Okay everyone… welcome back to the blog where I’m unpacking mine and Justin and the kids’ trip to Japan!
If you missed the first post, I shared the full story of how this trip came together (there were a lot of pivots lol)… but Japan was always kind of the dream for our honeymoon. Somehow we ended up back there, and I’m so glad we did.
If you want the full backstory, I’ll link that blog here.
For this series, I’m going to break everything down city by city… starting with Tokyo, then sharing all the other places we visited across Japan. So keep checking back if you’re planning a trip or just following along.
One thing to keep in mind as you read these… we booked this entire trip about 10 days before leaving. 😅
So if I were to do anything differently, it would be to book at least 3–6 months in advance. We definitely had some limitations when it came to accommodations because of that. But honestly… everything still worked out so well.
Tokyo was our first stop… and it truly was everything I imagined it to be. Electric, vibrant, full of life… just such an incredible place to kick off the trip.
Getting There (With Kids…)
We flew Kelowna → Seattle → Tokyo, and I have to say… it was actually way easier than I expected.
We travel to Hawaii quite a bit and it felt really comparable, and definitely easier than heading to Europe.
We landed around 3:30pm and felt really good. Of course the time difference hits (it’s about 17 hours), but for us it wasn’t too bad overall. The kids felt it a bit more than we did, but nothing unmanageable.
We did find ourselves waking up early the next morning, which is something to keep in mind… Tokyo doesn’t really get going until later in the morning. So just plan ahead a little and have something in your room or a bit of a plan for those early hours.
Where We Stayed in Tokyo
We stayed at the Westin Tokyo, and it ended up being such a great home base. The lounge was honestly one of the highlights. We started most mornings there and it was such a nice way to ease into the day. The breakfast spread was incredible… dumplings, omelettes, tofu, yogurt, smoothies… everything you could imagine. And the view over the city while having your morning coffee was so good.
It was also just really nice to come back to after a full day out.
Also just a note… nothing on this trip was sponsored. We chose the Westin because of points, availability, and familiarity… and it ended up being exactly what we needed.
Honest Thoughts About Tokyo
Tokyo is busy, exciting, and completely unique. There is so much going on everywhere you look, and it really does live up to everything you imagine. Justin and Leo absolutely loved it… they could have stayed longer and kept exploring.
And looking back now… I would actually love to go back too. I think at the time, I was just taking everything in for the first time… the pace, the newness, the weather wasn’t amazing… but now looking back at photos, I wish we had a couple more days just to wander and explore more slowly.
Because that’s really what Tokyo is… neighbourhood by neighbourhood, there is so much to see.
Tokyo Highlights (What We Actually Did)
We did all the things… Shibuya Crossing (which… I’m sorry… slight letdown 😂 it’s a crossing), Meiji Shrine, wandering, shopping… just taking it all in. One thing I’m actually really glad we did was organize our days by neighbourhood. Tokyo is huge, so even when you’re staying in one area, there is still so much to see and do. Grouping things together helped a lot and made the days feel more manageable.
That being said… I still felt like I could have spent more time in each area. There is just so much to see, and I often found myself wanting to stay longer and wander more.
The kids had their own highlights… The Pokémon Centre was a huge hit (and I definitely regret not buying more Labubus… they were so cheap 😂). They also loved the cat café… which wasn’t really my thing, but they were very into it.
Getting Around Tokyo
Getting around Tokyo definitely takes a little bit of getting used to… which is expected in a city that big. We travel a lot and still found ourselves double checking directions and figuring things out as we went. Once you get the hang of it, it’s great… it just takes a bit at the beginning. We did use Uber quite a bit as well, especially with the kids, and it made things really easy when we needed it.
The Food!
The food was incredible. There are so many amazing spots everywhere, and it’s very easy to overthink where to go… especially if you’re trying to find those “viral” restaurants. If that’s something you want to do, I would definitely recommend having a bit of a strategy. Either make a reservation (which can be tricky if you’re wandering all day and don’t know exactly when you’ll be ready for dinner)… or get there early. And by early… I mean like 1–2 hours early. Yes, I said it 😂 Put your name down, grab a ticket… Japan is very much a ticket system… and then go wander and come back.
