Intro

Shikoku is the smallest of Japan’s main islands, and the second of four I’m crossing on my cycling trek across the country. It took just five days and 266 miles, barely a tenth of my total route, yet I find myself returning to it far more often than its share of the distance would suggest.

This is a dispatch about the week I spent navigating the heart of Shikoku’s rugged interior by bike. It’s not a comprehensive cycling guide, just an attempt to capture some of what made this island so beautiful and special.

Route design notes are in an earlier post, and GPX recordings are here for anyone who wants the data.

Turning Inland

After a rest day spent hopping between the famous Hells of Beppu on Kyushu’s northern coast, I boarded a morning ferry bound across the channel and towards the next island in my journey, Shikoku. I disembarked a few hours later in Yawatahama, more of a small fishing town than the flashing-neon-pachinko-parlor laden tourism city I had left behind earlier that morning.

Unlike most cyclists arriving on Shikoku, I was not there to ride the Shimanami Kaido. This is one of the most famous cycling routes in Japan, and for good reason: spectacular scenery through Setonaikai National Park, following well-supported cycling paths along massive suspension bridges as it hops through a chain of islands connecting Shikoku and Japan’s primary island of Honshu. When designing my route across Japan, I decided to trade a traverse of the Kaido for the opportunity to travel deep into Shikoku’s interior. I’d be swapping the Kaido’s well-trodden cycling paths along coastal plains for something with less margin for error: remote mountain roads, long stretches without services, some of the largest cycling climbs in all of Japan, and a route going through parts of the island rarely visited by cyclists.

Riding out of the dark hold of the ferry and into the bright afternoon sunlight, I placed the dark green wall of the island’s mountainous interior in front of me and began the day’s ride. With 3,500 feet of climbing over a steep 40 miles, the purpose of this ride was to get deep into Shikoku’s interior in order to effectively stage for the main event of the island: a traverse of the spectacular UFO Line and some of the highest roads on Shikoku.

Ascending into the mountains, the footprint of Yawatahama thinned out quickly. Four-lane highways narrowed to two lanes and then to one, sidewalks and vending machines disappeared, and vehicle traffic dropped to almost nothing. The rice paddies I’d grown so accustomed to during my traverse of Kyushu gave way to raw forest which seemed to envelop the roads as I spun along in low gear. After a few hours of cycling, I began passing a new sight for this trip: people walking along the side of the road, with small backpacks, straw hats, and wooden walking sticks. I soon figured out they were pilgrims of the Shikoku Henro, trekking 750 miles between the 88 Buddhist temples which span the length of the island. Shadows grew long across the road as I resisted the temptation to explore every passing curiosity and tried to maintain momentum along the steep climbs.

Arriving into the mountain town of Kumakogen around nightfall, I detoured past two dark “supposedly open” restaurants before settling for a konbini dinner of onigiri and croquettes at the town’s FamilyMart. This specific FamilyMart would be the last convenience store I’d see for the next 80 miles of cycling, unbelievably sparse by the standards of Japan, and so I loaded up on calories accordingly. I departed with my jersey pockets stuffed with chewy candies, canned coffees, and IN Energy gels, and a collection of non-perishable cake-like treats lashed down haphazardly to the exterior of my cycling bags. Rushing through this final climb to maintain body temperature in the cooling forest, my hotel appeared out of the dark woods as the first illuminated building I’d seen in the miles since leaving town. I checked into my room, one still boasting of the countless cigarette smokers it had hosted since the hotel was built in the Shōwa era, quickly gave up the task of uploading footage after seeing the hotel’s WiFi was operating at speeds also era appropriate, and knocked out quickly in anticipation of the next day.

Subscribe now

The UFO Line

Moving slowly through the first cold morning I’d experienced since landing in Japan a few weeks prior, my intended 7am start slipped first to 8am and then 8:30. I forced down enough electrolyte drink and cream cake to kick off a small bout of nausea in the hotel parking lot before continuing my trek into Shikoku’s interior. After 45 minutes of quick movement along undulating roads a notification popped up on my cycling computer — starting climb: 22 miles, 7,100 feet of elevation gain. That caught my attention.

I was starting my ascent to the UFO Line, a 17 mile stretch of exposed road which hugs the central spine of the island, popular with driving enthusiasts for the road quality and the views it provides in all directions. Ascending to this line would require completing the largest climb I’d ever attempted, and I estimated I’d make it to the summit around 2pm if I managed to maintain momentum. This was relevant because the end of the UFO Line marked only the halfway point of the day, and I needed to make it 72 miles to my hotel by 8pm or risk finding out what precisely was meant by their “latest possible check-in” policy.

A few miles into the climb, I stopped on the side of a bridge to rest while taking in the scenery when a rare passing motorcyclist stopped right in front of me. Expecting a potential scolding from a local for partially blocking the road, I was greeted instead by a friendly smile and a “hello!” in a vaguely German accent. Boris was on leave from his job and rented a motorcycle to travel across Japan for a few weeks, starting in Tokyo and looping around the southern islands according to no itinerary in particular. We talked about aspects of Japanese society that westerners tend to single out for appreciation (cleanliness and high baseline trust, namely) before moving onto a discussion about work, savings, vacation, and travel. He was happy to hear about my decision to quit my job, and expressed joy at the idea of me having three months to wander the country by bicycle without much of an idea as to what would come next in my career. The conversation meandered through the classic travel topics; the purpose of saving money, how to find more time to travel in a busy life, and how quitting a job can feel scary in the moment but is rarely a mistake in hindsight. He drove off after a firm handshake and genuine well wishing, quickly receding into the distance at speeds I could barely dream of while I picked up to a laughably slow 5mph and continued my climb.

I rounded the first summit a bit after 2pm, drenched with sweat on an otherwise chilly day and a bit delirious from the sheer volume of energy my legs had expended over the last few hours. I spotted a Montbell store with an “open” sign dangling in the window and wandered over, hoping to partially replenish the calorie stash which I had entirely emptied during the ascent. Expecting to maybe find a small selection of Cliff Bars, I was instead greeted by an active food counter selling hot coffee, cold beer, and hot dogs made of local deer meat. I devoured two hot dogs to start, and then a third, while staring out at the landscape through the windows, still surprised my body was actually able to complete the climb. I would have been content to sit there for the rest of the afternoon taking part in what could be described as the world’s least exciting hot dog eating contest, but I was keenly aware of the afternoon slipping away and my arrival deadline approaching. Soon after leaving, I crossed through an open gate and over the giant characters “UFOライン” painted on the asphalt, marking the official start of the UFO Line itself.

