Japan Day 1: We Finally Made It to Osaka!

After months of planning, our Japan adventure had finally begun.

When I booked our flights, there weren’t any direct options from Montreal to Osaka. I chose an itinerary with a stop in Vancouver because it split the trip into two more manageable flights instead of one extra-long journey.

For the return trip, however, I did the opposite. We flew directly from Tokyo to Montreal. After three weeks of travelling, boarding one plane and waking up back in Canada sounded much more appealing than adding another airport connection.

Another decision that made our trip much easier was flying into Osaka and home from Tokyo.

Many visitors book a round-trip ticket to Tokyo, but since our itinerary naturally moved east – from Osaka to Kyoto and finally Tokyo – it would have meant spending extra time and money travelling back across Japan just to catch our flight home.

Instead, we could simply enjoy the journey one city at a time.

Packing Light… on Purpose

I also didn’t want the three of us dragging large suitcases through train stations every few days.

Our solution was surprisingly simple.

Each of us travelled with a carry-on suitcase (which we checked for the flight to Japan), a backpack, and a foldable travel bag packed inside the suitcase.

Those foldable bags weren’t an afterthought – they were part of the plan from the beginning.

We expected to do a little shopping in Osaka and Kyoto, but we knew Tokyo would be our biggest shopping destination. The foldable bags would become extra checked luggage for our flight home, giving us plenty of room for souvenirs without carrying oversized suitcases throughout the trip.

There was one more reason behind this strategy.

Before leaving Canada, I had already decided that we would buy one suitcase in Japan – not because luggage is necessarily cheaper there, but because I wanted kid 2 to have a medium-sized suitcase for future trips.

My dream was to find a cute Hello Kitty suitcase.

As you’ll see later in this series… things didn’t quite go according to plan, but I couldn’t have been happier with how it turned out.

Our First Steps in Japan

After landing at Kansai International Airport (KIX), our first challenge was simply finding the train station.

The airport is well organized, but after a long international flight, even simple directions can seem confusing. We checked the signs a couple of times before reaching the train terminal, and it turned out to be much easier than we expected.

Before leaving Canada, I’d also made sure we’d all have internet access as soon as we landed. I used a travel pass from my Canadian provider and shared my connection as a hotspot when needed. Kid 1 used an eSIM, while kid 2’s phone required a physical SIM card. We each had the solution that worked best for our phones.

Our first official task in Japan was buying our transportation cards.

Buying Our ICOCA Cards

We bought three ICOCA cards directly from the vending machines.

I had wondered beforehand whether the machines would be difficult to use after such a long travel day, but the whole process was surprisingly easy.

One tip that’s worth knowing: when we bought our ICOCA cards, the vending machines accepted cash only, so make sure you have some Japanese yen with you.

Within a few minutes, we were ready for our very first train ride in Japan.

If you’re visiting the Kansai region, I highly recommend getting an ICOCA card as soon as you arrive. It works on most trains, subways, and buses, making transportation incredibly convenient.

At the end of our trip, we decided to keep our ICOCA cards instead of returning them. Since we had bought them in the Kansai region, returning them in Tokyo wasn’t practical before our flight home. Rather than making a special trip back to a refund location, we kept them as little souvenirs from our adventure – and hopefully we’ll use them again on our next visit to Japan.

The Hello Kitty HARUKA Express

Of course, we couldn’t resist taking the Hello Kitty HARUKA Express into Osaka.

Was it cute? Absolutely.

Was it worth making a detour just to ride it? Honestly… probably not.

If it’s already the train you need, it’s a fun little bonus. But I wouldn’t change my itinerary just for the Hello Kitty decorations. The train itself is very similar to the regular HARUKA service.

The Best Decision of the Day

Once we arrived at Tennoji Station, we made what was probably the best decision of the day.

We took a taxi to our Airbnb.

After almost a full day of travelling, the last thing any of us wanted was to navigate unfamiliar streets while pulling luggage in the summer heat.

The taxi wasn’t expensive, it was comfortable, and it allowed us to start our vacation feeling relaxed instead of exhausted.

Sometimes convenience is worth every yen.

After nearly a year of planning, we had finally arrived.

Everything we’d looked at on maps, watched in YouTube videos, and imagined for months was suddenly real.

Our First Japanese 7-Eleven

After settling into the Airbnb and taking a short break, kid 2 and I headed to the nearest 7-Eleven while kid 1 stayed behind to rest.

We weren’t looking for anything in particular.

We simply wanted to explore.

I’d watched countless YouTube videos while planning this trip, and almost every one of them made the same claim: “The food at Japanese convenience stores is amazing!”

So naturally, we had pretty high expectations.

Walking through the aisles was definitely fun. There were fresh meals, rice balls, sandwiches, desserts, drinks I’d never seen before, and enough snacks to make choosing difficult.

Over the course of our trip, we tried quite a variety of food from 7-Eleven, Lawson, and FamilyMart.

Our verdict?

It was good.

But honestly… not that good.

Maybe YouTube had set the bar a little too high.

We actually found that supermarkets offered even more variety. The prepared food there was good too, but neither convenience stores nor supermarkets turned out to be the incredible culinary experience we had been expecting.

One exception, though, was the smoothies at 7-Eleven.

Those quickly became one of our favorite convenience store treats, and we happily bought them more than once during the trip.

Things We Learned Today

• Flying into Osaka and home from Tokyo saved us from backtracking across Japan.
• Packing light, with foldable bags for the trip home, made travelling between cities much easier.
• Buying an ICOCA card at KIX was quick and easy, but the vending machine required cash. And if you buy one in Kansai, don’t assume you’ll be able to return it in Tokyo.

Next up

Our first full day in Osaka brought a little bit of everything: shopping, fresh fruit mochi, plenty of rain, and our first major attraction.