Trip Report August 2023: 9 days in Japan (Tokyo, Kyoto, Osaka)

Posting a very belated trip report from me and my partner’s travels in August! We are in our 20’s and did 5 days in Tokyo, 2 days in Kyoto, and 2 in Osaka. We had an amazing time and did a medium amount of planning before our trip. First off some tips based on our trip and then the full travel report:

1. Don’t blindly follow “top food” lists for Japan. My boyfriend is a huge foodie so his main focus of the trip was the food while I focused on activities. He made a few reservations beforehand for things like a traditional kaiseki, and he also had a list of places he found on travel blogs. We ended up doing a lot more random popping into places than we had anticipated, but I’m so glad we did. Almost every time we would go to one of the places we had found from a list, the food was not as good as the random places we would just walk into. The food in Japan is super high quality and delicious basically anywhere you go, so you can’t really go wrong tbh. I would just recommend having a list of the main foods you want to try (like my boyfriend made a list for us that included ramen, japanese curry, omakase, kaiseki experience, izakaya, soba, etc.).
2. If you can, avoid going during the summer months of typhoon season. We had to go in August because we planned our trip around my friend’s wedding in Korea, but if we went again I would definitely prefer the fall or spring. It was so humid the entire time that I had to wear my hair gelled into a ponytail every day or else it would completely frizz out within 20 minutes of being outside. It also rained quite a bit so we’d have to change some of our plans or take breaks based on whether it was downpouring. The only plus of the clouds and the rain was that it definitely made the heat a bit more bearable. We got like one day of full sun and realized we preferred the clouds because the 90+ degrees of heat with direct sun made it harder to enjoy walking around outside.
3. Don’t be afraid to talk to the locals. I personally always feel annoying as a tourist but my boyfriend would just strike up conversations with people and they were always so nice and welcoming. The people in Japan were one of the reasons why our trip was so great and it was awesome getting to know more about their culture by speaking with them. We also got so many great recommendations from everyone we spoke with that really influenced our trip and made it even better.
4. Don’t stress if you don’t make it to the top tourist destinations or don’t have everything completely planned out. There were some things that I really wanted to do like Nara, TeamLabs, and Ghibli Studios, but we ultimately didn’t get to do them. Going into the trip I was very stressed that I had not planned enough and every day I was nervous that we were going to waste a day if we didn’t do x amount of activities. Even just walking around you see so much and there is always something to go see, and so many activities that may not be as popular but are still an awesome experience.
5. Also don’t stress if your itinerary plans have to change. There were a decent amount of times when something we planned to do wasn’t open yet, or closed early, or it was pouring rain so we would have to pivot. It would make me upset if we weren’t able to do something at first, but then throughout the trip I realized we were having so much fun even when we had to change our plans and do something outside of our itinerary. It will likely happen as no trip ever goes completely according to plan, so just embrace the spontaneity and go with the flow.
6. Booking some tours really helped get to know the history and culture of the areas better, and also have fun with a new group of people. We had 2 food and market tours in Tokyo, and one in Osaka. They were definitely worth the cost and allowed us to take away the stress of figuring things out on our own and just having a tour guide explain everything which was a nice change. It also allowed us to find small local places that we probably typically would not have gone to.

August 12th:

We arrived to the Tokyo airport at around 2pm, got to our hotel in Shinjuku around 5pm then explored nearby area. We got an omakase dinner at Shinjuku Sushi Makoto – super delicious. It was a small place we got to right when it opened and the fish was amazing and staff was very friendly. Afterwards we walked around the area by Golden Gai at night and got some mochi doughnuts and played claw games.