The road widened a bit and the surrounding forest dropped below the railings as views into the distant reaches of the island opened up in all directions. Except for the handful of local mountain peaks jutting off of the line itself, all I could see were nested layers of forested ridge lines, each devoid of any signs of human activity. No farms, no hotels, no ski lifts or other pieces of modern infrastructure, just raw Shikoku forest. Not since starting my cycling trip at the southern tip of Kyushu had I had this uncanny sense of embodying a moment I had spent so much time thinking about. Here I was, gliding along this famous ridge line, awash in the satisfying sense of rugged solitude earned under my own leg power.

After an hour-long traverse, I rode across another set of large characters painted across the asphalt. This marked the end of the UFO Line and the start of the back half of the day — 5,000 feet of descent across 30 miles of roads winding even deeper into the island’s interior. This would be not only the longest descent I’d ever done on a bike, but the longest descent I’d ever even heard of in my cycling career. I expected it to be a just reward for the brutal climbing it took to make it here from the coastal port of the previous morning. The descent was comically long, and the initial relief of not needing to pedal gave way to pain in my hands and forearms as I rode my brakes hard to manage speed. The initial joy of exchanging hard-won potential energy for quick forward progress was replaced with mental fatigue from needing to analyze the oncoming path for obstructions, washouts, and potholes.

To the relief of my forearms and brake pads, the road gradually leveled out as I left the heights of the ridge line and descended into the surrounding valleys. I eventually turned off the forest road I’d been following all day and onto Highway 17, an official-sounding name for a single-lane road that greeted me with rusted road signs and abandoned buildings. The road clung to the wall of a river gorge for the next 20 miles to Motoyama, separated from the water below by guardrails of questionable integrity.

As I progressed, tributaries joined the river and the gorge opened deeper around it. Boulders, large enough to induce a sense of vertigo when stared at, dammed parts of the river, and the vegetation line 30 feet above the water hinted at the incredible floods this place must see in wetter seasons. Rusted outcrops of collapsed steel bridges and old tunnels, remnants of previous versions of this road, peeked out from beneath the forest’s slow reclamation. The landscape here was as lush as anywhere I had ever been, and I bled precious time from the late afternoon by stopping to marvel at the myriad waterfalls spilling off of the high cliffs and into the depths of the gorge.

By then, the energy from the deer hot dogs was long gone. The day started announcing itself through my sore muscles, aching contact points, and increasingly sloppy focus, and every photo stop became a little harder to restart from. This moderate, picturesque downhill somehow felt more taxing than the headliner climb from that morning.

After a grueling last hour coasting via headlight and counting down the passing fractions of mileage left, I arrived at the check-in desk for my cabin just before cutoff. I was wearing every one of the 72 miles of cycling in expressions of exhaustion on my face and slight grunts of pain as I waddled through the lobby. The polite hostess at the desk pretended not to notice how close I was to missing my deadline and checked me into my room for the evening as if nothing was amiss.

Technical note — the climb ended up being 5,500 feet and not 7,100. My cycling computer lacked knowledge of a few tunnels which cut through, rather than over, mountain ridges.

Oboke Gorge and Iya Valley

I awoke in Motoyama to housekeeping knocking on my door. I had accidentally forgotten to set an alarm before passing out and my body was more than prepared to sleep until noon if not for this disturbance. After rushing to collect my things and change into cycling clothes, I stepped outside to the sight of rain blanketing the town. This was not my ideal morning.

I slowly booted up at a local cafe over two flat whites and as many slices of cheesecake through late morning and finally came to accept the fact that the rain was not letting up any time soon. My short jaunt down the valley would be done in fogged-up glasses and wet cycling shoes.

The 20 mile trek led me to Oboke Gorge, a collection of buildings more resembling a fancy rest stop than something most people would consider a town. The last few days of cycling had caught up with me and I was running a laundry, protein, and sleep debt, so I’d be checking into an onsen hotel for a rest day. I stopped at a cafe/restaurant across the hotel while awaiting the check-in window to open and ordered my first hamburger of the trip. Sitting down at a counter to dive into my lunch, I was forced to do a double-take by the view stretching out in front of me — the actual gorge for which the area is named. This section of the Yoshino river slows and widens dramatically as granite cliffs hem it in on both sides. Above it, a wall of sopping tropical vegetation lifts clean to the ridges high above, the mass of green broken only by the vague outline of a JR train passing through the valley twice an hour. I regretted expending the grandest of adjectives on the gorge of the previous afternoon, which now seemed diminutive compared to the shining glory that was Oboke dropping out in front of me.

3pm rolled around and I checked in to my hotel just down the road, delighted to find the gorge visible from my room. Even more delightful, I ventured to the sub-level of the hotel to use the onsen and found the open-air hot spring built into the cliffs overlooking the gorge. The onsen is far enough below the road to prevent pedestrians from seeing the naked bathers while providing 180-degree views of Oboke’s rushing waters after the full day of rain. I rotated through the sauna, cold-plunge, hot-spring, lounge cycle for the better part of the afternoon before turning in for an embarrassingly early bedtime.

There’s really only one reason why most people come to this area, which is to go on a boat ride through the gorge itself. While looking out of my hotel room window, I saw a steady stream of charter buses unloading tourists in a parking lot at the top of the gorge, where they would line up single-file and descend a long staircase towards the river. Being something of a tourist myself and with an entire rest day on my hands, I decided to partake in the local tradition and venture down to the river’s edge. I was shuffled onto a boat, donned a life jacket, and was serenaded by the odd combination of an insufficiently-muffled motor and a loud tour guide talking the passengers through what I’m sure were interesting details of the gorge’s geology, though of course it was in Japanese and so I did not understand a word of it.

While trying to Google Translate a portion of the tour guide narration, a notification popped up on my phone: GPT-5.5 had just been released. That was the first time I’d been surprised by a model release since before joining OpenAI three years earlier, and was evidence of the intense work that my friends and former colleagues were carrying on in my absence. Memories flashed of the handful of releases I had participated in during my tenure, somehow simultaneously the most chaotic periods of my career but also the most memorable. I swiped away the notification and went back to the translation, which inevitably failed through the muffle of the loudspeaker and noise of the engine.

