Travel Blog Series Part 3: Tokyo Days 3-5
Day 3
On our third morning in Tokyo, I kept up my running habit with a loop that hit a few iconic spots—Japan National Stadium, the outer grounds of the Imperial Palace, and Meiji Park. At Meiji, I accidentally stumbled upon some sort of official police ceremony. Dozens of battalions were lined up in formation, news crews were filming, and there I was, in running shorts, zipping past like a confused foreigner. It felt like I had my own personal cheer squad—but also like I was majorly interrupting and breaking some unwritten rule. And of course, with all that security, I couldn’t get away with jaywalking; every red light had to be honored, even if there wasn’t a car in sight.
The main event that day was the Tsukiji Outer Market, and I was so ready. My Instagram algorithm had clearly caught on to my travel plans, and I’d been fed a steady diet of reels showing “Top 10 Must-Try Foods at Tsukiji.” I came prepped, hungry, and armed with 10,000 yen in cash (thanks to my parents exchanging dollars before we left). Many stalls are still cash-only, so this was a strategic move.
If you’re planning a visit, go early in your trip while your tolerance for fish in the morning is most likely to be higher. Also, it closes at 2 p.m., and crowds pick up fast. I arrived around 10:30. Kayla got sidetracked by a shrine along the way, so I kicked things off solo with a pricey but delicious slice of fresh cantaloupe—Japan’s fancy fruit game is no joke.
When Kayla arrived, she graciously waited in line for a tuna sampler while I ran to the bathroom. The sampler included lean, medium-fatty, and extra-fatty tuna, and we both agreed the medium was the best. It came with rice mixed with wasabi and a little dixie cup of green tea—simple but amazing. Japan has a strong no-snacking-while-walking rule, so you eat right at the vendor and toss your trash in designated bins (people are serious about proper waste disposal here!).
Next came kushi-dango, a sweet soy-glazed grilled rice ball on a skewer. Warm, sticky, a little messy — one of my faves from the market. Then we tried a seafood dumpling skewer, but I clumsily dropped one. I strongly considered the five-second rule, but Kayla gave me the look, so I let it go. More room for the next snack.
Which... was a giant seafood cracker. Very Instagrammable, not very edible. We got the lobster one (it’s what everyone else was doing), but it was basically a flattened lobster — shell and all — pressed into a cracker with potato starch. Crunchy, chewy, and not in a good way. I couldn’t swallow parts of it and had to spit them out. Worth it for the photo, not for the flavor. We ended that tasting session on a high note with an iced matcha. Much needed palate cleanser.
From there, we walked to Ginza, Tokyo’s upscale shopping district. We split up for a little solo time—I hunted down a pastry and a jelly pouch made of konjac (texture like a Maurten gel, which I found refreshing, though it would’ve been better cold). Kayla, naturally, found another Uniqlo…and a friend from Vegas. Small world.
This was our last morning to ourselves before our parents arrived, and we felt a little sentimental. We'd landed in Tokyo three days earlier, figured things out on our own, and were proud of how quickly we adapted. We knew things would shift with our parents in the mix—not worse, just different.
Later that afternoon, we met up with our parents at Tokyo Station after navigating a bit of chaos. Our luggage had been stored at a drop-off point for the day, so it became our meeting spot. We collected our things and headed to Hilton Tokyo Bay, our hotel near Disneyland. The room was huge compared to our last place, and everyone got their own bed. Glorious.
We’re not Disney fanatics, but we took advantage of the evening pass — a great option since the hotel was so close and four hours of theme park time is plenty. First stop: curry and popcorn. I only did a few rides because my wait time limit is 10 minutes max. Mostly, I just enjoyed the vibe. Highlights included It’s a Small World (classic) and the evening parade. Locals take parades seriously — they lay out towels hours in advance to save spots. Eventually, we all went our separate ways and planned to meet back at the hotel. I left around 8:30, grabbed a snack at the grocery store, and caught the hotel shuttle. Kayla, of course, stayed until closing.
Day 4
I squeezed in a waterfront run—an out-and-back that reminded me of Milwaukee. I was missing my Milwaukee crew and feeling a little lonely on my morning runs. I’ve yet to regret a run on vacation because it is one of the most efficient ways to see a new place and usually gets you off the beaten path a little bit, giving you a different perspective of the city you’re visiting. However, it can be a little intimidating to be a solo young female out running in a place you are unfamiliar with. Times like these I wish my sister was a little more into running (or just willing to bike next to me on the occasion that it’s possible)!
