Tokyo was the perfect launchpad for our Japan adventure—equal parts peaceful and chaotic, traditional and wonderfully weird. Over four jam-packed days, we experienced centuries-old shrines, wild street fashion, micro pigs, futuristic art, a surprise Disney day, and so many moments that made us stop and say, “Wow, we’re really here.”
Home Base: Hyatt Regency Tokyo
We based ourselves at the Hyatt Regency Tokyo, located in the heart of Shinjuku and a perfect launchpad for exploring the city. One of the best perks? Starting each morning with the best breakfast of our entire trip—a full spread of both Japanese and Western options that fueled us for full days of adventure.
Another standout: the concierge team. Having someone readily available to assist with directions, call transportation, and even shuffle dinner reservations was a huge asset. In a country where English speakers are less common and special requests aren’t typically entertained (Japan is full of lovely rule-followers!), their help smoothed the way more than once.
We booked through Hyatt’s Prive program, which meant we also received extra perks like a $100 hotel credit and room upgrades when available. These kinds of added values really make a difference in a city like Tokyo.
Also—confession—we don’t have our own photos of the newly renovated, City View room because we were so exhausted after a long travel day that we collapsed the second we walked in. So yes, we’re borrowing the hotel’s website photos… and trust us, they’re accurate!
Tokyo Day 1: Rain, Reunions & Shibuya Chaos
We woke up in Tokyo ready to hit the ground running… or more like splashing. It rained most of the day, which somehow made the city feel even more alive. We met up with our friends Anna and Josh and their kids—who also happen to have identical twins! I’ve known Anna since childhood and met Josh nearly 20 years ago, which made wandering the streets of Tokyo together feel both surreal and full-circle.
We started with the serene Meiji Jingu Shrine—an oasis of calm before diving into the colorful madness of Takeshita Street which included a stop for some gachapon, a Japanese vending machine that dispenses small, plastic capsules containing collectible toys.
After a spin through Shibuya Crossing (umbrellas colliding in every direction), we grabbed lunch at a conveyor belt sushi spot and made a few more quirky stops on the way back to the hotel—like the 3D cat billboard and the Godzilla head peeking out from the Gracery Hotel. We ended the night with ramen in a tiny spot near Golden Gai. Day 1 was the perfect start to our trip!
Tokyo Day 2: Temples, Tiny Pigs & Ninja Training
Josh had to work, but we met up with Anna and the girls again (thank you, teacher workday timing). We started at the Asakusa Visitor Center for a rooftop view, then wandered Nakamise Shopping Street snacking our way toward Senso-ji, Tokyo’s oldest temple. Japan street food is the gift that keeps on giving. (Pro Tip: you should not walk and eat your street food treats in Japan – it is considered rude. You should stand off to the side – NOT in front of another business – to consume your food).
But the real highlight? A micro pig café. Yes, you read that right—a café full of tiny, snuggly pigs. We wrapped our time with friends with a scenic boat ride along the Sumida River, then regrouped at the hotel before heading to dinner at the Ninja Experience Café. We got to train like ninjas before dinner, and it was touristy in all the best ways.
Day 3: A Spontaneous Disney Detour
This was not part of the original itinerary… but we accomplished so much our first two days that we suddenly found ourselves with a free day, and I casually floated the idea of checking out Tokyo DisneySea. Cue: immediate YES from the boys. It turned out to be the perfect mix of fun and novelty. (And just for the record, I do love Disney—I just don’t plan Orlando trips. My heart belongs to international travel.)
Tokyo Day 4: Sumo Strength, Robot Servers & Barefoot Art
We kicked off the day with a visit to a sumo wrestling training facility, and watching these athletes in action was absolutely captivating. But I must admit, there was a lot of coaching beforehand to make sure the boys understood that sumo was nothing to laugh at!
Sumo in Japan isn’t just a sport. It’s tradition. Discipline. Ritual. You feel the power in every movement, but it’s the cultural richness of the experience that really stays with you. One of those “pinch me” moments that reminds us why we travel. My favorite shot of the day was watching two of the sumo wrestlers walk away from the practice ring towards the modernity of Tokyo – one still wearing his loincloth aka “mawash” in Japanese.
From there, we pivoted to something delightfully modern: lunch at a robot café. But this wasn’t just a novelty experience—the robots were operated remotely by people with disabilities working from their homes across Japan. It was such a meaningful, inclusive use of technology and a total hit with our crew.
Next up: teamLab Planets, an immersive digital art installation where we walked barefoot through glowing water and shifting rooms that felt like dreams come to life. We dried off in the Imperial Palace gardens, soaking in spring air and a rare moment of calm in the bustling city.
We ended the day with dinner and a catch-up with my friend Julia (in Japan with her mom!) at a fun restaurant where everything was served via a large wooden spatula, then karaoke with Anna and the girls, followed by a peek inside the U.S. Embassy compound, where their family spends much of their time. It was a fascinating glimpse into expat life.
Tokyo was everything we hoped—and didn’t expect—it to be. It challenged and delighted us in equal measure. And it reminded us how much richer travel can be when it includes connection: with friends, with culture, and with experiences you simply can’t plan online.
Next stop: Hakone for hot springs, mountain views, and a much-needed exhale. More on that in my next blog post.
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