The Ultimate Japan Travel Itinerary: Tokyo & Kyoto in 9 Days

It started innocently enough: a YouTube video here, a TikTok there, an opening of my Notes app to scrawl down a recommendation from a friend’s chiropractor. But soon, I was spending hours scouring the internet for “hidden gems in Nakameguro” and dropping pins on Google Maps like I was John Nash in A Beautiful Mind. What began as planning a trip to Japan eventually turned into a project, then a job, then an obsession. And honestly, I loved every second of it. 

There’s a certain thrill I get in planning vacations—choosing my adventures, imagining how they’ll play out, and convincing myself that, somehow, I’ll be able to fit it all in. I’m always a little embarrassed when people bring up my travel blog or mention that they saw photos from my recent trip on Instagram. I’ll wave it off like it’s just a silly little hobby. But deep down, I know the truth: next to performing, there is nothing I love more than crafting an amazing trip. And in the spirit of a New Year, when I’m making an effort to actually own my accomplishments, I’ll just say it—I’m really fucking good at it.

And now, here you are—maybe fueled by wanderlust, maybe Googling “how to plan the perfect trip to Japan” at 2 a.m. Either way, welcome. I poured a year of obsessive planning into this itinerary, and now I’m sharing it with you.

Six Months Out

It’s time to book your flight. Yes, six months sounds insane. But trust me, flying to Japan is a long trip, and you’re going to want to do it lying down. Business class tickets to Japan can cost upwards of $10,000, but fortunately, I’m married to someone who obsesses over tracking rewards flights as much as I obsess over dinner reservations. In June, he found us two first-class tickets on the ANA Suite—essentially a private, mini hotel room in the sky, complete with a closing door, gourmet dining, and pajamas—all paid entirely with Amex points. We pulled the trigger without a second thought.

Start making reservations. Japan has more Michelin-starred restaurants than any other country, with over 400 scattered across the country, many of which won’t break the bank. However, getting seats at some of them is cutthroat. Book experiences now—if you want to visit Tokyo's tallest observation decks, drive a MarioKart around Shibuya, get TeamLab tickets at a desirable time, or experience a traditional tea service in Kyoto, do it now. You’d be surprised how quickly these things sell out. Most are refundable up to a week before, so there’s no real risk.

If you’re traveling within Japan, chances are you’ll take the bullet train, or Shinkansen. It’s an incredibly fast and comfortable way to get around. If you're going during peak season or carrying oversized luggage, book your tickets as soon as they’re released (typically a month out). Some of the best restaurants also only open reservations a month in advance. I had our hotel call the moment a few of my top picks went live, and I still couldn’t secure some—so always have a few backups ready. Fortunately, Japan has an absurd number of phenomenal restaurants, so even a last-minute option will likely be excellent.

Now’s also a good time to book your airport transfer. We splurged on taxis to and from the airport. We had originally planned to take the Narita Express on the way back, but by the end of the trip, the thought of lugging our suitcases up and down train station escalators felt brutal. We canceled the train and booked another cab. I recommend Klook—you can choose your car size, and the driver will contact you via WhatsApp in translated English, making pickup seamless. It also beats waiting in a taxi line after a long-haul flight.

One Week Out

Fill out your immigration forms in advance to avoid the slow-moving arrival line. You can do this online [here].

Download a Suica card to your Apple Wallet and preload it with at least ¥20,000. It’ll be your best friend for tapping in and out of subways, convenience stores, and vending machines. Here’s a [step-by-step guide] on how to set it up.

If you need WiFi—and trust me, you will—international data can get expensive, and you’ll absolutely be relying on Google Maps. If your phone is unlocked, I recommend using an eSIM. I’ve used Airalo before; setup is a little finicky, but it works great. Since my iPhone is locked to AT&T, I went with a pocket WiFi instead. It meant carrying around a small router and charging it each night, but NinjaWiFi was fast, easy to use, and saved us over $100 in data charges. You can pick it up and drop it off easily at Haneda or Narita airports.

Three Days Before

Time to pack! If I’m being honest, I usually start a week out, but I don’t expect everyone to share my level of travel prep OCD. You’ll probably have last-minute shopping you’ll need to do — things like power adapters (Japan uses the same voltage as the U.S. but only has two-prong outlets, so you’ll need a converter if you’re bringing a laptop).