We headed back to Tokyo Station and explored areas I’d run through earlier. Everyone else strolled through the Imperial Palace gardens, while I went off in search of a pastry and good coffee. Since I had been going on my morning runs in this area, I felt like a local. We agreed to meet at the Palace Hotel, but… fun twist: there are two of them. Kayla led Mom and Dad to the “less fancy” one, while I went to the luxury version. I sent them photos. Kayla had FOMO.
Kayla went off to meet an old coworker who’s now stationed in Japan, while I took our parents on a sightseeing tour. I thought it might feel like babysitting—but honestly, it was refreshing. The dynamic felt calmer without Kayla’s spontaneous detours. Love you, Kayla, but with her, there’s always a sense of pressure to maximize every moment. I think she gets caught up in wanting to make sure we’re doing the best possible thing at all times. But that mindset can lead to second-guessing, indecision, and stress.
What I’ve started to realize is this: the worst decision is often not making one at all. It’s better to just choose a plan, stick to it, and be fully present in the experience—whatever it is. You can always reflect and adjust for the future, but there’s no point in spiraling into could’ve, should’ve, would’ve over what’s already behind you.
We started at Ueno Park, which was a hidden gem—lots of flowers, temples, a zoo, and a ceramics pop-up market. Mom and I found beautiful handmade bowls and small stones for displaying flowers. We kept thinking, “Kayla would love this,” which was true and after sharing the photos she entered the could’ve, should’ve, would’ve spiral thinking about what alternate scenario would’ve led to her also being able to go to the ceramics pop-up.
Next up: Senso-ji Temple. But the real attraction in my eyes were the people watching and the nearby streets filled with charming cafes and snack shops. I liked seeing people dressed up in traditional outfits and having photoshoots. After photobombing we got matcha and black sesame ice cream. They had 7 different matcha flavored gelatos, ranked weak to strong. I went for the strongest matcha flavor, of course. We also tried sweet buns filled with red bean, lemon, and sesame. Mom grabbed a roasted sweet potato from a grocery store that totally exceeded expectations. Our afternoon turned into a food tour.
We strolled along the river and made our way to the Tokyo Skytree, eventually heading all the way to the top. Normally, I skip the whole “tallest-building-with-a-view” tourist trap—especially when it feels like a checklist item—but this one genuinely surprised me. The view gave me a whole new appreciation for the sheer scale of Tokyo. It’s not a skyline filled with towering skyscrapers like New York, but it stretches endlessly in every direction—dense, layered, and sprawling in a way that’s hard to comprehend. Over the past few years, I’ve grown into my identity as a city girl—someone who loves being able to walk everywhere and feel connected to a neighborhood. But standing above Tokyo made me rethink that label. I think I need to add some parameters: I’m a city girl, but would like to live only in cities bigger than Milwaukee and less overwhelming than Tokyo.
We had planned to stick around for the sunset, but the observation deck was hot, crowded, and getting increasingly chaotic. I could feel myself nearing the tipping point where excitement turns into exhaustion, and I’ve learned to pay attention to that. Sometimes the key to a good memory is knowing when to leave—before you’re too hungry, too sweaty, or too overstimulated to enjoy it.
With a positive lasting impression of Tokyo Skytree we ditched the sunset and went in search of food. We ended up at a mall food court. It was low-key, everyone could get what they wanted, and there was no pressure to make a perfect choice. I got sushi and cold soba noodles, which was refreshing after a long day. Not a fan of the soft-boiled egg, but I actually liked the natto—fermented soybeans that reminded me of tempeh. I love trying new things, and today was full of them. It felt like the right balance of structured adventure and letting things unfold.
Day 5
I went for one last run, reversing my previous route and heading toward a nearby town instead of the industrial zone. It was a neighborhood where locals actually live—less touristy, more real. It was charming. People were out walking their dogs, chatting, just living. I felt like I got to peek into ordinary Saturday morning life.
Then we packed up and headed to the port. Some of us (cough—Kayla) had significantly more luggage than others, so it made sense to go straight to the cruise terminal.