The sun came out the following day as I was leaving the gorge and I decided to detour through the neighboring Iya Valley rather than take the original direct route to the coast. This would more than double the mileage and climbing total for the day, but it was my last chance to see Shikoku’s interior and was the best weather I’d had in a while, so I decided to make the most of it.

Deciding to avoid a dance with traffic through the mile-long tunnel connecting Oboke and Iya, I instead started my day with a 2,000 foot climb on an old forest road traversing the mountain separating the two valleys. From the top of the climb I could see Iya Valley shining in the morning sun and started what would be an entire afternoon of warm and pleasant descending out to the coast.

I made a quick stop by the place Iya is most known for — Iya-no-Kazurabashi, the Iya Vine Bridge. This is a long footbridge spanning the Iya River, notable for the fact that it’s made out of foraged vines from the nearby forest and rebuilt every few years as the vines wear out. While I expected a gimmicky experience, the bridge’s height above the valley below and the way it bounced and swayed under the march of other tourists actually made the crossing somewhat exciting, and the construction of the bridge was more interesting to see in-person than I expected.

Before descending out of Iya to join the coast once again, I had one more routing choice to make. I could work my way back to the proper Highway 32, which would be direct, have plenty of services, and be the safest bet for leaving the interior. I had another option — Prefectural Route 32 — a sliver of a road which only revealed itself if you zoomed way in on the map. This was barely a single-lane wide, very winding, and showed evidence of recent closures due to landslides. It would almost certainly be devoid of traffic and would allow me to continue following the scenic Iya Valley all the way out of the mountains. Knowing I ran the risk of hitting a road closure and needing to backtrack, I went with a gut feeling that things would work out and descended along this prefectural route.

The hotel and restaurant footprint of the town quickly vanished and I was immediately tucked into the narrowest road I’d seen on the island. The dense forest buckled over the highway to my right, providing shade from the midday sun. The massive Iya Valley opened up to my left, exposing me to the warm breeze coming up from the lowlands along the coast. I put on a favorite album (Sound of Silver by LCD Soundsystem), settled into the saddle, and felt the uniquely satisfying sensation of starting a long descent which doesn’t end in another climb. I’d stop for the occasional point of interest — a special lookout here, a Buddhist temple carved into the cliff face there, even a semi-famous statue of a child urinating over the cliffs and surrounded at the feet by a pile of yen coins, but otherwise maintained steady momentum as the road worked its way slowly towards the level of the river far below.

Occasionally, you just get a fantastic day without caveats — no rain, looming hotel deadlines, or record-setting climbs. Just a smiling, sweating man and his bike.

Takamatsu and the Inland Sea

I pulled into Takamatsu tired, hungry, and later than I had anticipated. Despite the recent rest day in Oboke, I was absolutely smoked. The cumulative fatigue of not just Shikoku but the 800 miles of cycling I’d done since starting the trip just two weeks prior was catching up to me. Golden Week and six days off of the bicycle was just around the corner, but I decided to take a double rest day in Takamatsu to give my muscles the more than 24 hours they needed to begin recovering. I cleaned up quickly and ventured out into the downtown strip of Takamatsu for dinner, which began one of the more humiliating and confusing sequences of the trip.

Hungry and tired, I was rejected from five different restaurants in a row. I’d open the door, say "hitori desu” while holding up my index finger to signal I was alone, and would be flashed a large “X” made by the crossed forearms of the hostess. At first I thought the restaurants were potentially full, but the last three to reject me had plenty of seats open. While I never got a satisfactory answer (I didn’t want to ask the host to justify their rejection via Google Translate), my hunch is that most restaurants in the downtown strip don’t consider it a good use of space to seat a solo diner on a Saturday night? Exasperated and worried I was either committing some unfathomably grotesque faux pas or had some sort of new and contagious appearing growth on my face, I gave in and had a very sad konbini dinner. Rice balls, potato chips, cream cake, and a full-sugar coke in the hotel lobby at midnight.

Despite the rough start, the next two days were a bit more kind. Takamatsu’s famous Sanuki Udon provided the carb-loading base I needed for energy, while its excellent Ritsurin Garden provided a place to nap in the grass or read my Kindle from the tatami floors of an ancient tea house. I even found the willpower to wait two hours in line for a chance to try Honetsuki-dori, a famous chicken dish of the area. I managed to avoid restaurant rejections the remaining two days and ate meals that I’m still day dreaming of while writing this, a month after leaving Shikoku.

With my double rest day finished but my body only partially recovered, I departed Takamatsu and hobbled along the northern coast of the island. I was bound for the town of Tokushima, where I’d catch a sunset ferry for the next island of my journey, Honshu.

My route hugged the shores of the Seto Inland Sea, the same body of water the Shimanami Kaido traverses farther west. Riding along glass-calm water, with protected bike lanes and an abundance of services compared to the sparseness of the interior, I understood why the Kaido has become such a renowned cycling destination. Shikoku’s interior had given me exactly what I needed from this crossing: an ass kicking, a glimpse into the rugged center of the island, and a week of riding through places I’m unlikely to reach again by accident. But that short ride along the Inland Sea made clear that I had not exhausted Shikoku. I had only chosen one version of it, and someday I’ll need to come back and give the Kaido its proper due.

Northward

It’s been a month and over a thousand miles of cycling since I left the northern shores of Shikoku by ferry. I was worried that some of the texture and detail of the island would have faded from memory in that time, but this specific week in late April sticks out brightly in my mind. I think it’ll be a long time before I forget just how epic it felt to climb over the UFO Line, or the sense of awe that Iya and Oboke inspired.

Shikoku is where I confronted some of the toughest days of the entire trip. That I loved the remote interior, rather than merely surviving it, made me trust I could take on the hardest days still ahead. It’s what pushed me to rework parts of my northern Honshu route to venture even deeper into the mountains than I’d first planned.

I’m writing this from a cafe in northern Honshu, preparing to move on to Hokkaido and the last of the four islands I’ll cross on this trip. With less than 700 miles to go, the end is just barely coming into view. As is the case with the ending of any good thing, the temptation to pre-grieve it is already strong.

