After our terrific four day stint in Kyoto, we had six days remaining in Japan, which would be split across three destinations (two days in each place). Next up was Osaka, which was also fortunately the quickest and easiest route of our trip. I was initially on the fence about Osaka, since I had researched a lot of itineraries that skipped Osaka. However, I then found a NYT “36 Hours in Osaka” article that made the argument that although many visitors to Japan skip over Osaka, it was worth a visit. I was sold, and carved out a couple days in the second largest metropolitan area of Japan.

As we made our way through Japan, we heard good things about the city from other travelers. While Osaka doesn’t feature as many temples, shrines and other architectural sights compared to many of the other popular tourist destinations in Japan, it does offer a thriving food and nightlife scene. Maybe we would finally get out of our comfortable “Grandma” routine of dinner and bed in Osaka!

One other thing that we had to look forward to in Osaka: good weather. The forecast was predicting some of the warmest, sunniest days of our entire trip while we were in the city. I sometimes feel like I have a slight case of Seasonal Affectiveness Disorder because sunny, blue skies always lift my mood (not sure why I ever thought I’d be happy living in Seattle, but I digress). Lauren and I were both ready for some more temperate weather.

Getting to Osaka and the St. Regis

As I mentioned, the train to Osaka was the easiest, quickest transfer of our entire trip. Another reason why it made sense to visit Osaka. We could have taken the local train to the JR train and used the IC cards and JR passes that we had already purchased, but the privately run Keihan Main Line enabled us to ride on one train without transferring. We’d have to buy a ticket… but it only cost 410 yen (about $4 USD). No brainer.

We had assumed that it would be easy to get a taxi from Osaka Station (otherwise it would have been nearly an 18 minute walk with our luggage). Well, maybe we took the wrong exit because we walked out of a large office building attached to the train station and found ourselves on a busy city street with no taxi queue in sight. Hmm. We hadn’t yet hailed our own cab in Japan, but we were New Yorkers. We should be pros at this, right? We crossed the street to get slightly closer to the direction we were headed and stuck out our hands as the oncoming traffic whizzed by us. Eventually, an empty taxi started to slow as he neared us and turned on his hazard lights. Woohoo! Then… he passed us and pulled away, leaving us staring at his taillights in confusion. WTF. Maybe we were out of practice at hailing cabs in the age of Uber and Lyft.

A few minutes later we redeemed ourselves and settled in to our well-earned taxi. Of course, we then had to go through the usual process of trying to communicate where we wanted to go, pointing to Google Maps, gesturing animately with our hands and helplessly explaining the directions in English. Our driver finally seemed to understand and figure out the route on his own navigation system, and we were off. As usual, I followed his path closely with Google Maps to ensure we were in fact going in the right direction.

We arrived at the St. Regis with minimal issues, surrendered our bags to the bellhop and headed up to the lobby on the 12th floor. We were able to check in, but were then informed that our room wasn’t yet ready for us (we arrived about an hour before our check-in time of 3pm). For the record, this was the only time this happened in Japan, even though we had arrived early several times previously. The St. Regis is not always perfect. However, I was ready to forgive them. My Titanium Elite benefits offered us standard perks like late check-out and a room upgrade, and we were also given a 3,000 yen/night minibar credit (almost $60 total over our two night stay). One of my vices is raiding the minibar, and I don’t think I’ve ever been given a minibar credit upon checking in (in fact, many times F&B credits exclude the minibar). It’s the little things…

It wasn’t a big deal that we couldn’t get into our room because we had already been discussing checking out Osaka Castle upon arrival. Osaka Castle is one of the major historical attractions in the city, and it was also supposed to be a prime spot for cherry blossoms. The walk was about 30 minutes from our hotel, but we were ready to stretch our legs a bit, and the weather really was pretty perfect.

The walk wasn’t the most scenic, but we did come across the most hysterical sight of an older man pushing a buggy full of little dogs. I’ve honestly never seen anything like it.

The man was happy to stop and pose for some photos
This pup was even rocking sunglasses

We arrived at the large grounds of Osaka Castle and discussed our plan of attack. We’d walk the straight shot to the castle, then circle back around to the line of cherry blossom tress in full bloom.

The castle was a pretty impressive sight. Dating back to the 16th century, the grounds include 13 structures and a large moat. Many of the structures have been burnt down and/or damaged in armed conflicts multiple times over the years, but everything has been reconstructed and restored for visitors in modern times. (Are you noticing a trend here?) The downside was that it was very crowded. We could’ve gone inside and up to the top of the castle, but there was a long line, and we weren’t patient enough to wait. Plus, there was another structure near the castle that appeared to feature a rooftop bar. We could see the people milling around up there, overlooking the imposing view of the castle. Yes, that was where we wanted to be.