Japan: The Itinerary

So you’ve arrived in Japan. Congrats! You now get to seamlessly enjoy your months of planning! Here is my painstakingly researched itinerary for nine days in Japan. Feel free to steal as much as you’d like. 

Day 1 (New York) 

We flew United Business to Tokyo—my go-to airline thanks to its extensive domestic routes and how easy it is to build status. We used United points to book two business class tickets for the trip. While United’s business class isn’t over-the-top luxurious, it’s a solid, reliable product: comfortable seats, decent food, and consistently dependable service.

Day 2 (Tokyo: Ginza, Shinjuku)

We arrived at Haneda Airport, which is the closer of Tokyo’s two main airports to the city’s central tourist areas. After breezing through immigration—thanks to filling everything out online and simply scanning our barcodes—we picked up our pocket WiFi from NinjaWiFi. We had also pre-arranged a taxi to our hotel via Klook. There are plenty of ways to get into the city from Haneda, including trains and the limousine bus, but we opted to splurge a little in order to maximize our time exploring on that first day. The hotel transfer cost $66 USD, and the driver contacted us in advance via WhatsApp with pickup instructions.

Our biggest splurge of the trip was three nights at Aman Tokyo. It had everything you’d expect from the Aman brand. Every detail was considered—from the attentive, but never overbearing staff, to the dramatic architecture of the sky lobby, to the daily gifts (our favorite was a box of perfect berries).

Our room was a minimalist dream, blending traditional Japanese elements like washi paper and wood paneling with modern comforts. The view of the Imperial Gardens would have made waking up easy, even if we weren’t completely jet-lagged.

Breakfast became a daily highlight, whether in the restaurant or delivered to our room. The hardest decision was choosing between the Western spread or the meticulously arranged Japanese breakfast that felt almost too beautiful to eat.

One thing I couldn’t capture (thanks to a much-needed “no photo” policy) was their onsen, which featured a giant heated bath with floor-to-ceiling views of the Tokyo skyline. I used it every morning, soaking in the warmth while watching the city come to life below—a moment of calm before diving back into the chaos of exploring Tokyo.

Would I have liked to save a few more yen for gifts and clothes? Absolutely. But would I book it again? Without question.

We dropped our bags and headed straight for the neon lights of Shinjuku, a steampunk sci-fi fever dream come to life. After checking out the Cat Board—a massive curved digital screen above Shinjuku Station where a surprisingly realistic 3D calico cat stretches, yawns, and occasionally bats at the ads—we ventured over to Omoide Yokocho, AKA Piss Alley, a narrow maze of smoky grills and tiny bars. We stopped and grabbed a yakitori dinner at Banshaku-ya, a comparatively large restaurant for Omoide Yokocho, but still tiny by any other standards. I managed to mutter my basic restaurant Japanese (which would get progressively better over the course of the trip) to order and pay the check, but the waitstaff all seemed to speak English. The food was delicious and a good, authentic first bite of Japanese cuisine—a harbinger of incredible meals to come.

Next, we explored Kabukicho, Tokyo’s infamous red-light district and entertainment zone, where love hotels, robot shows, host clubs, and themed cafes all exist side by side. We passed the giant Godzilla peering through buildings and the raunchy and electric billboards. We broke a sweat at the arcades in Kabukicho Tower—we especially loved Taiko no Tatsujin, or more colloquially, “the drum game,” which is way harder than it looks.

We ended the night by weaving our way through the divey, quirky bars of Golden Gai, a pocket-sized nightlife district where over 200 tiny bars are crammed into a few narrow alleyways, each with its own vibe, theme, and loyal regulars. (Suggested bars: The Open Book, Albatross, Balloon Bar.)

We ended the night back at the Aman with the Tokyo skyline glowing in the distance, feeling jet-lagged but utterly alive.