P.S. — I’m intentionally staying off of social media on this trip, but if you’d like day-by-day updates, you can find me on Strava uploading my daily rides along with some photos and commentary https://www.strava.com/athletes/33055758

I’m writing this from Osaka, where I’m taking a six day break off the bike to rest and recover before continuing north across Japan. I crossed the island of Kyushu back in mid-April, finishing the first of Japan’s four main islands in eight days of riding and a handful of rest days. At 380 miles and nearly 25,000 feet of climbing, it was a proper cycling trip by any reasonable measure.

I’ve been avoiding the temptation to write this as a day-by-day trip report. Instead, this is a dispatch from the first island, i.e. a handful of scenes and impressions that stayed with me as I kept moving north.

Route design notes are in an earlier post, and GPX recordings are here for anyone who wants the data.

Beginnings

The first sense of this trip’s beginning came the night before I left Tokyo, in a hotel room across from Shinagawa Station. After nearly two weeks spent enjoying the culinary and cultural comforts of the city, I spent the evening reassembling my bike and sorting my belongings into two piles: the things that would come with me, and the much larger pile that would not. At 9pm, a truck pulled into the hotel parking lot to collect all of those things that could not fit onto my bike. I handed over two suitcases full of clothes, toiletries, electronics, and other small comforts, then returned to my room which looked suspiciously tidy after the chaos of the last few hours. Against the far wall leaned my bike, its few bags entirely overstuffed despite the minimalism of my packing list. For the first time since dreaming it up so many months prior, the trip felt less like an idea and more like a physical fact. Ten weeks of movement, reduced to this one bike and what I could carry on it.

The next morning, after awkwardly wrestling 50 pounds of gear through the rush-hour train station, I boarded a Shinkansen bound for Kagoshima, the southernmost major city in Japan and the closest I could get by train to the start of my route. I settled into my reserved seat with a breakfast onigiri and canned coffee while the train cut through a country dense with rain. For six hours we moved at nearly 300 km/h, close enough to the ground to see fields, factories, towns, coastlines, and mountains, but fast enough that Japan slid by in an almost abstract manner. I had stared for months at the route as a set of colored lines on a digital map and knew the numbers by heart: 3,700 kilometers, four main islands, 49 planned days of cycling. From the train window, the scale finally became intuitive. This was the landscape I would have to earn back, slowly, under my own power, from the exposed saddle of my bike.

Six hours and 2,000 kilometers later, I left the Shinkansen station in Kagoshima and boarded a ferry across the bay toward the peninsula that holds Cape Sata, the southern tip of Japan’s main islands. After securing my bike among transport trucks and rental cars in the hold of the ship I ascended to the passenger deck, where the dark of the hold gave way to sunset. Tropical air greeted my face and the ferry rumbled beneath my feet as it pushed through the water of the bay. Kagoshima receded into the distance behind me while Sakurajima sent a plume of volcanic smoke blending into a cloudy sky off to my left. To my right, a line of volcanic silhouettes faded into the southward distance, the direction I would cycle into the next day. For a moment, the anxiety of logistics fell away: the train transfers, the weather checks, the bike assembly, the nervous first miles on the left side of the road. I was alone on a ferry at the southern end of Japan, the only person in sight dressed entirely in spandex, watching the terrain I had spent so much time tracing on maps rise out of the bay in front of me.

Eating Kyushu

A handful of interactions with locals during my first few days in Kyushu taught me that “Japanese food” was too broad a category to have much relevance on this trip. People would ask where I was riding next, then tailor recommendations to the route with surprising precision. Miyazaki had its beef and chicken. Kumamoto had its horse. Oita had its own specialties. Ryokan meals came with ingredients I never would have ordered on my own. These recommendations were delivered with the seriousness of people trying to ensure I did not pass through their part of Japan incorrectly.

By my fourth day of cycling, I had ridden roughly 200 miles through southern Kyushu and arrived in the city of Miyazaki exhausted, sun-soaked, and badly in need of protein. A quick search turned up a highly-rated yakiniku restaurant near my hotel. Locally raised meat, grilled at the table, with rice, kimchi, dipping sauces, and the possibility of ordering until my legs stopped complaining.

It sounded perfect, but truthfully, I was intimidated. My Japanese consisted of maybe twenty memorized phrases, five of which were apologies, and English speakers are rare on this side of the island. A high-interaction dining format like yakiniku seemed like the type of place where I was destined to make an ass of myself. I briefly considered giving up and heading to the local ticket-machine rice-bowl chain, but there is an optimal number of times to risk making an ass of yourself while traveling, and that number is not zero. One of these dinners had to be my first yakiniku night. It might as well be tonight.

I walked in, and surprisingly enough, the restaurant was empty. I held up one finger and bowed to signal my intention to occupy a grill by myself, then was pointed to a spot at the counter. Google Translate over a photo of the menu led me to a trio of locally raised meats: marbled short rib, pork belly, and chicken thigh. I struggled through an order for the combo, a side of rice and kimchi, and a non-alcoholic beer. The owner lit my grill, rubbed it with tallow, and a few minutes later placed a platter of raw meat in front of me.

I took a slice of the most marbled beef I’d ever seen in person and laid it delicately atop the grill, flipping it after a few seconds and erring on the side of rare since it would certainly be a crime to overcook meat of this quality. I gave it a quick dip in the house sauce, placed it on my tongue, and it melted. My body registered the abundance of calories, fat, salt, and protein and shivered in response. Two chews and the slice had dissolved. I genuinely did not know beef could be this good.

The next few hours followed the same pattern: grill meat, dip in sauce, alternate with rice and kimchi, wash it down, ask for the next recommendation, repeat. By 8 pm I was sweating from some combination of the charcoal grill’s heat and my body’s struggle to process the amount of protein I was ingesting. At some point, the owner became curious about what could possibly have worked up this kind of appetite, and I explained my trip: Kagoshima to Wakkanai, by bicycle. Other diners overheard, asked questions, laughed, and seemed delighted by the absurdity of it.

That night kicked off a string of culinary encounters across Kyushu: a heaping plate of chicken nanban in Takachiho Gorge, blackened charcoal chicken cooked in front of me in the Aso Caldera, a ryokan attendant in Oguni gently convincing me to try basashi while failing to overcome my deeply American suspicion of raw chicken. Beneath all of it was the daily rhythm of konbini calories: canned coffee, croquettes, onigiri, custard breads, fruit sandwiches, and at least one lunchtime ice cream bar, rain or shine.

