temples, small restaurants, and local shops often don't take cards. Carry 10,000-20,000 yen on you. 7-Eleven ATMs accept foreign cards—this is the only reliable ATM source.

Train Etiquette With a Toddler

Japanese trains are quiet. Your toddler won't be. People are more understanding than you'd think, but carry snacks and a tablet loaded with shows. Priority seating is respected—you'll get offered seats constantly.

Without question. Japan is one of those places where each trip feels like a different country. Trip 1 was tourist Japan—spectacular, efficient, overwhelming. Trip 2 was local Japan—quieter, deeper, more surprising.

If there's a trip 3, it would be Hokkaido in winter (Sapporo, ski resorts, ice festivals) or the southern islands (Kyushu, maybe Okinawa). Japan is deep enough that you could go ten times and still not repeat yourself.

For us, the question isn't whether to go back. It's which Japan to visit next.

Gear List (Full Links)

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• UPPAbaby Minu V2 Stroller
• Sony A6000 Body
• Sony 18-105mm f/4 Lens — OSS stabilization, great range
• GL.iNet Travel Router
• Stroller Travel Bag
• Stroller Organizer Bag

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