Day 3 (Tokyo: Tsukiji, Harajuku, Shibuya)

The good thing about jet lag is it means you’ll be the first tourists to arrive at Tsukiji Market, a sprawling hub of seafood vendors and street food stalls that’s been the heart of Tokyo’s food scene for decades. Touristy? Yes. Missable? Absolutely not. Our first bite was A5 Wagyu topped with sea urchin at Tsukiji Ihachi, followed by a six-piece set of the fattiest, most melt-in-your-mouth tuna I’ve ever tasted at Maguroya Kurogin. Then skewered eel at Unagi Shokudo, Mitarashi (sweet soy sauce mochi balls), a matcha latte at Matcha Stand Maruni, and candied strawberry skewers and daifuku at Solatsuki were next, each bite somehow better than the last.

Fueled by the feast, we hopped on Tokyo’s impeccably clean and impossibly efficient subway to Harajuku and its famous Takeshita Street. Once a hub for avant-garde fashion and youth rebellion, it’s evolved into a bit of a tourist trap overflowing with colorful shops, pig cafes, and girls dressed as anime characters—definitely worth a peek, but certainly overwhelming. A short walk through the peaceful park surrounding Togo Shrine led us to Anakuma Cafe, a stall with a single ordering screen and a hole in the wall where a disembodied bear claw reaches through to play games with you before serving up coffee drinks. It perfectly embodied Japan’s playful spirit, where even as an adult, you’re invited to delight in the whimsy of it all.

After some serious damage at Harajuku’s impeccable designer thrift shops (highly recommend the Kindal chain of vintage stores), we made our way to Shibuya Crossing, where hundreds of people flow through the intersection in perfect, chaotic harmony. It’s the kind of place that makes you stop and think, yep, this is the Tokyo I imagined.

With Japan boasting more Michelin-starred restaurants than any other country in the world, it felt insane not to try at least one. We chose DenKushiFulori, an inventive collaboration between the Japanese restaurant Den and French restaurant Florilège—both consistently ranked among the world’s best. The meal was playful, imaginative, and (miraculously) didn’t completely bankrupt us.

Day 4 (Tokyo: Daikanyama, Nakameguro, Shimokitazawa, Kayabacho)

After two whirlwind days, our third day in Japan was a chance to catch our breath and explore Tokyo’s coolest corners at a more relaxed pace. We spent the morning exploring the neighborhoods of Nakameguro and Daikanyama, often called the Brooklyn of Tokyo. We started at the Kyu Asakura House, a beautifully preserved Taisho-era home with intricate wooden architecture and gardens still bursting with autumn colors. Next, we strolled through Nakameguro’s stylish streets, popping into shops (recommend Visvim General Store, Overchord, Traveler’s Factory, 1LDK), and eventually landing at Onibus Coffee, an incredibly vibe-y place to sip third-wave lattes while watching the trains pass by.

Two silly bucket list items were trying the occasionally deadly pufferfish, or “fugu,” and grabbing a meal at a conveyor belt sushi joint. We managed both at Kura Sushi. Sure, it didn’t hold a candle to the sushi we had the day before, but the novelty of snatching plates off the belt was ridiculously fun.

In the afternoon, we headed to Shimokitazawa, a hipster haven and absolute thrifting paradise. I’ve never seen such a density of high-quality vintage stores, and unlike the chaotic racks you’d find in the States, everything here was impeccably organized, color-coded, and pristinely clean. I particularly loved Flamingo, DESERTSNOW, WEGO and 2nd Street.

The perfect antidote to the Tokyo's nonstop sensory overload was sitting in almost complete silence while one of Tokyo’s few female sushi chefs worked her magic at Sushi Uraonikai. An omakase sushi experience is a must in Tokyo as it introduces you to bites and cuts of fish that you may not necessarily gravitate to on your own. Each bite was a testament to her artistry, crafted with precision and care.

Day 5 (Tokyo to Kyoto: Higashiyama, Gion) 

If you’re visiting Japan for the first time, you’ll likely want to expand your trip beyond just Tokyo, and to do that, there is no easier or more relaxing mode of transportation than the bullet train, or “Shinkansen.” This train is proof that Japan really is out here living in 2050. At speeds topping 175 mph, it makes the 2-hour ride to Kyoto fly by. If you plan on traveling with multiple suitcases, I really recommend booking the green car which is their version of business class. There’s a bit more leg room and if you book the front or last row of seats, you have an oversized baggage area. There are many ways to book tickets on the Shinkansen, but I recommend doing so on the SmartEX website where you can choose your seats. Make sure you book the D/E seats in ordinary cars or C/D in the green cars for a view of Mt. Fuji out your window. Tokyo station itself is a bit overwhelming, so arrive at least an hour ahead of time to get lost and find your gate. You’re also going to want to buy bentos or “ekiben” at Ekibenya Matsuri Gransta to eat on the train. I recommend trying the self-steaming bentos which warm themselves buy pulling on a string. The one I got was packed with real crab and Wagyu and tasted as good as any food you could find on an airplane.