Rain

I had spent the weeks leading up to this trip dreading the prospect of cycling Kyushu in real rain. In five years of cycling, I had never ridden in anything heavier than a drizzle, which is the kind of statement only a Californian can make with a straight face.

The weather broke in my favor for the first few days, but on the fourth morning I woke to dark skies and the sound of heavy rain against my hotel window. An updated forecast confirmed my suspicion: the day’s 65-mile itinerary up the Miyazaki coastline would be done in a downpour. I pulled on my never-before-used rain gear, triple-checked the seals on my cycling bags, and set off north. Within 15 minutes I was soaked: splash from puddles kicked up by passing vehicles, spray from my own wheels, rain running off my helmet and jacket and onto my absorbent bib shorts. Within 30 minutes I was wet in places I had not expected to be wet: inside my gloves, inside my cycling shoes, underneath my rain jacket.

I stood there on the side of the highway, soaked to my core, less than 10% done with the day’s mileage and moving at half my normal pace, and started laughing. What was I even doing here, in a corner of Japan so remote they don’t even run train lines to it, hugging the gutter of a flooding highway in failing rain gear? I’m on sabbatical and could be anywhere on earth, and I’m here, doing this?

With the tension momentarily broken, the situation became easier to assess. I was soaked, but not cold. I was moving slowly, but still moving. The road demanded more attention, but it was rideable. The terms of the day became simple: slow down, ride defensively, keep the bike upright, and make steady progress north.

As my mood turned for the better, I began noticing how Kyushu changes in the rain. The foliage deepens in color, mist settles in the valleys, runoff gathers into waterfalls high on the coastal cliffs, reflections scatter as droplets break up the surface of flooded rice paddies. Shrines and temples take on a different feeling: darker stone, brighter moss, wet steps, fewer people, the whole place quieter and older-feeling than it had been under clear skies. I was still soaked, still moving far slower than planned, and still listening nervously to the grit in my drivetrain, but I was beginning to appreciate this different side of the island rather than solely focusing on surviving the day.

By the time I reached my hotel, my shoes were full of water and every piece of clothing I had on needed to be wrung out over the bathtub. Nothing about riding in the rain had become fun, exactly. But it was no longer a disaster waiting to happen. It was just weather.

Tempo

In the imagined version of this trip, the day ends soon after reaching the lobby of my hotel for the night. Check in, shower, eat dinner, sleep. In practice, arriving is the start of a second shift. First I have to find out where the bike is allowed to sleep. Then I partially disassemble my rig in the parking lot, pull the bags off the bike, unfold my packable duffels, and convert the whole contraption from “vehicle” into “luggage.” Only then do I walk into the hotel, trying to look less like a spandex-laden swamp creature than I actually am.

Once inside the room, the hotel becomes a tiny operations center. Wet clothes need to be washed or hung somewhere they might plausibly dry by morning. Electronics need to be triaged according to the limited number of outlets, cables, and adapters I have on hand: phone, bike computer, lights, cameras, headphones, laptop, battery banks. Footage has to come off SD cards, onto hard drives, and sometimes into the cloud, assuming the hotel WiFi is feeling generous. Loved ones need updates. Strava needs an upload. Dinner still has to be found. And under all of this is the quiet knowledge that tomorrow is not fully planned just because a route exists on my cycling computer.

That was probably the biggest logistical surprise of the trip. I had spent months designing all 49 cycling days in advance, but none of those routes could simply be pulled off the shelf and ridden without adjustment. Weather changes, hotels sell out, ferries run on specific schedules. A route that looked sensible on a laptop sometimes needed adjustment once I knew more about the traffic, tunnels, climbs, food gaps, or advice from locals. Some nights this meant a quick check and an early bedtime. Other nights it meant an hour of comparing translated hotel pages, scanning road reports, checking cancellation windows, and deciding whether to push farther tomorrow because a storm was coming the day after.

Morning weather check, ride, arrive, unpack, wash, charge, eat, route-adjustments, final weather check, sleep. Every few days, book the next block of hotels. Every week, zoom out and audit the next few hundred miles. The climbs, the hot springs, the meals, the beautiful stretches of coast road — all of them depend on this machinery working in the background.

Departing the Coast

When planning my route through Kyushu, the most significant design choice was whether to keep following the eastern coastline north or turn inland through the mountainous interior. The tradeoff was simple: the coast would be flatter, faster, and more predictable; the interior would mean more climbing, more weather exposure, and more uncertainty, but it would also take me through many of Kyushu’s most dramatic landscapes.

After five days of coastal riding, I woke in Nobeoka and turned west, putting the ocean behind me and a wall of wet green mountains ahead. The road steepened almost immediately. The broad coastal plains gave way to gorges and suspension bridges, and the occasional coastal tunnel gave way to kilometer-long behemoths slicing through ridge lines. After several days of rain, the mountains seemed to be draining from every surface: water running down cliffs, spilling from culverts, and gathering in streams far below the bridges. Road signs warned of sharp turns, monkeys, and boar crossings. The agricultural towns of the coast gave way to sporadic gas stations and konbini stops along the mountain highway.

Takachiho was the first place in Kyushu where I felt the machinery of tourism fully appear around me. After the biggest climbing day of the trip so far, I arrived at my hotel and was greeted in English by an attendant waiting in the parking lot. At check-in I was handed a town tourism packet and met with confused looks when I explained I hadn’t reserved a spot at the traditional folk dance ceremony at the local Shinto shrine that evening. I was assured I could probably still get one of the last spots if I’d just scan the QR code behind the counter before the next wave of tour buses arrived. After days of business hotels, local restaurants, farm roads, and Google Translate interactions, I had entered a place that knew exactly how visitors moved through it.

The next morning I rode down toward Takachiho Gorge at sunrise and found myself tucked between oversized coach buses on the hairpin switchbacks leading to the parking lot. This could have felt deflating, except the gorge is famous for a reason. It is an astonishing piece of geology: a narrow river channel cut through ancient lava flows, with sheer basalt walls rising on both sides, waterfalls spilling from the cliffs, and dense vegetation leaning over the rim. In the early light, reflections from the river moved across the angular basalt columns while bright, toy-like rowboats drifted through the green water below. I walked the paved path along the cliff’s edge and joined the rest of the crowd waiting at the marked overlooks for the same photographs everyone else was taking.