August 13th:

Started our first day around 8am walking to and exploring Meiji Jingu shrine in the morning. After spending an hour here, we walked over to Harajuku area & went down Takeshita street. Almost everything wasn’t open yet and it was super dead in the morning so we decided to pivot our day and go over to Senso-Ji temple and explore the Asakusa area. The Senso-Ji temple was awesome and the surrounding area was so cool and super busy. We spent our afternoon exploring the markets lining the streets by Senso-Ji (we both loved this area and all the street foods and shops in the market), got a variety of street food (curry cheese bun – so good, chicken katsu, grilled eel, and ice cream). After this, we took the subway to Akihabara to check out the anime/gaming area. Walked around some arcades and played some games, also went to a 6 story sex shop called “M’s Sex Shop” that was very interesting. It started pouring down rain so we went to spend some time inside at a maid cafe. It was interesting and we did get to see some performances on stage but idk if I would recommend – maybe if you’re planning on ordering a lot of food or if you’re with japanese speakers. It definitely seemed like the people that got the most out of it were groups that spoke Japanese and could interact with the waitresses more. We also had to wait probably around 30 minutes to get a table but I think you can also make reservations beforehand. After having a drink there, we walked over to where we were going to get ramen for dinner. The place we were planning on going ended up not being open for another 30 minutes so we popped into a small brewery nearby. The place was super cool and had a bunch of Sake IPAs that were awesome. We started a conversation with some locals at the bar, and asked if they knew of the ramen place around the corner and if it was good. Their reactions made it seem like it wasn’t the best spot, and told us of a different ramen place that specialized in duck ramen they would recommend. Ended up walking over to Ueno area to eat at their recommendation “Ramen Kamo to Negi”. So so glad they told us about this spot – it was one of my favorite dishes we ate the entire trip and definitely a popular local spot. After dinner, we walked through a night market in Ueno, got some dessert, and then headed back to our hotel at the end of the night.

August 14th:

On our second day, we started a bit later at around 8:30am and took the subway to Tokyo tower. We popped into one of the subway station bakeries on the way for breakfast – egg tarts from the subway station were one of my boyfriends favorite pastries we ate… never know where you’re going to find some of the best stuff lol. Also got a melon ball pastry which seemed to be one of the more popular items we saw everywhere, and this was also tasty and light. When we went to the Tokyo Tower we were debating between buying tickets for the main deck or higher deck and after seeing some mixed reviews we just decided to spend a bit more for the higher deck tickets. I’m definitely glad we did because I feel like the view was way more expansive from the top and it was a beautiful view. Luckily we got there about 30 minutes before it started pouring rain and fog encompassed the city so you couldn’t see much of the view after. Overall I would definitely highly recommend the Tokyo Tower because it was an incredible view but we didn’t go to other viewpoints in the city so can’t speak to whether those would be better. After the Tokyo Tower we went to check out the Roppongi area and it was still raining a lot so we checked out Roppongi Hills. Overall we were both very underwhelmed by the mall and wouldn’t recommend going there if you are debating adding to your itinerary – I personally thought it was suuuper overhyped for what it was. However, neither of us are huge luxury shoppers so I can maybe see the appeal if you are into that. We got lunch at one of the restaurants inside. It was funny because we asked one of the local couples inside what they would recommend off the menu and they pointed to something that wasn’t on the english menu but only the japanese one which was soba noodles and hot broth with meat for dipping the noodles. We both ordered this and were super happy with it, it was delicious. After lunch we walked around more in the Roppongi area, got some ice cream, and went to the Tokyo Midtown mall since we were right by it. We both liked this mall better than Roppongi Hills and it had a pretty outside area as well. After this we went back to our hotel and my boyfriend took a nap while I went out and walked around the Shinjuku area more. Got to walk through the main shopping area and pop into some places, check out the Godzilla street, and get to know the area a bit more. At night we had a food tour planned through Trip Advisor that was in the shinjuku area. After freshening up we walked over from our hotel to meet the group at 5pm and our tour guide took us to a few different spots. First place was Tonkatsu Nimura and definitely recommend the pork katsu here – it was super juicy and crispy and good. After this, we went to a spot for Okonomiyaki (can’t remember the name of it but also super tasty), and then next was Takamaru Sengyoten 4 which our guide told us was the best spot for super fresh fish because they got it fresh from the fish market every morning. Got a variety of sashimi dishes here which were all super delicious along with some various appetizers. Our last stop of the tour was this restaurant that made the most amaaaazing soup gyoza. This restaurant somehow figured out a way to make a cripsy pan fried gyoza filled with soup and meat, and it was so good. My boyfriend said it was one of if maybe not his favorite thing we ate in Japan. Both of us were so mad at ourselves because we forgot to jot down the name so not sure what it’s called. After we finished the tour at 9pm, me and my boyfriend decided to check out some bars in the Golden Gai area. Most all of the bars here only fit around 5-10 people total and it took a while for us to find one that wasn’t either completely empty or completely full that looked fun to go in. Ended up in one with a few other people and made friends with some locals and some other tourists so definitely was a good time. I was a little bit intimidated to go in some at first feeling like the locals might be annoyed of the tourists since they were all such small settings, but a lot of them do have signs that are no cover charge for tourists which means they’re typically more welcoming or some have signs stating locals only so just avoid those and you’re good. We ended our night around 11:30pm and while we were walking back to our hotel we got to see some of the nightlife going on in shinjuku which was very interesting.