Probably my biggest slay of the trip was finding our lodging in Kyoto. After hours of scouring hotel booking sites and finding only outrageously expensive luxury hotels or moderately priced ones in inconvenient locations, I turned to Instagram and started scrolling through location tags. What I found looked too good to be true: a vacation rental steps from the Yasaka Pagoda.

The hotel site wasn’t in English, and I fully expected to walk in and discover I’d made some grave mistake or that the photos had been a total scam. Instead, we were met with a stunning two-story machiya (traditional wooden townhouse) complete with a kitchen, two baths, a cozy sleeping area, and a separate tatami room with an iconic view of the Yasaka Pagoda. Our front door literally opened up to the most photographed street in all of Kyoto. I almost hate to un-gatekeep this spot since it’ll probably be impossible to book again—but you’re welcome, friends. The name of this incredible vacation stay is the Campton Kiyomizu.

Just around the corner from the Campton is K36, a rooftop bar with stunning views of the Kyoto skyline—perfect for sipping cocktails as the sun sets over the city.

Higashiyama, the area where we were staying, felt like stepping onto the set of Shōgun with its narrow streets lined with wooden storefronts and temples. It was also within walking distance of Gion, Kyoto’s historic geisha district, where we had kaiseki dinner at Gion Mametora. Set inside an old tea house, we were served the meal in a private room. Each dish was absurdly photographable and felt almost too beautiful to eat—almost.

Day 6 (Kyoto: Arashiyama, Pontocho Alley)

For our second day in Kyoto, we had grand plans to wake up at the a$$crack and head to the Bamboo Forest in Arashiyama. You know the place. It’s the one everyone, without fail, posts a photo of when they visit Kyoto. I knew if we waited until even 10 AM, it would already be too late; the peaceful forest would turn into a full on cattle chute of tourists. Think the Highline of NYC. But at 5:30 AM, as I reached over to silence my alarm, Scott whispered the six most beautiful words in the English language: “What if we just slept in?”

By the time we woke up at 9 AM, we still decided to train it over to Arashiyama, a picturesque district nestled in the mountains. I wasn’t about to miss our lunch reservation—one I’d made months in advance—and thank goodness because it ended up being our favorite meal, if not our favorite experience, of the entire trip.

Arashiyama Itsukichaya is a riverside restaurant I’d seen on TikTok, which can be hit or miss when it comes to recommendations, but as soon as we were seated, I felt full-body, hair-on-the-back-of-your-neck chills. We were overlooking a river and a gentle waterfall surrounded by Japanese maples glowing red, with ducks gliding peacefully below. At that moment, the food didn’t even matter; we were already so blissed out that I would have been happy just watching the ducks. It was like ASMR for your eyes

But oh the food! It somehow managed to top the view. The meal featured seven perfect dishes, each requiring a bit of assembly — breaking a yolk over golden rice, pouring dashi over fresh sashimi, or boiling tender meat and vegetables in a bubbling miso broth. It was interactive, satisfying, and utterly delicious. Scott said it felt gratifying in the way that building Legos feels gratifying and honestly, I understood him completely. If you do one thing in Kyoto, let it be this. They book two months out, and river-view seats go FAST, so set a calendar reminder.

After lunch, we decided to try our luck at the Bamboo Forest. If it was too crowded, we’d skip it. But just as we reached the crowded main street, our luck turned — a light rain started to fall, the kind I personally don’t even need an umbrella for. Within minutes, the tourists scattered into shops, leaving the path nearly empty. By the time we arrived at the forest, it was shockingly quiet, and the towering bamboo provided natural cover from the drizzle. The sound of the wind gently knocking the bamboo together was unexpectedly soothing—one of those magical, unplanned moments that feel too good to be true.