Central tower of Osaka Castle
Moat surrounding the castle

Except then we got to the third floor restaurant and were informed that it was closed. What? But there were people up there. Never one to take no for an answer, Lauren then spotted a sign for the rooftop terrace saying that it closed at 4pm (it was now almost 3pm). Hmm, the woman must have misunderstood where we wanted to go. We got into the elevator with two women and a stroller and pushed the “R” button. As the elevator doors opened, we were greeted with a sign that said “CLOSED.” Really? We pushed past the sign and could see people in seats. Then I saw a red carpet leading down an aisle and realized that the people were seated in rows on either side, facing a podium where some men in suits were lined up.

Ohhhhh, the rooftop bar was closed for a wedding. It all seemed to make more sense. Lauren attempted to sneak to the edge of the roof to take some quick pics, but was quickly shooed away. We filed back into the elevator as a woman in a fancy white dress appeared at the foot of the aisle. Oops! We definitely didn’t belong here. I felt a little bit better that we weren’t the only people attempting to crash the wedding, as we all dejectedly rode the elevator to the ground floor. Well, at least the bride and groom lucked out with a perfect day for their wedding.

Back outside with everyone else, Lauren and I decided we had to indulge in some of the rosé we had seen being served throughout Japan at all of the popular sakura viewing spots. We took our plastic flutes and settled into seats on a bench, appreciating the sun-drenched view of the castle and the cherry trees. It wasn’t exactly a rooftop, but it wasn’t bad at all.

Chandon was definitely capitalizing on the demand for pink champagne during sakura season

Next we wandered through the grounds, admiring all the groups of people picnicking amongst the beautiful sakura. It was a Saturday afternoon, so the crowds were out, and people had clearly been enjoying themselves.

One thing that I had begun to notice in Japan: as orderly and proper as the culture seemed to be, there didn’t seem to be any taboo about sleeping in public. It was not uncommon to see people sleeping on public transportation, and we saw numerous people sleeping in the parks after a long day of celebrating in the sun.

I was impressed that these men were able to nap with all the commotion happening around them

We meandered out of the park and headed back to the St. Regis. Lauren was starting to feel better, but she was just regaining her appetite and wanted to take it easy for dinner. However, I had made reservations at Shiotsu, a Michelin-starred sushi restaurant. Given the tiny nature of the place (eight seats at the bar and a private room), I worried about being able to cancel, or even changing the reservation to one person instead of two. The restaurant only offered an omakase menu (omakase means “I’ll leave it up to you” in Japanese). This meant that Lauren couldn’t make her own choices about the menu, and some of the menu items could be on the eclectic side. However, it would all be very fresh, as the restaurant had likely already sourced all the fish for the meal at the market earlier that day.

Rather than trying to attempting to explain the situation to the restaurant ourselves, we asked the concierge If she would be able to help. She agreed that it was unlikely we’d be able to cancel without paying the full price of the meal, but we asked her to see if there was anything that could be done to offer Lauren a pared-down version of the menu. After calling them and speaking for a while, we came up with a solution. The restaurant would offer Lauren a lower set price for the meal, and they’d also do their best to accommodate any preferences she had (but couldn’t promise anything). I was pleased that the restaurant was able to be somewhat flexible, and also happy that Lauren was going to be able to join me for dinner.

Finally, we were ready to get into our room. We had been given a beautiful corner room on the 24th floor with tall ceilings and sweeping views of the city. The highlight was the bathroom, particular the centerpiece bathtub. Framed by a floor-to-ceiling window, the bathtub was placed to have a perfect view of the sunset. While I wasn’t going to be taking a bath during this stay, it was still nice to get ready at the double vanity with the view of the city looking back at me in the mirrors.

Bath with a view

Dinner at Shiotsu

After a couple hours relaxing in the room and getting ready, we headed downstairs to get a taxi. By this point, we knew what to expect from a taxi ride in Japan: a lot of commotion when explaining the destination to the driver as he consulted his navigation system to ensure that he knew precisely where to take us (even with the St. Regis able to help communicate in Japanese). Then the taxi driver would take a very careful, sometimes inefficient approach to dropping us off right in front of our destination, which was typically on a difficult-to-find alleyway or one way street. Often, the driver would stop at the intersection closest to our destination, jump out of the car without explanation, literally run down the street to ensure he knew exactly where to bring us, and then come back (this sometimes including us watching the driver run both ways down the street as he searched for the hidden restaurant or bar entrance). It was hilarious, and we couldn’t help but appreciate the effort that the taxi drivers put into doing their job as perfectly as possible. While it sometimes would have been more efficient to just drop us off at the corner and let us walk the rest of the way, the drivers did not find this to be acceptable course of action.

