Sunset from the Metropolitan Government Building in Shinjuku.

It’s said that if you’re drawn to a particular city, it means someone is there waiting for you, or there’s a part of your story already written, awaiting your discovery. If that's true, the person waiting for me in Tokyo is my higher self, and what’s written is the chapter where I’m disgustingly wealthy, romping around Harajuku like a matcha-fueled sprite.

The fascination with Japan, particularly Tokyo, has been lifelong. But over the past decade it’s become a palpable, all encompassing, overwhelming destination of desire, that the phrase “wanderlust” would not suffice to describe.

Having travelled to Japan twice in the past six months is nothing short of a fever dream. The residue of Shibuya’s dystopian neon glimmer leaving a heartsick Lost in Translation yearning in every part of my Sofia Coppola-Girl being. Recently released from the shackles of suburbanite Stockholm syndrome, my small-town self still cannot believe I now live in a walkable city thanks to the Japan effect.

This past spring, my husband, mother-in-law, four children, and I took a two week vacation in Tokyo, Kyoto, and Osaka. The proverbial International Family Vacation is not for the faint of heart as we found out, but the testing of our mental and physical fortitude was rewarded with a memorable trip and enough newfound wisdom to avoid many (unfortunate) things that made it memorable in the first place.

The most recent stay, at the end of October, was a no-frills weeklong work conference trip for my husband while the oldest three kids (ages 14, 13, and 10) stayed back to enjoy an empty apartment, stocked pantry, no school, and family members nearby for entertainment and company. Bliss for everyone involved.

And it’s safe to say, that every feeling-of-belonging was amplified this second time around, feelings first realized in the spring, sitting on a park bench with my husband on the last day of our trip. That initial conversation led to a steady back-and-forth, resulting in our summer move from Maui to O‘ahu (a mere month later), with the goal of being one step closer to a life lived part-time in Japan (and to simply enjoy being out of Maui, a story for another time).

All that aside, this post is a means to share a few favorites and insights from our time and travels there so far. It’ll focus solely on Tokyo, with a write-up on Kyoto and Osaka sometime in the future. The hope is to build upon this into a series as I evolve into a seasoned Japan regular, God willing (are you there, God? It’s me, Chanelle).

Now truth be told, I am a travel princess, meaning my husband so kindly in all his organized vigor and strategizing intellect handles everything from booking flights to arranging accommodations, from mapping our train route to scheduling our daily itinerary based off of how much matcha I need to consume and how many bookstores I need to browse in, naturally. I don’t lift a finger, except to pregame the trip by drowning in Japan vlogs, bookmarking every potential destination in Google Maps, and just being my fabulous manic self. So I am not at all the person to ask about such things, however I do know there is a plethora of resources online. Not only that, but do yourself a favor and use your dopamine-fueled social media addiction to train the algorithm into ferrying relevant travel content your way. There is no shortage of creators with content tailored for this exact purpose, so you might as well milk it for what it’s worth.

Some favorite resources

After a year of vlog binging, our favorites are Ralph & Sam. I don’t think you’ll find a traveling, vlogging couple more down to earth, without the grating influencer-speak or proclivities that plague the internet.

YouTube is also your friend when learning a handful of phrases (and their pronunciation) to get you through the trip. Having a few of these in your pocket, as well as having yen on you at all times (don’t depend on solely using a credit card) is key.

Get yourself familiar with the train system in general. Here’s a helpful video.

This When In Tokyo website is a gem.

Go Tokyo, the official Tokyo travel guide.

Some helpful tips

You need the internet and a usable phone! Opt for an eSim or portable wifi.

Prepare to easily rack up 10k-20k steps daily, so pack your best shoes.

Bring your passport with you while shopping! Many places offer tourists tax free prices if you have your passport for proof.

Download a Japanese taxi app (like this one). In a pinch if your budget is flexible, you may want to opt for a quick taxi ride rather than take the train, especially after your arrival flight. From experience traveling with kids or small babies, a taxi ride can be worth the extra money, don’t let anyone convince you otherwise.

If you’re city-hopping, opt for a luggage forwarding service that is often offered by hotels, and can be found in certain train stations (I believe). Navigating from city to city is far easier without the (literal) baggage, especially when commuting by train.