As we exited the forest, the sun broke clouds, casting everything in a golden glow so we decided to keep wandering up to Saga Torimoto, a preserved historic street lined with traditional wooden houses and grand estates. It was so tranquil, we barely passed more than a handful of people the entire time—just a few locals and the occasional tourist quietly taking it all in.

You also pass a number of beautiful temples along the way, including Jojakkoji Temple, Gioji Temple, and Adashino Nenbutsuji Temple.

On our way back to Kyoto, as we crossed the Kamo River, we were greeted by a massive rainbow arching across the sky. It felt like one of those movie-perfect travel moments—the kind that makes you fall even harder for a place you’re already obsessed with.

I turned to the TikTok girlies once again for our dinner pick and landed on the wildly popular Gyukatsu Motomura, a steak cutlet spot with locations all over Japan. You grill your own breaded wagyu on a hot stone and pair it with an array of dipping sauces. The lines can be intense, but a few branches in Kyoto take reservations—including the Sanjo Kawaramachi location, which comes with bonus views of the Kamo River. The meal is surprisingly affordable, and while it sounds like a cliché, the steak really does melt in your mouth.

Day 7 (Kyoto: Kiyomizu, Shimogyo, Downtown Kyoto)

On our final full day in Kyoto, we managed to wake up super early, fueled by 7-11 coffee and their dangerously addictive pancakes (I know what you’re thinking, but convenience stores, or “konbinis” in Japan are actually god-tier). Also, while we’re on konbinis, let’s talk about one of the favorite things I brought back which came from Family Mart, a 7-11 competitor which you can find all over Japan. Aside from tasty snacks, they also sell literal clothing including plain white tees that are of shockingly good quality and are cropped to the perfect length. I bought one, tried it on and then returned the next day to buy three more and they are now my go-to plain tees.

Our morning began with a quiet, almost meditative walk through our beautiful neighborhood of Higashiyama, enjoying the peace before the throngs of tourists arrived. The first thing on our agenda was visiting one of Japan’s most iconic landmarks, Kiyomizudera Temple. 

Full disclosure: we’re not temple or cathedral guys. I feel like I learn a lot more about a country by spending an hour at a restaurant than any church or shrine, so when I was planning, the temple felt more like something we had to check off our list, something we couldn’t *not* do. But I am SO glad we did as it ended up being one of favorite places we visited.

Arriving just as the sun was rising, we practically had the temple to ourselves. Pictures truly don’t do it justice—the sheer scale and the way its massive wooden stage juts out over the hillside is something you have to see to believe.

Next, we wandered over to Shimogyo Ward and refueled at Walden Woods Kyoto, a minimalist dream of a coffee shop with whitewashed walls and ginger lattes as good as the aesthetic.

One of the things I was most excited to do in Kyoto was visit Nishiki Market, often referred to as "Kyoto's Kitchen.” It is over 400 year old and packed with vendors hawking fresh seafood, local produce and street food. Our favorite bites? Tempura shrimp with matcha salt, cheesy takoyaki, tender chicken skewers glazed with sweet soy sauce, and taiyaki filled with red bean paste and dripping with butter. And let’s not forget the 100-yen (64 cents!) glasses of sake, which somehow tasted even better standing shoulder to shoulder with strangers.

The afternoon was all about tradition. We attended a the Ju-An tea ceremony at Ju-An at Jotoku-ji Temple. While we learned the deliberate, graceful process of preparing matcha.

While I’d taken the lead on most of the trip planning, Scott had one special request: to find a piece of kintsugi, the Japanese art of repairing broken pottery with gold, to bring back home. I upped the ante and booked us a private kintsugi class through Wabunka Japan. A local artisan guided us through the process, and we got to repair four pieces ourselves. It was such a rewarding experience, and now we have a piece of Kyoto’s philosophy—embracing imperfections—sitting in our apartment.

By the end of the day, we were completely exhausted but still found room for a comforting bowl of udon, one of Scott’s favorite dishes, at Omen Shijo. We didn’t have a reservation for this place, but we arrived around 5PM and had no trouble getting a seat.

