After a whirlwind five days at home, I was off on my second trip, this time to Asia (Japan and Singapore). I had never been to either country and visiting Japan during cherry blossom season sounded like a magical experience. My friend Lauren had also been wanting to visit Japan for quite some time, and I was thrilled that she was able to join for my entire 15 day itinerary (based off my friend Heather’s itinerary, with slight modifications).

We started our trip off with three nights in Tokyo. As soon as I started to research things to do in Tokyo, I realized that there was no way that three days was going to be enough time. I also realized that this was a city that I’d want to return to again and again. We didn’t want to cut anything out of our larger Japan itinerary, so I decided to prioritize some key activities for trip #1 and vowed to return.

The Flight

I researched peak times for cherry blossom season in Tokyo and settled on an arrival date of March 28th. We of course flew on Delta (through Detroit) to Narita airport on one of their Airbus A350s. Planning for unemployment when booking the flight, I opted to not splurge on a Delta One Suite, and instead try their newish Premium Select class. Premium Select is supposed to be a step up from Comfort+, but obviously doesn’t have all the perks of Business class (i.e. flat-bed seats). I felt a twinge of regret boarding the flight and gazing at the suites up front, but reminded myself that I’d get to enjoy a suite on my return flight from Singapore (which would include an extra connection in Seoul, operated by Korean Air). My frugal tendencies had their limits.

As I frequently fly solo, it is always nice to have a friend along to share the more mundane experiences of travel with (traffic, lines, basically anything that involves waiting). I recalled why I don’t like flying Delta out of EWR, as their security does not yet offer Clear and their TSA pre-check situation leaves a lot to be desired (you can keep your shoes on, but you get merged with everyone else and still need to remove larger electronics from your carry-on bags). Thankfully, I have no other flights booked out of EWR the rest of the year.

Lauren had brought along Kirkland brand OTC sleeping pills that her mom gave her. I typically don’t like to take any kind of sleeping meds when flying, but we were leaving Newark at 9:35am and scheduled to arrive at Narita at 2:45pm after nearly 16 hours of travel (it ended up being 22 hours door to door). If I wanted to sleep enough on this flight to be able to stay awake until a reasonable hour in Tokyo, I’d need some help. Lauren assured me that the pills worked well and that she had never experienced any side effects, so I decided to try one.

Game changer. Why had I waited so long to try this? The Costco-bought sleep aid supposedly has the same active ingredients as Unisom Sleep Tabs, which I will be purchasing immediately upon my return to the States. My first experience in Premium Select was quite comfortable, and I slept nearly seven hours. Things I liked about Premium Select: you are offered a welcome beverage pre-departure (I opted for sparkling wine), the seats are in a 2-4-2 configuration (vs. a 3-3-3 configuration in the Main Cabin; I was seated in 21B, so I only had one seat-mate) and the seats are roomier than in the Main Cabin and also provide a footrest. The meal service didn’t seem too different than what you’d get in the Main Cabin, although the flight attendants did set a white placemat down beneath our trays, so at least the appearance was a little nicer.

Anyway, the flight was on time, Lauren and I both slept a good amount, turbulence was minimal and our checked luggage made it to Narita. No complaints.

Day 1: Falling in Love with the Park Hyatt

The immigration line was relatively long, but also moved rather quickly (it took us about 30 minutes to get through immigration and customs). The shitty part about flying into Narita is that it’s not close to the city of Tokyo, and all transit options take 90-120 minutes door-to-door. Lauren and I wanted to look into getting our JR passes at the airport (we already had our vouchers), but after entering the queue at the JR kiosk, we were told it would take 30 minutes and that we’d still need to go to the JR office at Tokyo station if we wanted to change the activation date to 3/28 (which we did want to do). At that point, we had missed the 3:45 limousine bus and the next one to Shinjuku wasn’t for another hour. We also didn’t want to deal with a train that would require a transfer or two with all our luggage. So, we decided to just throw money at the problem and got ourselves a taxi for the bargain price of 29,000 yen ($260)!

Then we of course ran into a bunch of traffic once we neared the city, so it took us nearly two hours to get to our hotel.

I had chosen the Park Hyatt for our three night stay in Tokyo. The hotel is particularly famous for its role in the film Lost in Translation, where many of the scenes were shot. It is also consistently rated one of Tokyo’s top hotels, and I was able to transfer Chase points to Hyatt’s rewards program, redeeming for a stay for a $1000+/night room that would cost me $0 in cash. It was an easy decision.