August 15th:

On this day we were moving hotels, so we spent the morning packing up and heading to Shibuya to drop our stuff off. All the activity and staying out late the night before also caught up to us so got a bit of a later start to the day, and were mildly hungover. After dropping our stuff off, we ended up randomly walking into one of the casinos since we had seen so many in Tokyo and they’re kind of mesmerizing. We decided to try playing one of the Pachinko games even though it was all in Japanese and we had no idea what we were doing. One of the women working there motioned to us how to use it so we started playing, and then every once in awhile one of the locals walking by would motion something else we needed to be doing while we were playing haha. The entire time we didn’t know really what was happening or how much we were winning, but we put 1000 yen in, and ended up winning 22,000 yen (around $150). We kept trying to leave throughout but didn’t know how to stop the machine and whenever we would ask the worker she would signal that we still had a lot more credits to keep playing and she didn’t speak english, but finally we got the point across that we needed to leave because we didn’t want to spend hours here after we kept winning (after we cashed out and realized we had just won $150 I definitely regretted not staying a bit longer and it made sense why everyone was looking at us like we were crazy for leaving…) Regardless of winning money, I would definitely recommend just checking out one of the casinos out and playing a game or two – the machine was so different from anything I’d experienced and got me hooked in. It was a bit intimidating going in when there were no tourists and everything was in Japanese, but people seemed very entertained to see us trying to play and were happy to lend their help. After leaving the casino, we walked over to Shibuya crossing which was really cool to see – definitely recommend. From there, we made our way to Harajuku and explored a lot of the streets on the way over as well. We walked along cat street to get there which I thought was a cute nice shopping street, and then Omotesando area which was also a super nice wide street lined with a bunch of luxury stores – kind of gave me rodeo drive vibes. We ended up doing a light 7/11 lunch since we wanted to try the famous egg sandwiches, and we just got an assortment of food including the egg sandwich along with some sushi and hot food. My boyfriend loved the sandwich but I thought it was ok – I’m not a huge egg salad person but if you are then you’d prob like it. We also got some Takoyaki from a street vendor. We were wondering if we should have tried it again from a different place because the one we got was very slimy and not crispy so I’m not sure if that is typical or maybe it would have been better from somewhere else. Then we went and explored the Laforet Harajuku shopping center which I loved!! Every floor was filled with different very unique clothing and accessories stores, and it was definitely the place I felt like showcased the typical harajuku fashion the most, and had a bunch of cool streetwear stores as well. It was also really cool to see the people shopping there wearing really interesting outfits. We spent probably around an hour exploring here and also popped into Tokyu Plaza Omotesando Harajuku to see the kaleidoscope mirror view which I thought was cool, but we didn’t really spend much time inside as it was more of a typical shopping center. After this, we went over to Takeshita street and it was super busy by around 3:30pm. We got some street food – I got one of the korean cheese dogs which I loved (but I do love anything stuffed with cheese). The place I got it from also sold the cheese filled yens which I tried later on in our trip and I definitely preferred the cheese dog over it – way more flavorful and cheesy. I also tried some candied strawberries on a stick that were super good. I later on tried candied grapes which were not nearly as good imo, and also got candied pineapple which was my favorite but I got this in Korea and didn’t seem like it was as common to find. After spending a while exploring Takeshita street, we went to the Kiddy Land toystore which I thought was a bit underwhelming. Again, me and my boyfriend aren’t big shoppers on trips so it was more browsing for us and we were just tired and hot by this point in the day so maybe I would have liked it more if my feet weren’t dying lol. After this, we walked back to our hotel in the Shibuya area and checked in. After resting for about an hour, we went up to the bar at our hotel to grab a drink before dinner and it was one of the hidden gems we found. It was a super nice bar that was pretty empty when we were there, but the view of the Tokyo skyline was absolutely amazing and it had a really good vibe. It was the bar at the top of the Cerulean Tower hotel – I think it was called Bellovisto. We regretted not making our dinner reservation later so we could have spent more time here as it was getting dark and the skyline was lighting up. After this, we headed to dinner at Kyoto Hyoto Shabu Shabu where my boyfriend had made a reservation earlier that week. We got the “beef and pork dashi-shabu course” which came with an assortment of small plates like sesame tofu (I loved this), boiled hamo, steamed custard with shark fin sauce, along with the beef and pork for the shabu shabu, and matcha pudding for dessert. This was one of our pricer meals but I thought it was worth it, everything was delicious. After dinner we were walking around Shibuya and it started absolutely pouring so we went inside a few different bars. We ended up at a small one called “Rock Bar” and it was awesome! The owner was super friendly and made us super good highballs that were his specialty, and there were a bunch of regulars there that were super excited to talk to us and we had a great time here. We were there until around 12:30am and then headed home for the night.