Day 8 (Kyoto to Tokyo)

After a slew of early mornings, we let ourselves sleep in a bit before heading out to pick up some last-minute souvenirs and gifts for family back home. A few spots we loved: Ninen-zaka Marun for intricate sushi-shaped confections that are almost too pretty to eat, Nittodo Kyoto Café for beautifully packaged coffee beans and sleek thermoses, and 手作り箸工房 遊膳 祇園店 for hand-crafted chopsticks (just copy and paste those characters into Google Maps and you’ll find it easily).

Our final stop in Kyoto was Kōdai-ji Temple, a serene Zen temple with landscaped gardens, elegant architecture, and a peaceful bamboo grove tucked behind the main complex. It was incredibly quiet, with far fewer visitors than Kiyomizu. The bamboo forest here is much smaller than the one in Arashiyama, but the total lack of crowds meant we could get stunning photos without anyone else in the frame.

After a quick ride on the bullet train back to Tokyo, we checked into the Andaz Toranomon Hills. We were only staying for one night, but we were determined to make it count. Our main reason for booking it? The jaw-dropping views of Tokyo Tower from select rooms. Since it was Christmas Eve and we weren’t going to have a tree at home, the glowing red-and-white tower felt like the perfect urban stand-in.

One tip I picked up from the kiddies on TikTok: pack an empty suitcase inside your checked bag for all the shopping you’ll inevitably do. And wow, did that extra suitcase come in handy. Shopping in Tokyo is no joke. Between the designer thrifting, J-beauty skincare, and Christmas gifting, I had a whole list of items to bring home. After settling in, we headed to Ginza to pick up a pair of limited-edition Onitsuka Tiger sneakers for Scott’s brother, then made our way to Akihabara for souvenirs.

Akihabara is Tokyo’s electric town—an over-the-top paradise for anime lovers, gamers, and gadget geeks, lit up by giant neon billboards and packed with multi-story arcades and specialty stores. One of the main reasons we went was to visit one of the biggest Don Quijote stores in Japan. Don Quijote is a chaotic, multi-level discount emporium that sells everything from candy to cosplay, and yes—it has its own jingle that will be permanently lodged in your brain. (You’ve been warned.) Some skincare staples I now swear by came from there: Curel Moisturizing Spray, Anessa Mineral Sunscreen, DHC Lip Cream, Melano CC Vitamin C Serum, and the world’s best nail clippers. In fact, I lost mine, so if you’re going, grab me a pair—kthxbyeee.

One Japanese Christmas tradition I learned about is ordering a special KFC dinner. I know—it sounds wild—but there’s actually a fascinating backstory involving a brilliant marketing campaign that positioned Colonel Sanders as a kind of jolly Japanese Santa. We thought it’d be a fun high-low way to cap off the trip: sharing a bucket of fried chicken in our hotel room with Tokyo Tower twinkling in the distance.

I had read that you needed to reserve your KFC in advance, but the process was genuinely confusing—even for me—so we tried our luck in person. Hilariously, after a week of eating at Michelin-recommended restaurants, the only place we were flat-out refused service was a KFC. The employee kindly informed us that they were fully booked for the night. So, we went on a quest for fried chicken elsewhere and found Karaage-ya Oshu Iwai in Akihabara. It also seemed to be reservation-only, with a line of people clutching little slips of paper for pickup.

It was the one time on the trip when my basic restaurant Japanese completely failed me. I became that American tourist, awkwardly trying to explain that we didn’t have a reservation but were desperately hoping they could make an exception. Something about our tired faces, our off-the-beaten-path determination, or maybe just the Christmas Eve magic must’ve worked—because the man behind the register eventually looked at me, paused, and said: “Wait.” Minutes before closing, he handed me a heaping bag of karaage—perfectly crisp fried chicken bites, hot and golden.

We ate them on a nearby park bench, and whether it was the cold air, the long journey, the spirit of the season, or just plain hunger, it was hands-down the best fried chicken I’ve ever had. The whole thing felt like the ultimate Scott-and-Andrew-on-vacation moment—messy, spontaneous, and totally unforgettable.

Back at the Andaz, we closed out the night with cocktails at the hotel bar, where a live band accompanied an excellent jazz singer crooning holiday standards. Our room was spacious and beautifully appointed, and we left the blinds open so we could fall asleep watching Tokyo Tower glowing through the window—one last perfect view before saying goodbye.