Our taxi finally pulled into the Park Hyatt and we received a warm welcome from a bubbly and enthusiastic Japanese woman. She dropped our bags off with the bellman, then led the way up to reception on the 41st floor. We checked in and were then led to our room on the 50th floor. The hotel was absolutely beautiful: understated, elegant, modern design with lots of marble, wood and glass. I appreciated the pale green color scheme, which was much more interesting than the “greige” shade that many luxury hotels use, yet still tasteful.

Despite my Explorist status, Hyatt was not able to offer an upgrade due to the high capacity at the hotel. Not a big deal, as our Park room was still incredible. 

We were worn out from the long flight and the thirteen hour time difference, but knew we had to keep ourselves awake until a reasonable bedtime hour. Our plan was to freshen up and then hit the New York Bar on the 52nd floor for some cocktails and a snack. After a very welcome shower and a change of clothes, it was time to hit the bar. Oh, we also had to spend a few minutes playing with the fancy, high-tech toilet – little did we know that going to the bathroom in Japan was going to be a cultural experience itself.

I absolutely recognized the bar from Lost in Translation and was delighted when the jazz band came out to perform (sadly, the singer was not the same woman that Bill Murray’s character had a one night stand with in the film).

We ordered some crudité, as the bar menu was very meat-heavy, a challenge I would continually run into throughout Japan. Then we chatted with the attractive (but married) Swedish men sitting across from us at the communal table. They worked in the theme park industry (definitely the first time I had met anyone that could claim that) and were on a boondoggle of a business trip to Tokyo, including a dinner that cost $1,000/person. Hmm, should I consider a future working in theme parks? Not sure I could swing that kind of pivot, but they seemed to be doing something right.

We finally made it to 10pm and headed back down to our room. While getting ready for bed, Lauren had the bright idea to look for a food tour through Airbnb Experiences the following night since we hadn’t yet made dinner reservations. We were both feeling a little intimidated by the city and figured a tour would be a great way to ease into our first night out.

Day Two: Meiji Shrine, Yoyogi Park, Harajuku, Shibuya Crossing, Meguro River, Ueno Food & Bar Crawl

We woke up early and eager to explore Tokyo on our first full day in Japan. After hitting the very well-equipped and sizable gym and enjoying very tiny, over-priced egg white omelets for breakfast, we were finally out the door of the Park Hyatt. Although it wouldn’t have been a bad place to stay a bit longer, we had things to see and do.

First up was the Meiji Shrine and Yoyogi Park. Located within a 20 minute walk from the hotel, it made the most sense for us to go by foot. I think the best way to see a city is by walking (most cities, that is), and Lauren agreed.

After traveling through South America with guides most of the time, I found myself wishing that I knew more about some of the sights I was seeing, but it was also nice to do things at our own pace.

Harajuku borders one side of Yoyogi Park, so we kept walking after seeing the shrine and the park. Harajuku is known for being a hot spot for Japanese youth culture and fashion. It also features a large number of animal cafes, where people can pay to spend 30 minutes or an hour petting and playing with various types of animals. I believe this started with cat cafes, but has since expanded to shiba inu cafes, owl cafes, and our choice: a hedgehog cafe. 

While I got a thrill from the novelty of the experience, I was glad that we had opted for the 30 minute option and not the full hour. The hedgehogs did not seem too excited about being held (the one that was handed to me kept squirming and seemed really uncomfortable). I didn’t want to drop the poor thing and I also didn’t want to touch the “dangerous” nose. Then he (?) pooped on my glove, so that was the last straw. After a couple minutes, I set him back down in his cage where he promptly fell fast asleep.

After our 30 minute session concluded, we were hungry and found a gyoza restaurant nearby that had high ratings on Foursquare (yes, I sometimes use Foursquare for recommendations when traveling internationally). I was pleased to see that my brother had also issued his stamp of approval in the app. When we reached Harajuku Gyoza Lou, we found a line outside, which seemed to be another indication that it was a worthy spot. I usually don’t like waiting in line to eat or drink, but we decided to queue and see how quickly things moved.

About 15-20 minutes later, we were brought to a small table in the back of the restaurant, next to two other tables of tourists. As I had ascertained from the Foursquare reviews, the menu did not include any vegetarian gyoza, but I hoped there would be some other good veg-friendly options.

Lauren did enjoy the meat dumplings, although she had no idea what kind of meat they contained (pork?). The group of Americans next to us ordered beers and hot sake, so we decided to follow suit. 

