Lindsey Frances Illustration


A First Time Trip to Tokyo, Japan


tokyoguide_towerIMG_6739TokyoTravelGuide_LettersI've been considering for a while now how to write a travel guide from our Tokyo portion of our Japan trip. It seems impossible to me now to describe how much I love Tokyo without the two of us packing up our apartment, selling off all of our possessions, and living full-time in Japan for a few years. Then, only after years living in Tokyo, do I think I could really write an insider's guide. 

But short of moving, I've settled on writing what a first time trip to Tokyo (and then Kyoto to follow) was like for us, how we planned, what we had time to do, etc.

I hope it helps another Japan enamored individual dreaming of their first trip to the land of the rising sun.

Here it goes!

How We Flew to Japan for Cheaper than We Expected

We have both always wanted to go to Japan (I'm talking, teenage dreams here.) but we also feared the long distance flight cost.  Thankfully there are a few tricks to finding that sweet spot travel deal to Asia. The exchange rate right now is also quite favorable, too. 

Sixth months before we started our trip planning by monitoring flights on The Flight Deal. The Flight Deal is my absolutely favorite travel web site. I've scored deals to Paris, Milan, Sweden, and New Orleans all from just reading the daily email.  

After noticing Japan deals posted on the Flight Deal, but not in our preferred time frame given vacation days we already had, we found a flight by using Google Flights. Google Flights is a neat service that helps you target select dates for travel, showing you when prices are higher or lower. Knowing we were in the shoulder season also helped target a price for about $800 round trip per person.

We also opened a travel rewards credit card months before the trip in order to get a signing bonus after reaching a specific amount on the card. If you have good credit and pay your monthly credit card bill on time, opening a card like Barclays Arrival Plus or Chase Sapphire Preferred (this is not sponsored, just my two cents) can significantly help defray costs of a once in a lifetime trip.  With our accumulated points we subtracted almost $800 from our total airfare cost, meaning we paid a little over the cost of one round trip ticket.


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Arriving in Tokyo

We flew first to Hong Kong on a 15 hour flight from New York City on the wonderful Cathay Pacific. This was a great flight, with an attentive crew who made flying economy for such a long distance very comfortable. It turns out this route from Newark to Hong Kong is one of the longest flights in the world! For someone like me it was a specific thrill to overcome as I'm not the most comfortable flyer. There was an abundance of entertainment and snacks--like cup of noodles--for the duration of the entire flight that eased a lot of my long-haul jitters. I even slept for more than a few hours.

At Hong Kong we had a several hour layover before switching to another Cathay Pacific flight to Tokyo's Haneda airport, one of two airports in the Tokyo metro area. We decided on a flight to Haneda over Narita because it is actually closer to the city. I believe that more international flights arrive at Narita, though.

At Haneda we took the airport limo bus into the Shinjuku where we were staying. On the way back (we flew the same route home) we actually took the monorail to the airport. I would definitely recommend the airport limo bus, especially when you're arriving, because it made the process much easier. You can see if it stops at your hotel, or like us, take it to a major train station area.

Where To Stay 

For the two people traveling to Tokyo renting an Airbnb offered the best deal that we could find. However hostels also looked like a fun and easy way to travel on the cheap.

I can't speak exactly to the precise legality of Airbnb in Japan as a whole---a few internet searches suggested it operates on the down low perhaps--but we had no issues with our hosts and apartments. They apartments we rented were neat, compact, and easy to navigate. 

We decided to look in popular area for renting a place, narrowing it down to Shinjuku, Shibuya, or Harajuku. While we stayed in Shinjuku, I'd also recommend the areas around  either as good starting points. 

A big plus to renting an Airbnb was that the host provided a pocket wifi we could take with us as we traveled around the city. I realized after the trip that you can also book pocket wifis at the airport when you arrive. I would recommend getting one for your entire trip, either way. It was beyond helpful to have on us especially when navigating streets and subway systems. 

Though we rented an apartment for most of our stay, the last night in Tokyo we stayed at the boutique business hotel Hotel Niwa. It was a lot bigger than I expected a hotel in a city of tiny spaces to be. It was quite fab, with the rooms decorated like Japanese tea houses. It offered a nice respite on our last day in the city. 


IMG_6929Getting Around 

Train stations are huge and full of things to do, buy, and eat in Tokyo. Shinjuku Station for example is actually made up of multiple department stores, concourse levels, food courts, cafes, and more. All this density makes train stations themselves a destination. I imagine if you had only a night in Tokyo, you could eat everything you dreamed of in a station like Shinjuku.

Tokyo is a sliced by multiple lines of commuter trains and subways, all operated by different private companies. Urban planning wise this system is utterly fascinating. Coming from New York City where everything is run by a single government agency, it was strange that there was no solidified system or plan. There was a hyper intensity to the mix of train lines in Tokyo.

Transit is a complicated economic and political situation for sure,  but I will say the service was so much better compared to New York City's over burdened and oft-delayed subways. 

The JR Yamanote Line is a perfect line to ride because it travels a circle around the city. Since you pay by distance traveled you could even just stay on the train, sightseeing as you go, and end up paying just the cost of the single ride. If you have limited time in Tokyo, I'd stick to this train for most outings.

We didn’t have a JR pass for the entire trip so we bought Suica cards at a station. These cards are transferable to the other lines, which helped when we did transfer from the Yamanote line. 


Making an Itinerary

First off, Tokyo is a megacity of 35 million. Nothing in the United States even compares to it's size, and we're New Yorkers.  That being said, there is way too much to do in Tokyo to fit into a five day trip. I don't think a month would scratch the surface. So we agreed to just do what we could, simply put. I think this was the best strategy though I already have a list of what I'd do if (when) I return.