The St. Regis had been very helpful by printing out a map of the area around the restaurant, along with a picture of the entrance so that we and the driver all knew exactly where we needed to go. The restaurant was located up a stairwell on the second floor of a small building on a one way street, so the effort was much appreciated.

We walked into the tiny restaurant, which was essentially a brightly lit room with an L-shaped sushi bar containing eight seats that surrounded the chef. This allowed us to watch everything that he did, and our side seats gave us a great view of his station so we could assess his knife skills (very impressive). Just like the other traditional, high end restaurants we had visited, the room felt hushed initially, and somewhat stiff and formal. I found myself feeling a little uncomfortable at first, as we were a few minutes late after our taxi driver’s best efforts to get us to the front door, and we had been marked as the high maintenance party that wanted a special menu. We were also the only foreigners at the restaurant, which I observed as a good sign that the locals approved of this place.

View of the chef from our bar seats

The initially formal atmosphere gradually relaxed as we interacted more with both the sushi chef and the hostess of the restaurant (we later learned that they were the husband-wife owners of the place). We ordered some sake and were presented with the option to choose our own glasses from a collection of beautifully colored crystal.

We ended up ordering three small carafes of sake (which in total equated to less than a bottle of wine, in case you were wondering). Each time, the chef made his own bottle selection to pair with our upcoming dishes and we got to choose a new glass.
The restaurant was very accommodating with Lauren; she had told them she didn’t like squid but did like tuna, so we received different dishes for our first course
They also gave Lauren a smaller version of miso soup for the soup course. I was obviously the fatty of this meal.

By the end of the long, multi-course meal, we had started to make some small talk with the owners, despite the language barrier (the wife spoke better English than the husband, so that helped). We provided each other with language lessons and joked around a bit. They asked us what we did for work in the States. Rather than attempt to provide the long explanation of why I was unemployed and what I did previously, I decided to keep it simple. “I work in technology. Have you heard of Snapchat?” They hadn’t. Well, time to whip out the app and show them. Hilarity ensued.

We showed them how filters worked
The wife burst out laughing at this filter that added 20-30 years to her husband’s appearance
Not sure what happened with this one…

We eventually paid our bill and asked if the wife could help to call us a cab. Of course she could. Then she insisted on walking us outside and helping us get into the cab, where she waved enthusiastically at us with both hands while we drove away. Aww, so sweet. Lauren and I both agreed that the Shiotsu meal was one of our favorites of the trip. The food was excellent, and the warm hospitality was a wonderful surprise.

As it was Saturday night and we had heard good things about the lively Osaka nightlife, we were considering a post-dinner excursion, but after a three hour meal, we were ready to call it a night. Wah-wah. Sorry if I seem boring on this trip.

Hanami Day

After a good night’s sleep, a workout in the hotel gym (okay, but no Park Hyatt Tokyo) and breakfast, we were ready to make the most of our only full day in Osaka. And that meant… day drinking, which I thought was fully justified for the following reasons: 1) Osaka doesn’t really have that many sights to see, 2) It was another beautiful, pleasantly warm day, and 3) The cherry blossoms were in full bloom. Because of #2 and #3, all of the locals were out celebrating. So far we had only observed the hanami parties happening all around Japan, but we hadn’t really participated ourselves. This was our day to immerse ourselves in the cultural experience!

While we didn’t have a sturdy blue tarp that the Japanese seemed to prefer for their hanami blankets, I had brought my own picnic blanket for just this occasion. I was thrilled that I hadn’t wasted precious luggage space for no reason. We found a grocery store conveniently located en route to the Osaka Castle Park and we were on our way.

Similar to our experience grocery shopping in Kyoto, buying groceries in Osaka was an experience in and of itself. We roamed the aisles, marveling at all the unique products that stocked their shelves. We ended up with an assortment of salads, snacks, fruit, and of course, wine. We opted to use the self checkout line to pay and somehow managed to get through with our minimal (okay, nonexistent) Japanese language skills. My favorite part of the whole process was the sound that the self checkout station made every time I scanned an item. Instead of a boring beep, it actually neighed like a horse. It was like shopping with Mr. Ed! We couldn’t help but giggle the entire time.

Arriving at the park, we made our way down the path of cherry trees and attempted to find the perfect spot that provided a mix of sun and shade. The park was packed, but it wasn’t too hard to find a small patch where we could squeeze in.

Our hanami spread – we weren’t messing around

We got settled and admired the scene around us. People of all ages were gathered in groups, smiling, laughing, joking, eating and drinking all varieties of beverages and cuisine. The atmosphere was convivial and we admired how inclusive the party was. It seemed like everyone from the greater Osaka area had gathered here together. 