After an hour wandering the gorge, I bought an 8:30am matcha ice cream from the rest stop, packed up my bike, and set my GPS to continue inland. Getting out of town required grinding back up the same switchbacks I had descended that morning, pulling into turnouts every few hundred feet to let buses and rental cars pass.

Hot Springs

One of my core design principles for the route was simple: thread the onsens.

Long-distance cycling prepares the body for a bath with incredible efficiency. Sweat, sunscreen, road grit, chain grease, and the occasional dusting of volcanic ash accumulate until you feel like a grimy shell of a person. Hours hunched over the handlebars tighten the back and shoulders; hours of climbing and headwinds work the same muscle groups until even sitting still comes with a full inventory of aches. At the end of a day like that, the hierarchy of needs becomes very simple: scrub off the road, get warm, sink into hot water, and let the body report back on what still works.

My first real encounter with Kyushu’s hot springs came in Oita prefecture, on the north side of the island. I had booked two nights at a small ryokan tucked high on a forested ridge outside Oguni, and after check-in an attendant led me to my room. At the far end, she slid open the doors to reveal something I had somehow overlooked in the booking description: a private hot spring built into the rocky landscape just outside my room, tucked partly under an awning, shaded by Japanese maples, and fed by a continuous flow of natural spring water from somewhere deep below the ryokan.

After a thorough scrub in the outdoor shower, I lowered myself into the almost-too-hot water and felt the heat move through my legs, hips, and lower back. Rain pattered just beyond the awning. Fresh spring water burbled continuously into the tub. Frogs called from somewhere in the darkening forest. With my chin just above the surface, I leaned into a deep hamstring stretch and reminded myself to drink enough water to avoid dehydrating while literally submerged in a tub. I stayed there until 3am that first night, reading essays on my Kindle, pruning my fingers, and coming to terms with the uncanny feeling of getting more or less exactly what I had hoped for.

Two days later, I reluctantly left the ryokan and rode north toward the coast. As I moved through Oita prefecture, it seemed as if every storm drain, roadside gutter, and forest creek was venting steam into the atmosphere. Pieces of public infrastructure belched white clouds from pressure-release valves, tapping hot spring sources deep underground and distributing the water to onsens and ryokans in the area. Towns advertised day-use baths with steam-powered wooden water wheels facing the street. Public parks offered spring-fed foot baths to passing tourists. The whole region seemed to be leaking heat.

Descending out of the coastal range toward Beppu, the air itself took on a faint sulfur smell, one I had already come to associate with relief. As I dropped below the fog layer, the city spread out across the coast below me, with dozens of steam plumes rising from hotels, bathhouses, vents, and pipes. In Oita, hot springs did not feel separate from the terrain I had been riding through all day. The same volcanic landscape that made Kyushu steep and unstable also produced the water I was using each night to recover from crossing it.

Northward

Writing something like this is interesting because I'm trying to capture aspects of the trip after they've had enough time to form into beats but before the nuances and rough edges have worn away with distance and fading memory. I'm publishing this from Osaka, nearly a month into my journey, and much has changed since leaving Kyushu. I'm more comfortable on the bike, less awkward in my daily interactions with locals, and have settled into the tempo of a ravenous spandex-clad creature whose daily highlight is the look on people's faces when I tell them, in Japanese, where I started and where I'm going.

I'm hoping to get more of these out, but writing is a slow process for me and I'm trying to make sure that processing the trip doesn't end up supplanting the experience of actually living it. That said, the second island of Shikoku was incredible and I'd love to share some thoughts on cycling through its rugged interior. If you're interested in daily updates, you can find little blurbs and photos on Strava, which is the only social media I'm actually updating for this trip.

Subscribe now

AI Disclosure — Claude gave some editing feedback and generally reigned in my rambling

Last year I stumbled upon Oscar Boyd’s documentary of his cycling traverse of Japan and immediately knew it was a trek that I had to attempt myself. It not only entails the type of grand physical challenge I’m naturally drawn to, but also offers a slower, more grounded way of moving through a country I had long wanted to see. After deciding to embark on my cycling journey across Japan, I ran into an obvious question — which route across this country should I take?

I began researching and came across a number of cycling routes connecting the southern and northern tips of the main Japanese islands, including the one Oscar Boyd himself followed. While these routes helped give me an idea for what a trek like this would entail, none of them seemed like the right one for my trip. These routes were following the contours of the landscape more efficiently than I thought was ideal, diverting around scenic areas I was interested in visiting and taking direct paths where I thought it might be valuable to wander. Seeing this, I began to consider what it might mean to design my own route from scratch.

While this task seemed daunting, as I sat with it, it became clear that designing my own route would provide two major benefits. The first is that it would allow me to construct a route customized to my specific circumstances and desires. Second, and importantly, it would give me an opportunity to spend a few months studying the landscape, infrastructure, and culture of Japan, acquainting me with this place long before I stepped off the plane in Tokyo with my bike in tow. These benefits convinced me to take on the task of designing my own path across this country.

This post is an overview of my route, which I’m calling The Scenic Route. It’ll walk through the high-level design principles behind the route, spend a bit of time detailing the actual process I used to construct 3,700 km of GPS tracks across the country, and will show some of the fine-grained texture of the route by examining a handful of notable design choices I made along the way.

Subscribe now

Quick Resources

• Introductory Post: The Scenic Route

• GPX Files: RideWithGPS Collection

• Route Viewer: Google Maps Rendering

Route Philosophy

While reviewing the existing routes online, I noticed they were designed with a fundamental constraint — completing the traverse in around 30 days of cycling. This demanded a level of efficiency and pacing, over 100km per day of cycling, which explained why they skipped some of the detours I was interested in taking. Given that I’m on sabbatical for all of 2026, I had a much more time and flexibility than the normal traverse cyclists.

This realization led me to the overarching philosophy for this route:

you have the rare luxury of time, don’t waste it.

While this philosophy provided a north star, it wasn’t concrete enough to guide me through the thousands of large and small decisions I would need to make while actually building the route. This philosophy alone doesn’t tell me which small towns are worth diverting into the mountains for, or whether it’s worth an extra 2,000 feet of climbing to get off an efficient highway and onto a remote forest road. I needed more than just an abstract philosophy, I needed a practical set of design principles to help me through the route construction process. After iteration and fine tuning, these are the design principles I ended up with:

1. Nature over infrastructure: Epic coastlines, deep forests, and towering mountain passes over cities and highways. I’ll have opportunities to see Japan’s wonderful cities on other trips — this trek is mostly for the places inbetween.

