10 Days in Japan: The Perfect Itinerary


If there is a single drop of water falling from the sky in Japan, every person has their umbrella out before it hits the ground. It is one of the cleanest countries I have ever visited, yet in the nine days I spent there, I saw no more than four garbage cans. Mainly I loved how safe it felt there. It was easier to be present to my environment, and to my thoughts, without worrying about my pockets getting picked, or an explosion in the train station. I felt at ease and free. 

For as hard as Japanese people work, they never seem to be in a hurry. No one pushes you in passing, or cuts in line, or loses their patience. The people are polite. Things work properly. Very refreshing.

A lot of travelers don't go to Japan because it has a reputation for being expensive. But there are plenty of budget options for both accommodation and food, and those options are far superior in overall quality to budget spots in other countries, relatively. Train/subway tickets definitely add up, but that's a small price to pay for a transportation system that functions as dependably as Greenwich Mean Time.

The harmony of old and new, ancient history and modern technology, almost makes it feel like you're getting two places in one. I've created this detailed synopsis (15 months overdue--thanks for your patience!) of my itinerary with my exact route, restaurants, and hotels. Use this as a guide to plan your own dream trip to this dynamic country.

DAY 1 - 4/6/16 - TOKYO

My sister arrived first and was waiting for me. I met up with her at the Hilton Tokyo. I chose this hotel for my first night because it's only a 15-minute walk from the main Shinjuku train station. (I almost always choose larger chain hotels for the first and last nights of my trips, and get more creative in the middle of a trip.) 

To combat jet lag, we left the hotel as soon as possible and walked to Yakitori alley, formally known as Omoide Yokocho ("Memory Lane"). It's the ideal option for cheap street eats. The yokocho experience is a perfect way to hit the ground chowing in Tokyo. Drinking Asahi and chomping on chicken skewers at a restaurant barely bigger than my home closet provided my first official "Holy shit, I'm in Tokyo" moment. (Don't bother showering before coming here; you'll reek of cigarettes at the end of the night.)

We meandered through Kabuchiko, Shinjuku's red light district. Blinding, towering neon, just what I wanted to see on my first night!

I couldn't miss Golden Gai, a grid of impossibly small bars (more accurately, drinking dens) stacked on top of each other like Leggos. It's known for being a seedier stronghold within Shinjuku, and choosing a bar is a bit intimidating. Some are very exclusive and the bartenders will give you a stink face before you can even check for an open chair. We found a sake spot on the ground level. 

Golden Gai

So much awesomeness in just the first few hours in Japan!


The next morning we left Tokyo for Kyoto. It was hard to leave so soon after getting a glimpse of Tokyo's electric nightlife, but we wanted Tokyo to be the grand finale of our trip. Something to consider is flying into Osaka (closer to Kyoto) and out of Tokyo, but since we flew in and out of Tokyo and had to take the train to Kyoto eventually, we decided to go straight there. 

It was raining, so we opted for the best fair-weather activity: Nishiki Market. Find the soy milk donuts and exotic dried fruit stalls.

There are many ceremonial tea houses in Kyoto. We chose Tea Ceremony Camellia, a short walk from Nishiki, primarily based on location and TripAdvisor reviews, although I get the sense that they're all fairly similar. It was certainly a welcomed respite after being on my feet all afternoon. I found the ceremony slightly gimmicky and rehearsed, but it was fascinating to learn how matcha is traditionally brewed and served, and I've been referring back to the lesson lately as I prepare my own matcha at home.

First temple alert: Kiyomizu-Dera. It's one of Kyoto's largest and most popular temples with a great view of the city. I enjoyed being there at dusk. Pro tip: bring extra snacks from the market!

Dinner recommendation: Omen. World's Best Udon? You tell me. 😋 

We stayed at Lower East Nine Hostel for all three nights in Kyoto. It's a gem of a hostel. Barely over a year old, impeccably clean, and very conveniently located (nearest train station: Kujo). I generally think of hostels as relics of my younger backpacking years and much prefer hotels to smelly dormitory rooms, but for peak season, and given the fact that I was traveling with my sister, Lower East Nine was a perfect choice for us. Delicious matcha lattes to boot.

DAY 3 - 4/8/16 - KYOTO (NORTH)

This is the secret to sightseeing in Kyoto: get an early start!

