Tokyo: the city that changed how I travel
How my honeymoon went off-script in Tokyo, plus my full city guide with where to stay, eat, and shop
This is From the Window Seat, a series of deeply researched, design-forward dispatches for people who believe in the art of traveling well. From immersive itineraries to standout hotel reviews, each one offers everything you need to experience a place—or a property—with intention and great taste.
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We were supposed to go to Osaka, but just a few days into our stay in Tokyo, we decided to cancel all of our plans. Let me explain.
In the fall of 2023, I was gearing up for what was set to be my most exciting trip yet: not just my honeymoon, but my first-ever journey to the other side of the world. My husband and I planned to celebrate our marriage by spending ten days in Japan, and the planning of this trip was my pièce de résistance. The itinerary was locked: Tokyo, Osaka, and Kyoto. Trains booked, bags packed, and the itinerary color-coded within an inch of its life. With so much to do and see, I didn’t want to leave anything to chance.
But three days into Tokyo, something shifted.
The itinerary (our bible) told us to hop on a train and head to Osaka, where we would keep the trip moving, and see as much as humanly possible. But there was this shared moment in the back of a cab—my husband and I both looking out our own window at a city we weren’t ready to leave—when we turned to each other with the same knowing glance. We confirmed our thoughts were the same:
What if we just stayed?
Seems like it should have been simple enough, right? But it was logistically messy (rebooking a bullet train in Tokyo Station is no joke) and, more surprisingly, emotionally complicated. I had to give myself permission to loosen my grip on the plan I’d set so firmly in place. To release the itinerary I’d memorized in favor of what had yet to be discovered. To let go of the comfort of knowing what came next, and find peace with not knowing at all.
So, that’s what I set out to do.
We scratched Osaka off my carefully constructed itinerary. Rebooked our hotels. And gave ourselves a gift I never would’ve considered before: more time in one place. We wandered. We got lost. We found the best izakaya while ducking into shelter from the rain. We stayed in a hotel that redefined luxury for me. It ended up that my favorite moments weren’t on any itinerary, and I want more trips like that.
So you can see, this trip was special for more reasons than just the occasion or the destinations. It showed me the magic that can happen when you stop rushing between them.
Below, you’ll find a tightly curated edit of my Tokyo picks: what I loved this time around, plus the spots at the top of my list for next time. From design-forward hotels and neighborhood cafés to thrift stores, listening bars, and places that didn’t make the itinerary, I’ve gathered everything worth bookmarking.
Read on for:
The Tokyo stays with the best skyline views and Japanese breakfast
My go-to shops for design, fashion, and vintage finds
Where to eat (and drink) like a local, rain or shine
The shoes I actually wore for 20k step days (and the ones I wish I packed)
I went in early October, and while the temps oscillated between 60 and 80 degrees Fahrenheit, it still felt surprisingly hot for the time of year. One day I’d wear jeans and a cardigan, the next a tank top and a sporty skort. The only constant? Sneakers. Non-negotiable. No matter the outfit or the forecast, you’ll be walking 2–3x more than you expect, trust me.
But I get it. Personally, I’m not someone that a Sneaker Look™ comes effortlessly to, so here are my recommendations for footwear:
You do have to pack some kind of sturdy sneaker, no matter what. Just find which one works best for you. For me, it was these chromed-out Nikes. Next time, I’d opt for these Asics. For you, it might be Salomons.
Bring a low-profile sneaker. This sleaker option lends itself to different styling opportunities. For example, Nike Cortez’s have a solid amount of cushion that make them great for walking.
And finally, flats. Rothy’s are going to be the comfiest option IMO; these are my pick. I haven’t tried these, but people say Margaux or Sam Edelman are also great for going the distance.
Oh, and in case you are an American Dyson Airwrap owner: they work in Japan without a transformer!
Where I stayed this time
Conrad Tokyo: A Skyscraper hotel with sweeping views of Tokyo Bay located in Shiodome. I didn’t love the business park location, but it was conveniently located right across the street from Hama-rikyu Gardens and within walking distance of Tsukiji Market. Very nice hotel with spacious bedrooms and bathrooms, and the best Japanese breakfast of the trip.
Park Hyatt Tokyo: Shinjuku hotel known from Lost in Translation with panoramic skyline views and the iconic New York Grill. We booked this the day before arriving, so they were out of King bedrooms, so they pushed two full-sized beds together to make a one giant mega bed for us. We also arrived to flowers, champagne chilling on ice, and chocolate. The level of hospitality here actually blew me away.