Day 9 (Tokyo to New York)

Our last morning in Tokyo, we savored the final package of 7-11 pancakes I had secured the night before and made our way to the onsen at the Andaz. The Andaz Tokyo Toranomon Hills boasts an impressive spa and wellness area, including a sleek, modern onsen that offers a serene escape from the business-focused district outdoors. The onsen features a hot tub, a cold plunge pool, and a beautifully designed sauna. The tranquil atmosphere, combined with the soothing heat of the onsen, made for a perfect, restorative start to our final day. After checking out, we had an hour to kill before our taxi, so we walked over to nearby Tokyo Tower. The views were stunning, and the peaceful park surrounding it was filled with quiet, everyday moments—people reading on benches, a group of school kids practicing marching band formations. It felt like the perfect final snapshot of Tokyo.

Luckily, saying goodbye wasn’t too painful, because we had one last splurge waiting for us: first class on ANA—the very first reservation we’d made for this trip. The first class lounge at Narita was next-level, complete with a sushi counter and stations serving made-to-order ramen and udon. The flight itself may have been the best thirteen hours I’ve ever spent in the sky. Because the seats next to us weren’t sold, we each had two pods—one to lounge and dine in, and a separate one to sleep in. The food was incredible, and at one point we were offered a pour of 21-year-aged Hibiki whisky (which, for the record, retails for upwards of $1,200 a bottle in the States). I’m not even a whiskey drinker, and I couldn’t tell you what made it so special—but it was a fun, final taste of luxury before we returned to real life.

What no one prepares you for is the culture shock of coming home from Japan. There are no people polishing the subway banisters. Public bathrooms aren’t pristine mini-spas with musical bidets. No one whispers on public transit. So landing in a city like New York? A full system reboot.

Most trips, Scott and I have that moment—you know, the one where we look at each other and say, “What if we moved here?” But this time, to my surprise, we didn’t. And that’s not to say it wasn’t one of the best vacations I’ve ever had—it absolutely was. But Japan, for us, is a place to return to, not to relocate. I’m a little too chaotic, too loud, too New York at heart.

That said… if you think I’m not already plotting my triumphant return—to finally see that monkey park in Arashiyama, catch the Robot Show in Shinjuku, or try that new buzzy cocktail bar in Shibuya—you’d be wrong.

Goodbye, Japan. Until next time.

 Mata ne.

Cheat Sheet

Tokyo Hotels

Aman Tokyo – A serene, ultra-luxury retreat high above the city, blending minimalist design with sweeping views and impeccable service.
Andaz Tokyo Toranomon Hills – Sleek and stylish with floor-to-ceiling views of the Tokyo Tower, a standout rooftop bar, and one of the best onsens in the city.

Tokyo Restaurants

Cheap Eats
Banshaku-yu – Authentic yakitori tucked into the nostalgic alleyways of Omoide Yokocho. Smoky, lively, and very Tokyo.
Kura Sushi – A playful revolving sushi chain with locations all over the city. Not mind-blowing sushi, but super affordable and fun (plus, there’s a gacha machine when you return your plates).
Karaage-ya Oshu Iwai – Crispy, juicy fried chicken spot known for its perfectly seasoned karaage.

Bars & Cafes
Anakuma Café – Your coffee is delivered through a hole in the wall by a bear paw. Yes, really. Delightfully weird and worth the detour.
Onibus Coffee – Minimalist design, excellent third-wave coffee with exciting views of passing trains.
Rooftop Bar at Andaz Tokyo – Chic 52nd-floor bar with sweeping city views and inventive Japanese-inspired cocktails.
The Tavern – Grill & Lounge (Andaz Tokyo) – Modern Japanese grill serving beautifully plated dishes with seasonal ingredients and unbeatable views of the Tokyo skyline.

Fancy Meals
Denkushiflori – A Michelin-starred blend of French technique and Japanese ingredients. 9-course omakase.
Uraonikai Sushi – A 20-course omakase experience led by one of Tokyo’s rare top female sushi chefs.