We woke up at 7 and tried to leave the hostel no later than 8 every morning. This strategy paid off at Nanzen-Ji, the headquarters of Rinzai Buddhism. Beyond serene and atmospheric in the morning calm. I particularly enjoyed wandering into a small cemetery in the back right corner of the complex. Having the place mostly to ourselves in the early a.m. made for a tranquil, meditative experience.

Now...prepare for chossoms. Cherry blossoms. Sakura. Lining the riverwalk known as the Philosopher's Path.

(Heads up: What Google Maps calls the beginning of the Philosopher's Walk is not actually the beginning; it starts before that, so pay attention on your way from Nanzen-ji.)

After months of stressing about the cherry blossoms, and trying to time our trip to maximize sakura viewing potential, I was pleased to reach the Philosopher's Walk on the most exquisite day for cherry blossom viewing imaginable. 

Since I started planning this trip six months ago, it has been all about the cherry blossoms. We tried to time it as best we could to hit peak season, but in the days leading up to our trip, the forecast said the blossoms were already falling, and I worried I might miss them altogether. Today, Sara and I walked the Philosopher's Path, and "Chossom Seez" put on one of the most extraordinary shows I have ever witnessed. It was snowing petals. There were fish and ducks drifting in them. There were couples getting married. There were artists painting on bridges. It was the most peaceful stroll I've ever taken. If you've been following me for a while you may remember the name Burton Holmes from quotes I've shared. He is one of the first and greatest travel documentarians. Listen to what he had to say about the cherry blossoms in Japan. I can't say it better than this: "The cherry-trees, which for eleven long, long months have stood like ugly skeletons, their denuded bones outlined against the sky, put forth quite suddenly a wealth of rosy blossoms, as if to say, "See what I have been secretly preparing. Is not a fortnight of this glory better than months of simple verdure?" Indeed, the very briefness of the season during which these flowers make the city glad, gives the cherry blossoms that charm which only evanescent things possess. Who would not willingly wait a year to see an avenue of trees all glorious with sunset clouds at mid-day. Japan needs no printed calendar; her people trace the progress of the seasons in these beauty-festivals that Nature plans and celebrates." 🙌🏽🙌🏽🙌🏽 My sister @sftrends is pictured. So fun traveling together again. #dametraveler #tltransportme #condenast #afar #traveldeeper #thepeoplescreatives #passionpassport #sakura #hanami #kyoto #cherryblossoms #springtime #travelstoke #passionpassport #elcaminotravel

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Jisho-ji, known by its unofficial name Ginkaku-ji (the Silver Pavilion), is certainly worth a visit if you're already strolling along the Philosopher's Path or exploring East Kyoto. But like most temples during high season, this place gets uncomfortably crowded at mid-day. When I visited at noon on April 8, it was mobbed, and I felt like a lemming mindlessly following hordes of tourists around the loop through the complex. Again: come early for proper Zen serenity. In any case, there's a silky view of Kyoto from the highest segment of the path, and the grounds are lovely.

Lunch recommendation: An Okinawan restaurant called Goya. As I recall, it was just a couple blocks from the end of the Philosopher's Walk. Funky, casual place, but the food was on point. I never thought I'd say this but: I recommend the bitter melon and tofu stir fry with a side of pickled sardines.

We took a bus to Kinkaku-ji, The Golden Pavilion (yes, the gold and silver pavilions differ by one letter--have fun trying not to confuse them). It was so crowded I found it unpleasant. The temple itself is extraordinary, but the tourist factor kind of ruined it for me.

Same is true for nearby Ryoan-ji--the rock temple. The thing to do here is look at rocks.

Or rather, the space around the rocks.

More precisely, the space emitted and inhabited by the rocks.

Relinquish your attachment to the rocks.

Be the rocks you wish to see in the world.

*SPOILER ALERT*: The rocks don't move.

Dinner recommendation: anywhere in Pontocho Alley. 


DAY 4 - 4/9/16 - KYOTO (South/West)

If there's one day I'm happiest I woke up early, it was this day, to see the iconic orange torii gates at Fushimi-inari Taisha. When we entered we were nearly alone. We could take pictures in the orange tunnels with no one else in them. A few hours later, as we exited, the impossibility of taking the same unobstructed photo was laughable. Mobbed! But no matter what time of day you visit, I'd recommend climbing all the way to the top of the mountain.

Next we headed to Maruyama Park for our first real hanami (cherry blossom viewing) experience. There were mostly locals in the park, drinking on mats and blankets under the trees. The festival-style food there was the worst I had in Japan, but drinking beers with my sister at Chossom HQ was really fun.