The service was iffy, but we eventually got everything that we ordered and enjoyed the opportunity to rest our feet. We started talking to the foursome next to us; they were all American Airlines flight attendants in their 20s and living in Chicago. They had also booked some Airbnb Experiences and one girl offered up a bunch of recommendations for other destinations on our itinerary.

Next up was Shibuya Crossing, which we again decided to walk to. After a charming stroll through Harajuku, we arrived at the famous intersection (it is supposedly the world’s busiest pedestrian crossing). It was early in the afternoon, so it was not as crowded as it would be at peak rush hour, but we still got to experience the concept. I laughed at how I typically try to avoid crowds and used to constantly complain about all the tourists when I worked in Times Square, but now that I was in Japan, I actively sought out the busiest intersection in the most populated city in the world. We first walked the crossing ourselves, then headed to the viewpoint at Mags Park to watch the event unfold a few times below. We’d watch the cars take their turns from various directions (including numerous go-karts, always driven by people wearing ridiculous furry-type costumes). Then, the last cars would pass and suddenly all of the pedestrian walkways would be swarmed with people.

At that point, it wasn’t even 3pm and we didn’t need to be in Ueno until 7pm, so we decided to check off one more item on our list: the Meguro River to see the cherry blossoms. It was a bit of a walk, but we didn’t mind. I wasn’t really sure what to expect, but had read that the Meguro River was a top place in Tokyo for cherry blossom-viewing. Once we hit the river (it really wasn’t much of a river), we saw rows of cherry blossom trees for blocks and swarms of people strolling along the banks. 

There were numerous stands set up selling all sorts of snacks (lots of fried food), beer, hot sake and of course, a ton of pink champagne. We opted for a strange (but hot) unfiltered rice wine beverage to warm us up. I also ordered a baked sweet potato (unfortunately, no toppings like an American loaded baked potato) to supplement my lunch of cucumbers and cabbage.

After about 30 minutes of ambling along with the celebratory crowd, we decided to find our way to Ueno. It would be our first time taking the Tokyo subway, so we wanted to leave a buffer in case of any mishaps, and we were also thinking it would be nice to find a retail store selling some kind of extra layer to keep us warm.

At the Meguro subway station, Lauren found a very friendly subway worker to help us buy our IC cards, which we pre-loaded with yen so we wouldn’t need to keep buying individual tickets. It was a bit confusing at first, but we quickly developed a strong respect for the Tokyo subway system. Compared to the New York subway, it was extremely clean, dependable and simple to navigate. All the platforms, stops, station exits and entrances were numbered, and Google Maps could tell us exactly where we needed to go, and when. On top of that, the trains came frequently and were on time. Always. At one point during our stay, we needed to use the bathroom, and we decided to check out the situation at the subway station. To our amazement, it was perfectly clean and sanitary. I would never even consider using a NYC subway station bathroom (in fact, I’m not sure if they even exist).

We made it to the Ueno station with no issues and a couple hours to spare. I was ready to rest my feet and enjoy a hot beverage, so we found a cafe/diner where we were for sure the only white people. 

Next, we endeavored on a quest to find some warmer clothing (silly us; we had both just brought leather jackets, thinking it wouldn’t feel as cold as it did). Lauren identified a Uniqlo shop in the Ueno station, so we decided to head back there. Long story, but after 45 minutes of walking all over and around the station, asking for directions and walking some more, we left Uniqlo with a hoodie (me) and a heat-tech under-layer (Lauren). Success, kind of.

Finally, time for the food and bar crawl to begin. We met our guide, Akira (Aki for short) outside of Starbucks, along with two of our other eating and drinking buddies: Justin and Kyle from Boston. They both worked at the tech company Hubspot and Kyle was enjoying a mandatory month-long sabbatical imposed by the company after hitting his five year mark. He obviously wasn’t complaining about it.

Aki explained that we would be making four stops throughout the three-hour-long event. The first stop was a lively seafood restaurant where we had to take off our shoes before climbing into the booth built into the ground.

Our final two tour participants, Dmitri and Joseph, finally joined us (they had just arrived in Tokyo from San Francisco, and had of course gotten stuck in traffic). At one point, the Japanese girls seated next to us all started shrieking hysterically and jumped up on their booth. Apparently one of them had found a giant spider in her purse. Oh, great. Just what we needed to hear while our bare feet were dangling into a dark hole in the ground.

The second stop was a casual, crowded, smoke-filled restaurant known for its pork. Aki wouldn’t elaborate on what exactly he was going to order, but he kept describing it as pork “meat,” with air quotes, which everyone found very assuring. I was happy to pull the pescatarian card at this place. After the rest of the crew had tried the four different kinds of pork, Aki finally explained what it was: heart, liver and gizzard in addition to a more standard cut of meat. We also tried some pickled plum, which is apparently a Japanese delicacy. I deemed the sour, fermented flavor to be an acquired taste that I wouldn’t be attempting to acquire on this trip.