August 16th:

Got a later start on this day as well due to our late night the day before. We had another tour booked at the Tsukiji market at 11:30am, so we took the subway to the ginza area and headed over to the market. The tour was around 2 hours and it was really interesting to get to explore the market. Our tour didn’t include food, so after it was over we explored on our own. We ended up getting a variety of fresh fish and got to try toro, umi, and salmon. All the fish was so fresh and literally melted in your mouth – so good. We also got a wagyu beef skewer that was so good, along with some fresh melon, and strawberry and chocolate mochi with strawberries in them. This was a super common dessert we saw a bunch and I wished we had tried it earlier because it was so good I wanted the chance to eat more of it lol. We also bought some stuff to take home like wasabi and plum sesame seeds, and green tea. After the market, our original plan was to go to the imperial palace but then we realized it closed at 3:30pm which would only give us about an hour. We also were a bit of a walk from there and it had started raining, so we decided to change our plans. We ducked into one of the cafes in ginza to wait out the rain for a bit and figure out our game plan, and then decided to check out the art aquarium museum. I personally really loved the art aquarium! Initially when we had been planning our trip I wanted to go to teamlabs since that seems like everyones top must do, but we didn’t book tickets in time and all the early times in the day sold out and I was just too stressed about planning our days around a later time in the day. I was definitely bummed about it, but after we went to the art aquarium museum I felt like what we had seen was just as cool as what teamlabs would have been (maybe thats wrong but thats how I felt lol). There were so many unique art exhibitions with the fish, and I was honestly surprised that it wasn’t a more talked about spot for tourists. After the aquarium we checked out the big ginza shopping streets, and were a bit underwhelmed. Just seemed like a ton of luxury shops in kind of a stale area. It was still raining quite a bit, so we decided to go back to our hotel and chill for a bit before dinner. One of the things on my boyfriends must try food list was japanese curry, so we ended up going to dinner at a katsu curry place called Joto Curry. It was a super casual smaller place with vending machine tickets to order, but it was super tasty. The curry had a ton of spices and the katsu was juicy and delicious. After dinner, we walked more around the area near shibuya crossing with restaurants and bars, and we got some ice cream while walking around and watching some street performers.