A 15 minute train ride out of downtown Tokyo, the Suntory Yamazaki distillery is worth it for whiskey connoisseurs and classy drinkers. Factory tours fill up well in advance, so check their website a month or two before your trip if it's really important to you. (Apparently some Japanese celebrity/whiskey guru had a reality television series touting Yamazaki, which spurred an influx of rosy-cheeked visitors.) Honestly, I would pass on the tour and go straight to the tasting room. You must taste Hibiki 17! Surprisingly, the shop had none of the premium bottles for sale, but (pro tip!) remember your favorite and pick up a bottle at duty-free in Narita. Your buzzed train ride back to the city center will be better, as usual, with snacks.

DAY 5 - 4/10/16 - KYOTO (ARASHIYAMA)

This was a perfect day. I mean that with no exaggeration. It was a flawless day of travel and life. It was a combination of planning, timing, and luck...

First stop: Arashiyama Bamboo Grove. I mayyyyy have snuck through a hole in the fence to get this shot:

At the back end of the path through the grove is the entrance to Okochi Sanso, the former estate of a Japanese actor--and Zen wonderland.

I'll never forget the experience of observing water dripping here, out of a bamboo stalk into a pond. It was not your ordinary dripping water! My advice for all the temples and gardens in Kyoto, especially Okochi Sanso, is to treat them as practice in listening, in stillness, in appreciating the present moment. So many tourists just march along the path from the entrance to the exit and leave. But I promise, if you listen--I mean really listen--to the water dripping, you will feel something you have never felt before.

Finishing the meander through the grounds with a cup of matcha was utterly delightful.

Reversing back through the bamboo grove we arrived at Tenryu-ji, another immaculate temple with stunning gardens. Worth the price of admission, especially since it's right there at the entrance to the bamboo grove.

From there we strolled along the river, stopping at Arabica Coffee, the most hipster coffee joint in Japan, and perhaps the entire world.

We had udon for lunch at a restaurant called Arashiyama Yoshimura. We were starving at this point and chose the place mainly for its convenient location at the Arashiyama bridge (real name: Togetsukyo Bridge), but it was some damn good udon.  

Here's my sleeper pick for best attraction in Kyoto, and maybe all of Japan:

Saiho-ji, a.k.a Kokedera (The Moss Temple), a UNESCO World Heritage Site.

This is one of the most unforgettable/spiritual places I have ever been.

It's a Rinzai temple with an ancient moss garden, protected by a moat inside of a gated complex. The moss is supposedly a remnant of a flood in the Edo era and considered sacred. 

You can walk to the temple (kind of far from the bridge; consider a bus), but you can't just walk in. You have to make a reservation in advance--via...wait for it...snail mail! Meaning, you have to write a letter to the temple and mail it to them. OR you can do what I did and use this service

For a small fee, they communicate with the temple on your behalf, procure the tickets, and deliver them to your hotel in Kyoto. It worked perfectly for me. 

A huge part of the experience of visiting Saiho-ji is copying sutras, which is a surprisingly grueling prerequisite for entering the moss zone. You have to sit on your feet at miniature desks and copy hundreds of intricate Japanese characters with a thin paint brush. I was about 6% finished with the sutras when I lost all feeling in my legs. No one tells you you have to finish, but...I wasn't going to be the guy who didn't finish!

All of my modern-day American habits and tendencies were exposed--the rushing, the complaining, the comparing. The whole point of the activity, however, is to simply DO the activity. And doing it made me appreciate the moss even more. 

We ate at a local joint near the entrance of the temple, took a bus back to central Arashiyama, ate matcha ice cream, shopped for ceramics, and watched the cherry blossom petals swirling in the breeze. 

After all that Zen training and all those temples and all that beauty, to cap it all off, we saw two Maiko (geisha-in-training) crossing the bridge. Show me a more perfect day!

DAY 6 - 4/11/16 - NARA

Train to Nara...

Since we weren't sleeping in Nara and obviously didn't want to explore the city with luggage, we stashed our bags in a locker at the train station. (This tactic also came in handy in Tokyo a few times.)

The giant Buddha at Todai-ji is the biggest attraction, besides, of course, the deer, which are everywhere, but least annoying in Nara Park.

I also enjoyed the view from another temple called Nigatsudo, next door to Todai-ji. 

Definitely see the lanterns at Kasuga-taisha.