Next up was a stand-up bar, which is essentially just a bar that is standing room only. 

Aki ordered us some very refreshing drinks on ice that Lauren and I liked so much that we ordered a second round. The stand-up bar was the most entertaining event of the evening. Immediately upon arrival, Kyle befriended an inebriated yet jolly Japanese man in a Supreme hat and a camo jacket. He didn’t speak English fluently, but spoke well enough to realize that Kyle was his long lost brother from another mother. We spent the next 30 minutes watching the two of them joyously bond while the rest of us couldn’t stop laughing.

Sadly, Kyle and his new best friend had to part ways, so we could make it to our final destination for ramen. There was a short line for the small counter at the restaurant by the Ueno station, so we filed in a couple people at a time. Aki helped us to place our orders from a machine on the wall that looked like a cross between a jukebox and a vending machine; I opted for what was called dipping noodles since I wanted something vegetarian. You essentially dip the noodles into broth with chopsticks, and then eat it. I am pretty sure that the broth was still meat-based, but oh well… when in Japan.

Aki bid us farewell and Dmitri and Joseph treated Lauren and me to a final glass of wine at the Spanish restaurant next door. We had been fronting them yen all evening (in exchange for USD) since they hadn’t yet gotten yen and didn’t realize that many places in Japan are cash only (c’mon, do your research). At that point it was nearly 11:30pm and we were tired, so we decided to try our first Uber experience back to the Park Hyatt. Japan only offers Uber Black, so it was expensive and it took about 10 minutes to arrive, but at least we could pay by card and it was a quick and comfortable ride at that time of night. 

Day Three: Senso-ji Temple, Ueno Park, Imperial Palace, Bar Benfiddich, Shirosaka

We had another ambitious agenda for our last full day in Tokyo. I woke up early and couldn’t go back to sleep, so I decided to hit the fantastic Park Hyatt gym again. I was really falling in love with the place. 

Our plan was to start at the Senso-ji Temple, a famous Buddhist temple located in Asakusa. It was way too far to walk, so we got to use our IC cards and take the subway again. Walking to the temple, we stumbled across Orange Street, a street full of shops that is literally painted orange. 

We finally arrived at the entrance to the large red temple that was swarmed with tourists and smoke. Lauren in particular was very impressed with the site as it was her first visit to a Buddhist temple in Asia.

After snapping a bunch of pictures, Lauren decided to ask one of the workers what the deal was with all of the incense and smoke. Apparently, people would pay for some incense, light it, stick it into a large fire pit of sorts, and then waft the smoke toward them to purify themselves. Purification couldn’t hurt, so why not try it?

We then joined the mass of people slowly walking upstairs into the temple, where we could make an offering. 

One of the good things about traveling with Lauren is that she will make friends anywhere she goes. She had read that you could make a wish at the temple and was curious about how the process worked, so she started chatting with a local named Cody that spoke perfect English (turns out he lives in LA for part of the year). Cody ended up walking with us to show us what to do. Essentially, you make an offering of 100 yen, gently shake a wooden box of sticks, ease a stick out of a small hole in the top of the box and then find the drawer with the characters that match the characters on your chosen stick. You then open the drawer and pull out a piece of paper with your fortune.

We said “arigato” to Cody, bid farewell to the temple and headed on our way. Lauren wanted to buy a knife at a famous knife store nearby, so we went there next. They were very friendly and helpful, and even engraved her knife with her name in Japanese characters on the spot.

Our next stop was Ueno Park, which we had heard was a great place to view the sakura, or cherry blossoms. We were able to walk, and we arrived to a huge mass of people exiting Ueno Station and entering the park, so we just followed them.

The sight that greeted us at Ueno Park was unlike anything I’d ever seen before. The lanes between the blossoming cherry trees were lined with picnic blanket after picnic blanket (actually more like durable blue tarps) and groups of people seated around their picnic spreads, all with their shoes removed. The food options appeared to range in complexity (some were quite impressive), and everyone was drinking. The mood was jovial and festive; some people were wearing costumes and playing music. Officially called “hanami” in Japan, this essentially translates to the ephemeral act of enjoying the seasonal flower blooms, and the Japanese clearly take it very seriously. I don’t know why we don’t have a similar tradition in the US, but we should.