2. Find the best backroads: While modern highways are the most direct and efficient, Japan contains a long tail of well-maintained backroads that go deeper into the scenery and further away from traffic.

3. Thread the onsens: I’m a sauna and hot spring enthusiast, and Japan is the motherlode of natural hot springs. Routing through the onsens is more than just a luxury, it’s a chance to build active recovery into the itinerary.

4. Go where I won’t go back: Getting to Tokyo again is easy. Getting to the spine of Shikoku, the Sea of Japan coast, or rural Hokkaido might never happen again.

5. Leave room for serendipity: A regret I have from previous travels is packing my schedule so tight that I couldn’t chase the unexpected. I’m baking in frequent rest days on this trip, which not only provides a buffer against extreme weather or acute injury, but also to enable me to dive deep into niche aspects of Japan’s landscape and culture that I couldn’t have anticipated.

Applying these principles repeatedly over months of planning pulled the route toward all sorts of interesting and unexpected corners of Japan. To show how those principles worked in practice, I’ve picked out a handful of design choices to examine in more detail.

A Few Defining Choices

A 3,700km cycling route is made up of hundreds of different decisions, large and small. Rather than trying to catalogue them all, I selected four significant decisions I needed to make along the trip and will examine how the design principles helped me navigate the tradeoffs involved. I’ll dive into one decision from each of the four islands this route passes through, to show how the principles play out across different terrains and under changing sets of constraints.

Kyushu — Through the Aso Caldera

Kyushu is Japan’s southernmost main island and contains the starting point for all south-to-north traversals of the country: Cape Sata. Most routes start at this southern tip and head northwest, hugging population centers like Nagasaki and avoiding the mountainous interior for as long as possible before cutting across the island at the narrowest point and exiting Kyushu by ferry on the eastern coast.

The Scenic Route takes a different path entirely.

The route starts by heading up the rugged and sparsely populated eastern coast of the island. It slogs along the coastline for four days before hitting the first major decision point — stay on the coast or head inland?

The tradeoff was clear. I could continue hugging the coast until turning the northwest corner of the island and ending up at the city of Oita, where I would catch a ferry and continue on with my route. This would not only minimize mileage and elevation gain, a tempting prospect for the first week in the saddle, but would also place me into some of the most remote, tropical coastline in the country. On the other hand, heading uphill through the coastal range would place me on an intersecting course with a handful of Kyushu’s most famous and scenic areas — onsens, volcanic ranges, tropical mountain canyons, and more.

I decided to head inland.

Once off the coast, I would cross the massive coastal mountain range and enter the volcanic flatlands of the interior, specifically the area around the Aso Caldera. While it’s much easier on the legs to simply pass around the outer rim of the caldera, the otherworldly scenery through the center seemed well worth the extra effort. This area is famous among cyclists on the island, and one look at the roads makes it clear why this is the case.

Once across the volcano and on the north side of the caldera, I need to get to the port city of Oita to catch a ferry to the next island. Direct routes all follow a series of highways that quickly descend out of the mountains through busy corridors and dump out at the major cities along the coast. The highways looked fine for cycling, but I did some exploring and found a handful of alternate roads that hug the contours of the lush Kyushu mountains.

I ended up stringing together a sequence of these older and almost abandoned-looking backroads that would take me to the town of Kurokawa Onsen. Some of these roads look as if they haven’t had any vehicle traffic in years, and often have gaps of dozens of miles between services. It’s a bit of a risk to divert this far away from civilization, but the scenery and solitude seem too good to pass up.

Kurokawa Onsen is a charming small town, home to a collection of rustic and family-owned onsens. I decided to take one of my first rest days for the trip in this town — an opportunity to relax in a cozy and relatively secluded corner of Japan that should stand in contrast to the busier and more modernized onsen towns I will frequent later in my trip.

After my rest day I’m left with a 6,000-foot descent to the coast across 45 miles of winding mountain roads (route link), dumping me out at the onsen city of Beppu and perfectly staged to hop across Beppu Bay to Shikoku to continue my long journey north.

Shikoku — Along the Rugged Spine

While Shikoku is Japan’s least visited major island, it has become known for cycling in recent years. Much of that fame comes from the famous Shimanami Kaido, a protected cycling route that hops across a chain of islands connecting Shikoku to the main island of Honshu through Setonaikai National Park. It’s not uncommon for cyclists to travel internationally to Japan just to ride the Shimanami Kaido.

The Scenic Route avoids this area entirely.

The Shimanami Kaido is supposed to be one of the most pleasant cycling routes in Japan. But taking it would have meant leaving Shikoku almost immediately, exiting the island only a day after entering from the west. That felt less like traversing Shikoku than skimming its edge. I wanted to see the island in its own right, which meant turning away from the populated northern coastline and looking instead toward the mountain spine that runs through its interior.

That search eventually led me to the UFO Line, an exposed ridgeline road better known among motorcyclists than cyclists. Getting there required a full commitment to the island’s underexplored interior, trading the relative certainty of the coast for one of the least documented sections of the entire trip. It was a big commitment in every sense: remote, sparse on services, and large enough to force my longest day of the whole route, at 78 miles and over 10,000 feet of climbing (GPX link).

Reaching the UFO Line requires leaving the coast at Matsuyama and climbing roughly 4,000 feet into the small town of Kumakogen, the only nearby place with reliable lodging. From there, the ridge traverse itself has sparse and inconsistent resupply, some of which may not even be open that early in the season. And even after the main event is over, I still have another 40 miles and 4,000 feet of descending to cover before reaching the next town with lodging, Motoyama.

Shikoku is full of well-known cycling routes, but most of them hug the northern coastline where the major towns and cities are. The deeper I looked into the island’s interior, the less information I could find about road quality, cycling traffic, and workable itineraries between lodging and resupply points. That uncertainty made this section genuinely hard to design. I’m still a bit nervous about it: 14,000 feet of climbing over two back-to-back days with sparse resupply would be a demanding sequence even in familiar riding territory.

In the end, the well-trodden coastal routes just didn’t seem to align with the principles shaping this trip. At the same time, Shikoku’s interior was one of the least documented parts of the entire route, which made venturing into it feel both risky and worthwhile. I’m hoping not only that this turns into one of the most memorable stretches of the ride, but that my own notes and photos can make it easier for future riders to head in the same direction.