We found a lot of the places we wanted to go had 2–3 hour waits, or they would just cut off the line completely by 6 or 7 because they were already full for the night. So that’s definitely something I would do differently next time… just have a bit more of a dinner game plan.
Justin’s Birthday in Tokyo
This day was so special.
We started the morning with a full birthday setup… very Jillian Harris style 😂 I had Leo helping me blow up balloons quietly in the bathroom at like 5am while Annie and Justin were still sleeping… which honestly made it even more fun.
Then we went to Ivy Place for breakfast… which was amazing. I still think about that meal.
The boys found a little car show, and then we went to this incredible bookstore that (I’m pretty sure?) was owned by Starbucks… it was SO cool. We spent so much time in there just wandering and looking around.
Then of course… Pokémon Centre.
That night we went to a baseball game at the Tokyo Dome and it was honestly one of the highlights of the trip. The energy, the chants, the atmosphere… even if you’re not a baseball fan, it’s such a cool experience.
Dinner that night was a bit of a miss (I didn’t make reservations and it was a Sunday… lesson learned 😂), but we made it work.
We had checked out of the Westin that morning but left our bags there, did all of the birthday things, and then went back later in the evening to grab them before heading to Disney. Honestly, I would do this exact setup again. It made the day feel really easy and not rushed at all.
And that kind of leads into the next part… If you’re doing Disney, I would absolutely recommend getting there the night before so you wake up already in Disney and can just start your day. It makes a big difference.
Our Tokyo Itinerary
I always like seeing this in blogs, so here’s how our days roughly looked…
Day 1 – Arrival + Ease Into It
We landed mid-afternoon, checked into the Westin, kept things super low key. Walked around, got our bearings, had an early night.
Day 2 – First Full Day
We had breakfast in the lounge (amazing!!!!) saw the Tokyo Tower and took the train to Shibuya. Had sushi for lunch and then wandered over to Takeshite Street. This area is where the cat cafes were. It was very overwhelming, but I’m glad we did it, and actually wish we had more time in this area. Next up, we went to Meiji Shrine. The walk was so GORGEOUS. We finished off the day with ramen for dinner (and yes… Annie fell asleep in her ramen LOL). The kids were DONE by this point, so we decided to call it a day and head home to bed.
Day 3 – Exploring
Started the day with an early morning lounge breakfast and then explored Asakusa in Taito City. We walked through the iconic Kaminarimon Gate (you might recognize the big red lantern) and visited Sensō-ji Temple (we absolutely loved this area). Then we headed back to Ginza to visit Hakuhinkan Toy Park, which was a little overwhelming for adults but pure joy for the kids. Unfortunately, this evening, our dinner was a bust, so we had to order McDonald’s LOL.
Day 4 – Justin’s Birthday
We started off Justin’s birthday by going for breakfast at Ivy place and it was amazing. The boys found a little car show which was super fun. Then, we found a little book store that looked like it was owned by Starbucks and it was SO cool. We spent probably an hour there shopping and looking, then we were off to Pokemon Centre. After that, we went back to Shibuya, it was sunny this day and I actually wish we more time in that area, but we had plans to go to a baseball game that evening! Unfortunately, dinner was also a bust this day (Sunday + no reservations), but we found a little hole in the wall restaurant and had a traditional Japanese dinner. After dinner, everyone was so exhausted, but it was time to Uber to Disney. BIG ASS DAY LOL.
Final Thoughts on Tokyo
I’m so glad we started our trip in Tokyo. It’s such an incredible introduction to Japan… the culture, the energy, the food… it really sets the tone for everything. And looking back now… I would absolutely go back and spend more time just wandering, exploring, and soaking it all in.
Next up on the blog… Disney Japan… and I have a LOT to say about that one 🎢✨
If you have any Tokyo questions, leave them below or send me a message. I’m so happy to share anything we learned along the way!!
xo
Jilly