Such a fun and festive scene
How freaking cute are these two?!

At first we kept to ourselves, but after an hour or two, we eventually started to make friends with the family sitting next to us (adult son, his wife and his parents). Between their broken English and Google Translate, we were able to tell them a little bit about our travels so far in Japan, and our future plans. They asked us what we did in the States, and were impressed that Lauren was a nurse. I told them I worked in technology, and once again the Snapchat app came out to delight everyone.

No language barriers when Snapchat is involved
I look drunk in this picture, but I really just chose the wrong time to blink

We eventually had to get going to prepare for our evening, so we gave them the Suntory Highball that we weren’t going to drink, and they returned the favor with packets of salty snacks. They also gave me a plastic bag for my picnic blanket so that I wouldn’t get grass and fallen cherry blossoms in my leather tote. I really did love Japanese hospitality. It took them a while to warm up sometimes, but once they did, they would do everything in their power to make sure we were comfortable.

Sunday Night Bar Crawl

Back at the St. Regis, we stopped at the bar for a drink because, well, we had to see it. The St. Regis bars worldwide are known for their beautiful murals, and the Osaka property was no exception.

Bar at St. Regis Osaka

For our last night, we had found another Airbnb experience that was essentially a bar crawl that would also provide the opportunity to eat some food. Similar to the Airbnb experience that we did in Tokyo, we’d go to local izakayas with standing bars where the menus were all in Japanese and the staff didn’t speak any English. Since we had been struggling to get ourselves to go out after dinner throughout our entire trip, it was also a good opportunity for us to experience some of the nightlife, even though it was a Sunday.

We met our guide, Aki (a woman) and our three bar crawl mates: a guy from South Korea, a Korean woman that now lived in the States and an American woman that also lived in New York. All three of them were traveling solo, which always made me happy to see.

Aki was an enthusiastic and friendly guide that spoke excellent English (she had attended university in the States). At the first bar, she explained the menu to us, and we each chose the drink and the dish that we wanted to order. She then helped us to pronounce the necessary words so we could order for ourselves. Next, she instructed us on how to get the attention of the servers so we could place our order. Oh, I already knew how to do that. 

“Sumimasen!” I called out loudly, and a woman scurried over toward us. “Very good!” Aki told me. I beamed for a moment, but knew that my proud moment wouldn’t last. I had chosen to drink a highball, which was an easy order: it’s still called a highball in Japan. Perfect. I now had a go-to drink if I ever found myself alone in a Japanese bar with no English speakers. I honestly don’t remember what I had to eat (something veggie), but I do recall that I totally bungled the order and was very happy to have Aki there as back-up.  

We enjoyed our food and drinks, and then Aki brought us to our second stop. Once again, we went through the process where Aki explained the menu, we made our selections and we learned our orders. I chose a shochu cocktail this time (again, don’t remember what it was called), as well as three different veggie skewers (onion, sweet potato and tofu). I wasn’t very confident in my ability to order four different items when I had done so poorly ordering a single dish at the last place. If I had been able to see the words spelled out with their phonetic pronunciations, I would have been better off, but I was still going to make an attempt. Aki stood to the side at the counter, ready to prompt me if needed.

That didn’t go very well… at least I could laugh at myself

We chatted a bit more with the group once our orders were in, and were all shocked to learn that the Korean-American woman was 45 years old. What?! She looked younger than I did. Then Aki said she was the same age. No! I thought she was closer to my age. Damn, those Asian genes sure are impressive.

Several of our drinking buddies (Aki is on the right)

The Korean-American woman was actually married (no children), but her husband didn’t like to travel, so she left him at home and went places on her own. Good for her. Aki then opened up a little more about her life as a forty-something single woman living in Japan. “I’m seen as a lost cause,” she said. It sounded like she had given up on the idea of ever falling in love or getting married because of her age. Things like that just didn’t happen once you reached a certain age, she told us. She did seem a little sad about it, which I found depressing. I don’t want to generalize about the entire culture in Japan based on one woman’s point of view, but Aki was conveying to us that the expectation was that women were supposed to get married, and if they didn’t achieve this goal by a certain age, they were a failure. I know that is still the case in a lot of countries, but I was surprised to hear this perspective from someone who otherwise seemed very confident and self-sufficient.

We had one last round of drinks at a bar down the street and discussed moving to the main scene of Osaka’s nightlife. However, I was tired after a long day and we had another big travel day ahead of us. We bid farewell to our new friends and took a taxi back to our hotel (thankfully, we had a card with the address printed in Japanese, so it wasn’t too difficult to convey where we wanted to go).

And that was it for our weekend in Osaka. I’m very glad that we fit the city into our itinerary, but we still had several more places to see: Hiroshima, Miyajima and Hakone.