From priority sections on train cars, to special elevators, Japan is very considerate of the elderly, disabled, pregnant women, and women with young babies and children. If you’re out and about and need to nurse, change a diaper, or simply need a break from walking and strolling, there’s no shortage of clean and spacious feeding and changing areas in train stations or elsewhere. A trick is to find the nearest department store and chances are you’ll find one. The high-end department store Isetan is amazing, with an entire floor dedicated to designer children’s clothing, equipped with an art gallery to dress the walls of your posh baby nursery, and a cafe with bed-couch seating for optimal mommy-and-me lounging. America could never.

My sweet husband (and the backs of two of our children) on the train to the Osaka aquarium.

TOKYO

The view from the Metropolitan Government Building in Shinjuku; Spring 2024

SHIBUYA

Out of all the places we’ve visited within the city, Shibuya is by far one of my favorites, perhaps influenced by our second stay exclusively in the area. It’s vivid and lively, dense and electric, like the buzzing central heartbeat of a circuit board. Oftentimes crowded, with claustrophobic hoards shuffling through Shibuya Scramble Crossing or scuttling in and out of Shibuya Station, its chaos (that divides many an opinion) shouldn’t deter you from exploring its offerings.

In October we stayed right in central Shibuya, the Scramble Crossing seen right from our hotel. Our trip spanned the week of Halloween, so we anticipated seeing some characterful shenanigans. However, a recent law has been permanently passed banning public drinking in certain areas at certain times of day, especially on Halloween and New Year’s Eve. So instead we encountered heavy police presence securing the area (with buses awaiting the detention of any miscreants), herding crowds across the famous Scramble crosswalks like cattle in an orderly, un-scrambled fashion. Quite a sight to behold.

Shibuya favorites

Miyashita Park is a hip little shopping mall with lots of food options, coffee shops, and an outdoor park area on the top floor with seating, nice views, a skate park, and even a rock climbing wall. One of my favorite burgers is here, as well as my favorite matcha spot. Also inside: Face Records and High Tide Store.

Shibuya Tokyu Food Show - This two floor food hall was underneath our hotel!

LOFT - One of my favorite stationery spots on the bottom level (which also connects to a MUJI), with other floors dedicated to home goods, gifts, and the like.

Shibuya Publishing & Booksellers

JAM Vintage - Vintage leather jackets galore.

Tower Records

Disk Union - A rare jazz cd & record shop

Manhattan Records

DAIKANYAMA

One of the more beautiful districts in Shibuya is Daikanyama, a high-end partial residential area with a Brooklyn-esque vibe. We came here with a particular destination in mind: Tsutaya Books, a dual building, multi-storied bookstore. Both this location and its Ginza location (that we visited in the spring) are the most beautiful bookstores I’ve ever been in.

Nestled next to Tsutaya is one of two Princi Tokyo locations, a small Italian bakery and cafe adorned with large window seating amidst the cozy atmosphere. We stopped there first for some sweet treats that were chef’s kiss impeccable. Sterling and I stopped drinking coffee earlier this year, but I should’ve opted for something here instead of the Starbucks within the Tsutaya (what a wasted experience, however, coffee and matcha are still really good in Japanese Starbucks’!).

OMOTESANDO & HARAJUKU

Omotesando and Harajuku bleed into one another. Omotesando is an area known for luxury shopping, architectural eye candy, and classy little cafes. Harajuku, namely the back streets of Ura-Hara, cater to the younger hip crowd.

A handful of favorites

GYRE is a shopping building with both retail shops and restaurants. On the 3rd floor is a MoMA Design Store, and on the 4th floor a gorgeous eatery called uni that you won’t want to miss, even for a photo op. On the bottom floor is HAY Tokyo and Cibonne both with a beautiful and fun curated selection of furniture, interior design goods, and the like. KINJI in Harajuku is a thrifting must.

SHIMOKITAZAWA

If you’re looking to thrift (you’re going to Japan, of course you are), Shimokitazawa is ideal (this Reel shows you the vibe). Prepare enough time for your visit here (a quick train ride from the heart of Shibuya) to dig through the overwhelming amount of shops you’ll stumble upon. Even while operating from a “scan everything quickly” mentality rather than a slow and careful thrift gaze, we spent almost 5 hours wandering around.