We ate bagel sandwiches for lunch at The Deer Park Inn. A bagel with avocado on it was much appreciated after my twelfth bowl of noodles.

If you're not totally Zenned-out from temple hunting in Kyoto, Isuien Garden is one of Nara's loveliest. There's also a tea room on the grounds that serves food (on tatami mats). 

If you're sick of paying for gardens, there's a free one right next to Isuien called Yoshikien. It's not that amazing, but still a peaceful place to stroll. 

We spent the night in a Buddhist temple 17 km outside of Nara. This is what I was talking about when I said I get "more creative" in the middle of a trip.

The temple is called GyokuzoinIt's 17km outside of Nara and requires a train and taxi to get to. But as far as unique accommodation goes...

As I described in my original Instagram post about this place, "Imagine an upscale ski-lodge somewhere in Mongolia in the early 1970s. That's what the lobby looked like."

Waking up at 5:00 a.m. to watch the monks perform their daily fire ritual was the highlight of the whole stay. Dressing up in yukata for a traditional kaiseki dinner was also quite memorable. 

Bonus points: there's an onsen at another hotel within walking distance that Gyokuzoin guests can use. I befriended a Swedish dude at the temple and within an hour we were bathing nudely together in tub of tepid water. That was interesting.


This awkward extra day was the hardest segment of the trip to plan. I considered going to Osaka. I considered going to Hakone. I considered everywhere that I could spent one night, and see something new, without going out of the way in my attempt to get back to Tokyo. 

I chose to visit the Fuji Five Lakes region. If I could do it again I probably would have burned that day traveling all the way back to Tokyo and stayed an extra night in the city. 

But seeing Mt. Fuji had been a dream of mine for a long time.

We stayed at a fancy onsen hotel called Rakuyu, overlooking Lake Kawaguchi, which was extremely comfortable and one of the plushest places we slept on the whole trip. 

I made the pilgrimage (train ride and about 1,000 stairs) to Chureito Pagoda, which mostly validated the entire Fuji detour. (If possible, go at sunrise--the mountain tends to be a lot clearer in the morning). 

Mt. Fuji was just a little bit too out of the way. It took two train rides and a bus, as I recall. And when we got there we couldn't help but think, "I wish I was in Tokyo right now."

So the next morning, we got on the first train to Tokyo.


It wasn't convenient to take our bags all the way to our hotel, so we stored them in the Harajuku train station and set out to explore.

Takeshita Street is where you're most likely to find Harajuku girls. It's the younger/alternative area. Omotesando is the main shopping boulevard. I particularly enjoyed the streetwear stores on Cat Street.

We ate at a quirky restaurant called Rainbow Pancakes. Someone else recommended it to me. The food was good, but it was more about the oddness of the ambiance. Expect a line. It's what the name suggests: rainbows. And pancakes. (There are sickeningly sweet and healthier/savory options.) 

My advice for a first afternoon in Tokyo is the same as my advice for a first aternoon in any city: walk! Walk everywhere. Get lost. Buy a fancy shirt at Comme de Garcon. Or maybe just browse, because you probably don't need a fancy shirt at Comme de Garcon.

We walked to Shibuya crossing. We crossed. It was awesome. The Starbucks is a good place to shoot a timelapse.

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But I found a better view from the Excelsior Hotel:


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For a truly exceptional dining experience in Tokyo, try Jimbocho Den. It's a 1-star Michelin restaurant...with six seats! Every course was an experience. Start trying to get a reservation NOW.

Instead of staying at a modern hotel, we opted for a traditional ryokan called Ryokan Sawanoya in Ueno. It's astounding that you can find a quiet, old-style guest house like this in the middle of Tokyo, only a short walk from the nearest train station (Nezu). If you're not tired of sitting cross-legged or sleeping on tatami mats, I recommend this place for an affordable alternative to a snazzier chain hotel. It's quaint, but I always felt happy and relieved to arrive back here at the end of a long, buzzing day in Tokyo.


This was technically our first full day in Tokyo. It was one of my favorite days of the trip because it was one of the most open-ended, and we were finally comfortable navigating the city.

We started at Tsukiji Fish market, perhaps most famous for its daily tuna auctions, which happen in the early, early morning. You can watch the auctions but it involves waking up at ~4:00 a.m., and that just wasn't going to happen for me. But I heard it's quite a spectacle.

The market is scheduled to change locations to an artificial island not far from the current location. I believe the move is currently estimated for Winter 2017.