Before we left we armed ourselves with a handy Lonely Planet travel guide too. I also loved the Hey Kumo blog guide to Tokyo as well as photographer Jack Spicer Adam's video guides from his trip.

It also helped us to bundle things together by area so we could plan a day over breakfast then know what train stations we'd be going to. We used a shared Trello board for each day, too. Traveling is so much better with trello, by the way.

Things to do, What we did 

Get lost in the lights and crowds of Shinjuku, day and night. We loved ending up in an Izakaya in Piss Alley.  You can recognize an Izakaya for their red lanterns, business clad patrons, and yakitori of chicken or pork. Glimpse another side to Tokyo (albeit completely walled off from foreigners) by wandering into the adjoining red light district. I liked to just stand inside Pachinko parlors in awe of the noise. 

Harajuku is perfect for observing the well known street style and culture, but is also full of smaller streets packed with vintage stores, cafes, and boutiques. Takashita Dori and Cat street are prime people watching spots. Also, don’t miss the trendy but delicious cylindrical crepes that this area is known for. (Yes I do want ice cream in my crepe thank you very much.)

Meji Jingu Shrine. It’s near to Harajuku but serene and quiet, even with the crowds. If you’re lucky you’ll catch a Shinto wedding which we did!

Tokyo Metropolitan Building is free and offers a panorama of the city. It's not too far from Shinjuku, either. We went at night to the North Observatory for a gorgeous view. 

Spend a day or night in Shibuya for the famed crossing, for the busy streets. Find the hachiko statue, explore Tokyu Hands (the best, most enigmatic store of everything from leather goods to crafts to tiny scientific models), robotic or conveyor belt sushi, and general entertainment and shopping. Although I love independent non-American chains while traveling, the Starbucks in Shibuya has the best sport for watching the crowds. 

A little outside the hustle of the crossing, Shibuya can be small scale and quiet, full of interesting and trendy cafes and boutiques. We liked Shibuya Booksellers and Fuglen, a Norwegian coffee shop and bar for both day and night. 

Eat at Japanese 711. Enough said. It’s fun, full of weird but delicious edible items. It's mad cheap!

Cheap eats! I blogged about all the cheap and wonderful things you can find and enjoy in Tokyo. Save your cash and eat it all.

Get lost in Tokyo Station for Tokyo Ramen Street and Character Street for delicious fast but beloved ramen and the weirdness of a Tamaguchi or Anime Store respectively.  

Tokyu Hands! I mentioned it already but it’s absolutely addictive, full of everything you think you want. It’s a great place to buy gifts like washi tape. There are multiple locations around the city, too. 

Browse expensive department stores and stop at their food foods in Ginza. Mitsukoshi has a grand food hall and open roof.  

Itoya Department store is full of notebooks, fancy paper, beautiful pens, and well designed items for any curated home office.

Tucked away in Ginza is Cafe de l’Ambre, a well splendid but low key great cup of pour over coffee. It's like they used to do it in the old school post-war days. 

Ginza is also home to the Kabukiza Theater, worth a tour or a walk by.



Tsukiji Fish Market is fun even if you don’t get up early for the tuna auction. The area is packed with cheap and outstandingly fresh fish. I especially liked the small shrine for fisherman nearby. too. 

Vending Machines. Everywhere.

Explore Ueno Park then stroll into older Tokyo by going to Yanaka Ginza. The later is the only area of the city spared from the bombings of World War Two. 

Go to the top of Roppongi Hills complex for the Mori Art Museum’s contemporary collections and panorama of the city.

Learn about Edo Japan at the Edo Museum. I especially liked all the detailed models, being a tiny things lover. 

Walk along the Sumida river to just get lost.

Tips and Observations

Take note of what exit you need in a train station as most of them are so large, it can be a pain if you exit too early and have to walk around an entire block or more.

Every station will have an attendant to help you. Hooray!

Every train station will have a bathroom, too. They will be clean but often feature western and squat toilets, so do take note! There is also a lack of soap frequently in bathrooms. This confused me a lot for a country that is so organized and clean. It's better to bring hand sanitizer.

People don't talk on trains but as a tourist I think its okay if you are chatting quietly. It's an orderly process of travel, though. I'm talking people line up to get on a subway, with no touching, shoving, or any kind of rude behavior most of the time. It was fantastic!

English is everywhere but it's illustrative, meaning people think English is cool on t-shirts, signs, etc the same way we kind of use French sayings on things to make it seem cool. So people were helpful but are definitely not fluent in English conversationally everywhere you go. It helped to do some research before hand on what sorts of Japanese sayings you'll encounter when you enter a store, etc.


To say that I experienced culture shock when in Japan seems like a cliche. But it's true, especially for me.

The strongest feeling I had while in Tokyo was that it's cosmopolitanism is at once familiar and yet strange, like waking up at night with the lights on. Just like you're at first confused where you are, unsure if you're still in your room.

I took to making notes every time I encountered something I didn't understand which ended up with an entire list of things I want to know more about in Japanese society

Why do the trains play jingles at the station?  Why do people not talk on crowded trains, or hold hands? Why are smart phones and flip phones popular in Japan? How do they run a city so efficiently, with such density, with what seems like a chaotic mix of lights, buildings, and competing private companies? What is Japanese class, poverty, and race like compared to the USA because despite there being no crime and almost no trash, there are stratifications below the surface. How and why do they read books and buy cds (!!) in droves? Why do they just love those darn paper calendars?

It's hard to understand another culture in a glimpse of course, so Tokyo provoked a lot of interesting questions that I'm still sorting through. For that, I'm glad I made the trip and I hope to make it back to just keep figuring it out.

But man, do I feel like I finally understand Kinokuniya bookstore in New York City though. I