We stumbled upon a geisha performance and stopped to watch a couple rounds. The first was a group of eight women, who displayed all of the intricate steps involved in tying the massive bow behind their backs (all from memory, all in unison as music played in the background). It must have taken a lot of practice.

Then we grabbed some beers and French fries (seriously, the longest fries I have ever seen in my life, but also pretty bland; unfortunately, the non-meat options were extremely limited at all of the food stands). As much fun as the atmosphere was at Ueno Park, we wanted to make it to the Imperial Palace before it closed at 5pm (according to Google). So, we made our way out of the park and toward the subway again.

Despite arriving at the Imperial Palace at 4:15, we were turned away at the entrance and told that the grounds actually closed at 4pm. Damn you, Google! 

This is when the efficient Tokyo subway system backfired on us. Google Maps was instructing us to use a very specific entrance to the station, so we walked in circles for a while, but could not find the recommended entrance. Finally, we just chose an entrance and were still able to get to the platform we needed. Good to know that the entrance listing was just a suggestion, not a requirement.

Back at the Park Hyatt, we rested for a bit, then changed and jumped in an Uber. While I had a long list of bars that I wanted to see in Japan, the one at the top of my list was Bar Benfiddich, a dark, cozy bar in Shinjuku that was currently #49 on the World’s 50 Best List (I would not make it to the other Tokyo bar on the list, High Five… will have to do that on my next trip). We could have easily walked from the Park Hyatt, but it was cold, our feet were tired and it was starting to rain.

We were greeted at the entrance of Bar Benfiddich by the owner, Hiroyasu Kayama. He informed us that they had a guest bartender that night and were fully booked, but could accommodate us if we returned after 8pm. Well, that wasn’t going to work because our dinner reservations were for 8:30pm. Peeking inside the bar, we saw that tables were still available, so we started to negotiate. “Can we just wait here for a few minutes? What if somebody doesn’t show up? Is there anywhere we can squeeze in for one drink?” He stood his ground at first, but finally relented and showed us to a small booth in the corner. I could accept the worst seat in the house; I had no idea that reservations were required.

Despite the fact that the bar was featuring a guest bartender, Hiro offered to make us drinks of his own style. Bar Benfiddich does not have a menu, so we just told Hiro what we liked and he went off to create our concoctions. I ended up with a stirred coffee cocktail and Lauren received a complex, herbaly, citrusy whisky drink on the rocks. Hiro was quite hospitable once he finally let us in; he asked if we were from New York (hmm, could he tell by our unwillingness to take no for an answer?) and asked if we had been to his friend’s bar Angel’s Share, a speakeasy-style bar in the East Village. We both had, so hopefully that helped to ingratiate ourselves to Hiro a bit more. I told him a little about my brother, showed him the blog post that Jonathan had written about Tokyo bars (Hiro was featured) and talked about visiting Speak Low in Shanghai (another Top 50 bar opened by a Tokyo-born bartender).

The time eventually came for us to head to dinner, so we paid our bill and ordered an Uber. We hadn’t realized how hard it was going to be raining and didn’t have umbrellas with us, so Hiro gifted us with umbrellas from their stash as we departed.

On to our first keiseiki-style dinner of the trip. I had chosen Shirosaka after seeing it on multiple best restaurants lists and validating with excellent reviews. Unfortunately, Saturday night traffic was a bitch with the weather, and we were running late. Knowing how precise the Japanese are, I became anxious, but Lauren called the restaurant to inform them of our transit issues and they said no problem. Phew.

The restaurant offered just one set menu (I had informed them of my special needs diet) and we opted to do the sake and wine pairing. There seemed to be fewer than 20 seats in the entire place, and we were seated at the counter. Everything was very good and I enjoyed the pairings, but I wouldn’t say that anything stood out to me as particularly memorable.

At the end of the meal, a Japanese-American woman living in San Francisco emerged from one of the tables behind us, along with a crew of several others. Their group had been loud and raucous all night, and were clearly having a good time. She leaned over the bar to taste a whisky that she had learned about during the meal, and started to chat with us, inviting us to meet them out for drinks after dinner. I must be getting old, because the idea did not appeal to me at all. I was curious to try the whisky, however.

We wrapped up the evening with a final Uber ride back to the Park Hyatt and settled into our comfortable beds for a good night’s sleep. Our plan was to have a relaxed final morning in Tokyo (one last chance to work out in the Park Hyatt gym!) and figure out how to get our JR passes so we could begin our travels around the rest of the country. The morning was nice and relaxing, but the JR passes proved be be a little more stressful. Why? Read on…