In the "old" location I thought I had seen the entire market, then I realized there was a whole other section packed with all the best sushi restaurants. So...find that!

It's easy to spot the best restaurants. Lines galore. But no matter where you eat, the sushi will be incredible.

Most of this day was spent at a jewelry store in Ginza called Mokumeganeya. I was buying my wedding ring! Mokume-gane is a Japanese metalworking technique that involves layering metals into wood-grain-like patterns. Maybe check it out if you like jewelry.

Ginza is where all the upscale fashion stores are located. There's also a famous tempura restaurant in Ginza called Tempura Kondo.

Barack Obama was rumored to have been declined a seat there. It was full, and the owner (Kondo) wouldn't boot any of his reserved customers to make room for the Pres.

I especially love this story because my sister and I stumbled in looking for any old lunch spot, not realizing how expensive it was, and two people had cancelled at the last minute. We obviously had to fill those seats!

All the other patrons laughed at our lucky entrance. I laughed at myself for eating at two Michelin restaurants (this one is 2-stars) back-to back. Just like at Den, you sit at the counter, and Kondo himself reaches over to serve you with a glimmering super-sized pair of tongs. It was the best tempura ever. 

One thing that had been missing from our Tokyo experience thus far was, as I call it, "the weirdness." That bizarre, Lost In Translation, only-in-Tokyo sensation. We had glimpsed it, but finally got a full dose at Forest of Owl owl cafe. There are many owl cafes in Tokyo, and I get the sense that they're all similar--similar in that there are OWLS EVERYWHERE. Trippy!

Forest of Owl is located in the arcade district of Akihabara, which is like Times Square on robot-crack, plastered with manga, awesome and slightly terrifying. 

We walked all the way back to our ryokan, stopping for dinner at a Yakiniku restaurant (you grill your own meat). I don't remember the name of the restaurant but I did enjoy cooking cow tongue at my table.

Strange but fantastic day!


I always go hard on the last day of a trip. 

We started in Asakusa, but temples had kind of lost their luster by this point, so we didn't spend much time at Senso-ji

We considered going to the top of the Tokyo Sky Tree, but waiting in line for two hours was not the move, so we bailed on that plan.

I was determined to find an elevated view of the city, so while my sister was at a business meeting (what kind of Boss Lady has a business meeting in Tokyo while she's on vacation?), I set out for Tokyo City View at the Mori Art Museum in Rappongi Hills.

It was closed for a private event! I was bummed! 

Based on how awesome the gift shop was, I imagine the museum is worth a visit. Based on Google images, the observation deck definitely is. 

I reconvened with my sister at Gen Yamamoto, a cocktail bar completely unlike a typical bar. It's one cocktail wizard (Gen) in a white lab coat mixing minimalist drinks at an unadorned oak bar. The guy is clearly an expert in his artful yet fairly pretentious approach to making drinks.

The whole experience felt very sophisticated and intimate, but when I walked out of the tasting feeling barely buzzed after four cocktails, I realized Gen Yamamoto was more about the presentation than what I was interested in, namely Turning Up on my last night in Japan. 

Our next stop had no shortage of alcohol. It was Ebisu Yokocho (yokocho means "alley" or "lane"; there are many different yokochos around Tokyo). This place was hilariously hard to find. We were standing at the door, looking as hard as we could for it, and still couldn't find it. We walked around the entire block. No Ebisu Yokocho in sight. Finally we saw someone slide open a narrow door. It was the block. We lapped the place and still couldnt find it!

When we finally entered it was like entering real Tokyo, with locals eating the local way. Mainly, I couldn't believe we hadn't heard the ruckus from outside. It was a scene in there! It's hard to distinguish where one restaurant ends and another begins. We ended up eating at a mushroom-themed booth and inadvertently joining someone's birthday party. This was shaping up to be a helluva night...

We continued the party at an absinthe bar called Bar Tram. Perfect post-yokocho venue. We were preparing to stay out all night but didn't have a plan, so we asked our waitress for recommmendations. She said her boyfriend was a DJ and was playing a show nearby. She gave us the address. We went there. It turned out to be a rave. We stayed. Tokyooooooo!!!!

We slept at the Hilton Shinjuku rather than the ryokan on our final night. They lost money on me when I hit the breakfast buffet. And then a very sad thing happened...

DAY 11 - 4/16/16 - TOKYO / SEATTLE

We went home.

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