August 17th:

This was a travel day from Tokyo to Kyoto. We packed up our stuff and headed to the train station where we were going to take one of the trains with our JR pass to Kyoto. It definitely took more time to get to the station and to a train than we had expected. We decided to get a bunch of food for lunch from the places in the station and eat on the train, so we got a spread of a beef bento box, sushi platter, and 3 different veggie/salad sides and some pastries. The day we were traveling was right after there was a typhoon near the area, so there were a bunch of train delays and the station was pretty hectic. We got super confused on whether we needed to book seats for a train or if we could just get on because we had the JR pass. We tried booking seats with the pass at the station, but then said the next available seats were on a train that wasn’t for a few hours so we decided to just go without reserved seats and the unreserved area on the train was packed so we standed for a while of the ride and then eventually got seats. We arrived to our hotel in Kyoto around 3:30pm. It was later than I expected, so I wanted to go to Fushimi Inari that day since it was a bit out of the way from the other sites I wanted to see. so it seemed better to just dedicate the rest of our afternoon to it. We took the subway to get there and arrived around 4:30pm. We took our time exploring more near the bottom, and then started hiking up the path. I did not realize how long the hike would be, so by the end we were basically racing to the top to finish before the sun went down (I had seen that there are wild boar that come out at night and didn’t want to experience that lol). We got to the top completely drenched in sweat and then got to see the sunset when we were coming on the way down. Idk if its the time we went or because not a lot of people go all the way up, but when we were near the top and coming down it was so much more empty and you could walk for a while without seeing anyone which was nice since when we first got there it was basically just walking squeezed with a bunch of other people. We finished around 6:30 and then headed to our hotel to shower then went to dinner. I was super tired on this day so we just went to a BBQ place nearby our hotel called Yamadaruma. My boyfriend really liked it but fatty meat can make me feel sick so I didn’t eat a ton here. Got some ice cream and walked around, then headed to our hotel for the night.

August 18th:

This was our only full day in Kyoto, so my itinerary was definitely more ambitious than what we actually got to do. I had a ton of stuff on the list and we got to probably around half, but I still felt like we got to see a lot so I was happy with it. We started our day walking through the city to get to Kiyomizu-dera temple and got there around 9:30. It was beautiful up there, especially walking on the path and getting to see the view of the temple in the greenery with the city in the back. We spent about 45 minutes here and then I realized we had way less time before our lunch reservation than I thought we would. We walked through Ninenzaka and Sannenzaka on our way to get to Kodai-Ji and the streets were really cool and looked full of yummy food – I was sad we couldn’t spend more time here and eat here, so we ended up walking back through later in the day. We had to rush through Kodai-Ji and then hurry to get to our lunch reservation at 11:30am which was a traditional Kaiseki lunch at Kikunoi Roan. This lunch was super interesting with super fresh seafood and vegetables, some which were only local to Kyoto, and I’m really glad that we did it. Some of the courses definitely pushed me out of my comfort zone, and others were some of the best dishes of our trip. Definitely would recommend doing a traditional kaiseki because we both really enjoyed the experience. After lunch my boyfriend was a bit temple-ed out, so we decided to spend time exploring the city and going through the Nishiki Market. We spent about 2 hours here, and then headed to Yasaka Shrine. We both really liked this spot and there was a lot to explore around it. It was also way less crowded than the other places we saw and a lot more peaceful which was nice. After spending about an hour here, we walked back through Ninenzaka and Sannenzaka area but were pretty tired by this point in the day. Afterwards we walked back to our hotel for a while before going out for dinner. We went to get ramen at Ramen Miyako – Gion, but we both thought it was pretty meh. My boyfriend had found it while doing research on top spots before the trip, and it was definitely very much a tourist spot. We realized that the places that were on those food lists most times had worse food than the spots we would just stumble upon or hear about from people in the area. Maybe this was just our experience, but I would say I would definitely recommend being open to just finding restaurants on the fly. We also found that all of our favorite places typically had some of the lowest ratings on google reviews so just be weary when looking at those. After dinner we walked around the Gion/Pontocho areas and loved going down the alleyways here at night. Definitely also a way bigger nightlife scene than we were expecting, but it was Friday night so it was pretty busy. We walked around the area for about an hour and half and got some dessert then headed back to our hotel for the night.