From what I’ve gathered, a large portion of thrift and secondhand shops will have no shortage of men’s workwear and outerwear (Barbour, Carhartt), vintage leather jackets (I snagged one myself), denim, and lots of Champion, Ralph Lauren, Tommy Hilfiger, and funnily enough: Hard Rock Cafe graphic tees.

THRIFTING

KINJI - Kinji’s have a bit more variety than some of the other thrift shops. You’ll also find some smaller racks with vintage designer pieces. I regret not buying a weird oversized corduroy coat from this location. Le sigh.

ANCHOR

DYLAN’S - Definitely loved the atmosphere here, and regret not buying a vintage pair of Marlboro jeans.

TREFACSTYLE (Location 1) - Larger location of the two with a nice variety. This is where I bought my leather jacket and brown coat.

TREFACSTYLE (Location 2, East Exit)

Stickout - Lots of sweaters and denim.

Ruby’s

Toyo Department Store - A tight space that’s more of an indoor market maze with 20+ small vendors within. Can be a bit of a squeeze especially if a lot of people are there, but you might be able to find some neat things.

GINZA

I wish we had more time to explore Ginza, one of city’s nicest shopping areas. We came here briefly during the spring, with personal highlights being the Tsutaya Bookstore in Ginza Six and Itoya, a multilevel art supply and stationery store with a beautiful (and more pricey) selection of writing supplies and desk/office objects.

If you love MUJI, this location has all the usual goodness, with an added bookshop and cafe on the top level (with delicious matcha ice cream).

If you can’t make it to the LOFT in Shibuya, there’s one in Ginza (again, for my fellow stationery and home goods lovers).

SHINJUKU

One of the most famous areas of Tokyo, Shinjuku has something going on at every hour. I’d suggest reading this to get a feel of the area (and some great recommendations), especially noting what to expect once the sun sets and crowds emerge, attracted to the bright glowing nightlife like moths to a flame. The vibe is very similar to Shibuya, perhaps scaled up to the nth degree.

A handful of recs

The Tokyo Metropolitan Government Building - If you want a stunning panoramic view of the city, you can visit the 45th floor’s Observation deck. I believe they also have a light show during certain hours of the night.

Sekaido - A glorious multi-storied art, stationery, and office supply shop with a huge variety. My favorite stop for buying painting supplies, stickers, miscellaneous supplies, and greeting cards.

Isetan Food Hall - In the basement level of this luxury department store (the one with the mommy cafe mentioned earlier), there’s a huge food hall. From fresh seafood and sushi, to ready-to-eat bento boxes perfect for lunch, you’ll be able to grab a bite and maybe some treats to gift loved ones. One of our favorite stops (still thinking about the dumplings and tuna roll).

ITOYA (a smaller version of the Ginza location)

Tokyu Kabukicho Tower - Retail and eateries

Books Kinokuniya - A local bookstore

JIMBOCHO

For the literary lovers, Book Town, as this quaint little place is coined, is a collection of streets lined with shops bursting with antique and modern books, vintage magazines, and assorted curio. I could spend an entire day here, the hours slowly dripping by as the smell of old paper perfumes my hair. If you have the chance, don’t skip strolling in the area to hunt for treasures and souvenirs.

I had bookmarked a few shops, but they seem to have escaped my Google Maps archive. However, you’ll easily find something by simply arriving and letting the pathways lure you to hidden gems.

If you’re into stationery and art supplies like I am, you won’t want to miss a trip into Bumpodo, one of Japan’s oldest art supply stores (and a cat themed one at that!)

HONORABLE MENTIONS

I’ll quickly add Nippori Fabric Town if you enjoy sewing. We went here for my daughter and there’s an overwhelming amount of fabric stores and specialty shops with buttons and other sewing goods. Our favorite shop was Tomato, although there are (I believe) 3 Tomato shops on the street!

And lastly, Asakusa is the area we stayed in during our first trip. It’s a nice area with a lot of tourist attractions, shopping, and eating.

Nakamise-Dori street leading to Senso-ji Temple, Asakusa

UNTIL NEXT TIME

Far from extensive, this list will hopefully give some of you ideas and recommendations when planning a trip to Tokyo. There truly is too much to explore with so little time, that the only way to see and experience everything is to go back often or finger’s crossed to move there. We are already scheming up a trip (or two!) for next year, so perhaps this series will continue sooner rather than later. Feel free to share this with friends and family who might get something useful out of it. Until next time, xx.

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The Tokyo Edit