Things to Do – Tokyo

Cat Board in Shinjuku – Catch the lifelike 3D calico cat stretching above Shinjuku Station
Omoide Yokocho – Wander the nostalgic alleyways packed with smoky yakitori joints
Kabukicho – Explore Tokyo’s wild red-light district, love hotels, arcades, and a looming Godzilla head
Kabukicho Tower Arcade – Play your heart out at multi-story arcades (don’t miss Taiko no Tatsujin)
Golden Gai Bar Crawl – Hop between tiny themed bars tucked into narrow alleyways
Tsukiji Market – Snack your way through Tokyo’s iconic seafood and street food stalls
Takeshita Street – Brave the kawaii chaos of Harajuku’s colorful, youth-driven shopping strip
Togo Shrine – A peaceful hidden gem just off the buzz of Harajuku
Kyu Asakura House – Wander this historic home and garden in the middle of stylish Daikanyama
Shibuya Crossing – Experience the iconic scramble surrounded by glowing billboards
Shimokitazawa – Spend hours thrifting and people-watching in this bohemian, vintage-lover’s dream
Tokyo Tower – Take in sweeping views, then stroll the surrounding park for a peaceful moment

Shopping – Tokyo

Kindal, Flamingo, WEGO, DESERTSNOW, 2nd Street – Explore impeccably curated vintage stores across the city
Visvim, Overchord, Traveler’s Factory, 1LDK – Shop for beautifully crafted goods in Nakameguro and Daikanyama
Don Quijote – Lose yourself in Japan’s wildest discount store (J-beauty, snacks, souvenirs, and chaos)
Family Mart / 7-11 – Stock up on shockingly perfect plain white tees and God-tier snacks.
Onitsuka Tiger – Iconic Japanese sneaker brand blending vintage athletic style with modern streetwear cool.

Kyoto Hotels

Campton Kiyomizu – A beautifully restored machiya tucked in Kyoto’s historic Higashiyama district, just steps from the Yasaka Pagoda.

Kyoto Restaurants

Cheap Eats
Nishiki Market – A bustling food hall filled with street food stalls and Kyoto specialties. A snack lover’s paradise.
Gyukatsu Motomura – Famous for its grill-your-own wagyu cutlets. Multiple locations, but the few that take reservations are worth tracking down—otherwise, prepare to wait.
Omen Shijo Pontocho – Widely considered one of Kyoto’s best udon spots. No reservations, but the line moves fast.

Cafes & Bars
Walden Woods – A serene, all-white coffee shop that feels like sipping a latte inside a cloud.
K36 Rooftop – Perfect sunset cocktails with jaw-dropping views of the city and surrounding mountains.

Fancy Meals
Gion Mametora – Traditional kaiseki served in a historic tea house. You dine in private tatami rooms with impeccable presentation. The ambiance is the main course here.
Arashiyama Itsukichaya – A hidden gem in Arashiyama with a 7-course lunch set and interactive food prep. Gorgeous river views. Easily our favorite meal of the trip!

Things to Do – Kyoto

Yasaka Pagoda – One of Kyoto’s most iconic landmarks, this five-story pagoda towers over the historic Higashiyama district.
Higashiyama & Gion – Walk through Kyoto’s most charming neighborhoods full of wooden storefronts and lanterns
Arashiyama Bamboo Forest – A serene path through soaring bamboo, best experienced early or during off-peak hours.
Saga Toriimoto Street – Wander a preserved street of grand wooden homes and historic quiet
Jojakkoji, Gioji & Adashino Nenbutsuji Temples – Temple-hop in Arashiyama surrounded by nature and peace
Kiyomizudera Temple – Kyoto’s most famous temple, with sweeping views and dramatic architecture built into the hillside.
Ju-An Tea Ceremony – Learn the traditional tea ritual at a serene local temple
Kintsugi Workshop with Wabunka Japan – Repair pottery with gold and take home your own work of art
Kōdai-ji Temple – Stroll through elegant Zen gardens and a hidden bamboo grove with zero tourists

Shopping – Kyoto

Ninen-zaka Marun – Pick up delicate sushi-shaped sweets that are (almost) too pretty to eat
Nittodo Kyoto Café – Grab sleek thermoses and beautifully packaged beans for gifting or keeping
手作り箸工房 遊膳 祇園店 – Shop for artisanal, hand-made chopsticks in the heart of Gion