August 19th:

We decided to leave straight for Osaka in the morning, so we took a JR train from the main station and got to Osaka around 11:30am. We dropped off our stuff at our hotel, and headed out to explore the Dotonburi area where we were staying at. We were pretty hungry and were going to head to a soba noodle place that someone had recommended us, but then realized they were closed on saturdays. We just went into one of the first places we saw, which was a dumpling place that was pretty good. After lunch, we walked some more and went over to America-Mura which I thought was one of the more unique areas to check out. It was really cool to see all the stores with “western” style clothing with a japanese take on it, and just felt like a really cool and hip area. We checked out a mall here and saw a brief j-pop performance inside, and played some pinball at an arcade. After looking in some more stores, we headed to our hotel to check in and rest a bit before the tour we had planned that night. We booked an “off the beaten path” sake/food tour through airbnb, and it was definitely one of the biggest highlights of our trip. We weren’t sure what to expect, but our guide grew up in the Kita area where the tour was, so it truly was off the beaten path. Our guide Taka was amazing and really made the tour so much fun, and all of the places he took us we definitely would not have been able to go on our own and they were all super special. One of them was a bar that was actually in a liquor store, and they had the best sake I’ve ever tried. We tried a bunch of different popular Osaka dishes including octopus, tofu, fish, veggie, beef, and tempura dishes as we hopped around to 3 different places. We also were with a super fun group of people, so after the tour was over we all went to a karaoke bar that our guide took us to which you paid by the hour and also got unlimited drinks during your time there. Definitely took advantage of that lol. We all went out bar hopping afterwards and after too many drinks we decided to go home.

August 20th:

This was our last day in Japan before leaving, but we were so hungover from the night before. Our entire trip we were cognisant of the fact that we wanted to experience the nightlife but avoid drinking too much to affect us the next day, but we felt like that one night in Osaka it was worth it. I think the exhaustion from the trip was also hitting so we ended up sleeping until like 12:30pm and got a very late start to the day. We were planning on going to a noodle place that our tour guide had recommended, but when we got there they were already closed (30 min before their listed closing time – we realized that was more common there so definitely be careful of trying to go somewhere too close to closing). We ended up going to a Katsudon place by Sennichimae Doguyasi shopping street called “Katsudon Yoshibei Namba Doguyasuji”. We got a couple of different dishes that were all delicious, and the lady who was serving us and cooking was so nice! She even added a smiley face of hoisin on our katsu. Afterwards, we walked a bit around the area and then headed to the Osaka aquarium. I’m not a huge fan of aquariums, but I had heard this one was supposed to be awesome, so we decided to go. We bought tickets online right before we went in, and they had signs up that buying tickets at the stand had a line wait time of 75 minutes to get in and buying online had a wait time of 45 minutes, but we didn’t end up waiting at all. The aquarium definitely met if not exceeded my expectations, and I really enjoyed it. They have whale sharks which were awesome, and a ton of different sea creatures that were really cool. After the aquarium we went on the ferris wheel right by, but a lightning storm started right after we got on so we spent the entire 15 minutes going around terrified haha. After the ferris wheel, we took a subway back to the Dotonburi area where we were going to get sushi at a spot my boyfriend had found online. When we got there, they were closed because they had already sold out for the day. We ended up going to a random spot right across the street which ended up having some of my favorite sushi and sashimi of the trip. It was so good and so well priced (unfortunately didn’t write down the name). Afterwards, we also got a cheese yen, oreo churro ice cream, and some egg tarts, and went to walk along the riverwalk and eat our desserts. We spent the rest of the night walking around the riverwalk area and sitting on a bench reminiscing about our time in Japan. We went back to our hotel at the end of the night and then got ready to fly out the next morning.

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