By Christina Kawamoto-Butler | CKB Travel
Somewhere between the rainbow grilled cheese and the last-minute Uggs purchase, I realized that Harajuku and Shibuya weren’t just TikTok-famous destinations—they were a snapshot of what made this trip so special: surprises, soft moments, and our family exploring a world completely different from our own.
Here’s what our day looked like—and what I’d tell anyone heading to these iconic Tokyo neighborhoods with kids, cash-only snack stands, and a slight case of jet lag.
Getting There: A Little Confidence and a Lot of Growth
By the time we took the train to Harajuku Station, we felt like pros. After navigating the route from Shinagawa like seasoned commuters, Alyssa had fully claimed her title as navigator, leading us smoothly to the Yamanote Line. I didn’t even panic this time.
We stepped off into grey skies and drizzle, but the weather matched the vibe—soft, cozy, and perfect for a day of exploring.
Takeshita Street: Viral Snacks & Kawaii Overload
Our first stop: Takeshita Street—a sensory explosion of pink signs, themed stores, and food stands with snacks we’d only seen in videos.
• Strawberry cream crepes were our first hit—sweet, light, and gone in 60 seconds.
• Tanghulu grapes and strawberries followed (because the girls are officially obsessed).
• Then came the rainbow grilled cheese, which Keao stole from my hands with wide eyes. That moment felt like a turning point. Food has been a struggle for her, but she took a bite—and loved it.
Totti Candy Factory came through with no lines and the iconic rainbow fluff.
Honestly? Takeshita Street was calm. I expected crowds, but we were able to walk freely, stop often, and enjoy without the chaos I’d feared.
Lunch Detour: From Viral Udon to Quiet Ramen Shop
We attempted the viral carbonara udon spot Menchirashi, but the line was 40 deep before it opened. Hard pass.
Instead, we stumbled on a ramen shop down a quiet alley. It had a vending machine outside to order, cash-only, and exactly what we needed: hot soup, crispy karaage chicken, fries, gyoza, and unlimited cold water. The vibe was perfect. Pat’s face said it all—this is what he came to Japan for.
Kiddy Land & Uggs (Yes, Really)
After lunch, I took Keao to Kiddy Land, a four-story paradise of Japanese character merch. She picked out some Kirby, Kuromi, and a new anime doll—and watching her light up made my heart so full. I could’ve stayed there all day.
Then Alyssa asked if we could stop at the Ugg store. I wasn’t planning to blow the budget, but $120 for shoes that cost $200+ back home felt like a good deal. And these weren’t just shoes—they were souvenirs that she and Mele would wear for years, reminding them of this day.
Cat Street to Shibuya: Slowing Down in the Rain
We strolled down Cat Street, popping into cute boutiques, stopping at Lilly Cafe, and sipping matcha in a little upstairs coffee shop above a clothing store. It felt like a scene from a movie—rain falling, matcha warming our hands, and the city moving slowly around us.
By the time we got to Shibuya, we were fading fast. We skipped the Disney store (shocking, I know), passed by iconic shops, and finally stood at Shibuya Crossing—yes, that Shibuya Crossing.
Pat looked at the crowd and said, “Wait… we did all this to watch people cross the street?”
Yes. Yes, we did.
Because it’s not about the crossing—it’s about the fact that we made it. From a town with more cows than people to the heart of Tokyo, we crossed a different kind of line that day.
Watch our day at Harajuku and Shibuya
Final Thoughts: What I Learned Wandering Harajuku & Shibuya
1. Don’t force an itinerary—just explore. Our best meals and moments weren’t planned.
2. Cash is still king. Especially for street food.
3. Teen girls will shop—and it’s worth budgeting for it. Watching them get excited about Uggs and anime dolls? Priceless.
4. Rainy days can be cozy, not canceled. Tokyo still shines in the drizzle.
5. Give your kids space to try new things—but let it be on their terms. Keao’s rainbow cheese moment was everything.
This day wasn’t about landmarks or big moments. It was about the in-between—the soft steps, the smells of sweet crepes, the laugh over matcha, and the realization that we’re doing something amazing together.
Planning your own family adventure to Tokyo? Want help with itineraries that leave room for discovery (and dessert)? I’ve got you.
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