Honshu — Off the Bike For Golden Week

Honshu is Japan’s largest island and is the one with the greatest number of potential cycling highlights: the temple-filled Kii peninsula, the Japanese alps, and the northern coastline along the remote Sea of Japan. There’s more to say about this island than anywhere else on my route.

Despite all of that, the most important decision I made when planning Honshu was staying off the bike for an entire week.

Japan has this cluster of holidays called Golden Week, when four national holidays align close together around the beginning of May. Many people stretch these holidays into a full week off, making it one of the peaks of domestic travel. In practice, this means that people depart the cities and head for precisely the remote and scenic corners of Japan I’d otherwise be cycling through.

The start of Golden Week will coincide with my 3rd week on the bike, and I expect to be sore and in need of some extended recovery by this point. I decided to take this opportunity to head into the cities while the rest of Japan is leaving them to head for the countryside. Specifically, I’ll be taking the entire week off of the bike to make a home base at a nice hotel in the city of Osaka. From my home base, I’ll explore Osaka (affectionately known as the “Kitchen of Japan”) on foot and perform any major cycling kit upgrades that announced themselves as obvious during the previous few weeks of travel.

I’ll also use this opportunity to spend 2 days in Kyoto, a city which is often called the cultural and historical heart of Japan. Kyoto itself should be crowded during Golden Week, but I figured that if I was going to absorb the brunt of the travel rush anywhere, it’s better to do it on foot while in one of the world’s great cities than from the saddle on crowded forest roads.

It may seem strange to give so much weight to a week spent off the bike, but this was one of the most important route decisions I made. Six days of rest gives me time not only to recover physically, but to adjust my kit after the first 800 miles, fix any obvious problems before the Alps, and let the trip breathe a little before I head into some of the best riding in Japan. It was difficult to assign myself a long break right as the route starts getting especially good, but I suspect my future self will be grateful for it.

Hokkaido — Turned Back From the Depths

Since deciding to design my own route across Japan, the section I was most excited about planning was the island of Hokkaido. It appeared different from the other islands in ways that encouraged exploration — it was huge, sparsely populated, criss-crossed by large mountain ranges, and full of national parks and wilderness areas. Bikepacking forums highlighted vast networks of roads through the mountainous interiors and along the coasts, and a quick glance at satellite imagery showed a green expanse begging to be explored. Above all others, this island seemed like the one which would most strongly reward deep research and bold route planning.

While researching, I found two popular routes across the central part of the island. The first route starts in Sapporo and follows the path of least resistance, staying between parallel mountain ranges and hugging the valley floor as it weaves through sequences of farming towns and small cities all the way to the north tip of the island. The second route, and the one taken by Oscar Boyd, heads from Sapporo to the west coast and hugs the rugged coastline all the way to the northern cape. These two common routes are shown below.

Neither of these routes felt ideal to me. Staying along the valley provides the path of least resistance, but it does this by hugging the most populated corridor of the entire island and avoiding any of the surrounding mountainous areas or national parks. The coastal route ventures through remote and scenic areas, but the highway it follows goes through a large number of long tunnels and can reportedly be very uncomfortable to traverse depending on the traffic.

I set out to build a route which could outdo both of these defaults, but Hokkaido showed it was much more difficult to tame than I had anticipated.

I tried to route eastward into Hokkaido’s remote interior, hoping to reach into the core of Daisetsuzan National Park or through the volcanic ranges that make up the spine of the island. Each attempt ran into the same issue — services thinned out dramatically. 70 mile stretches without the opportunity to purchase food. 100+ mile stretches without lodging. The sparsity of services was unlike anything I had run up against on other islands of Japan. Without camping, this lack of services was more than just an inconvenience, it made it non-viable to venture this far into the depths of Hokkaido.

I scaled back my ambitions a bit and began looking for new routing options. Eager to leave the major population corridor, I charted a route east and which would cross the wide mountain range separating Sapporo from the next valley over. This put me into the center of the famous agricultural region around the towns of Furano and Biei, an area popular with cyclists for the quiet, rolling backroads and with tourists more generally for the picturesque flower farms. From here I found a series of steep mountain roads that climb high up onto the western slopes of Daisetsuzan National Park. This placed me right into the major volcanic region I was so eager to see, added quite a bit of climbing on beloved mountain roads, and allowed me to explore some of Hokkaido’s most famous mountain onsens and wild hot springs. After two days spent high in the mountains, I would slowly drop away from the volcanic peaks and back to the agricultural heart of Hokkaido, where I would converge back with the standard routes across the island.

It wasn’t the most ambitious version of Hokkaido I had imagined, but it felt like the right compromise. One hard day got me out of the island’s most populated corridor and into the agricultural heart around Furano and Biei. From there I could still climb into the western edge of Daisetsuzan, reach the volcanic mountains and their onsens, and keep moving north without forcing the route into something far riskier than this trip could reasonably support.

Despite my grand ambitions, Hokkaido is where the design principles of my route ran into their practical limitations. Avoiding camping had been an easy decision to follow thus far, but Hokkaido showed that there are some areas of Japan that don’t lend themselves to this type of bike touring. The sparsity of services here actually made me appreciate the relative ease with which I was able to plan the first three islands of this trip. While I’m mostly happy with how my route here ended up, I still feel the draw to further explore the more remote corners of this island. Some places are better saved for a future, different kind of trip.

From Idea to Itinerary

Actually sitting down and constructing this route from scratch presented a daunting problem. I knew basically nothing about Japan when I started — seasonality, geography, culture, etc, all of it was foreign to me. The problem seemed so large and amorphous that it wasn’t even clear where to begin.

A bit overwhelmed by the scope of the problem, I went out in search of constraints which could narrow the decision space. The first useful constraint I found was seasonality. There are really only two viable windows for a full bike traverse of Japan: spring if you want to head north and stay ahead of the monsoon rains, or early autumn if you want to head south before snowfall returns to the mountains. Since I wanted to ride north, my window was roughly early April through June.

The next step was to begin familiarizing myself with the geography of the country. I started simply by meandering through Google Maps, but Japan is simply too large to take in by clicking around a digital map without any high-level strategy. At this point I actually went online and purchased 2 different physical maps of the country and hung them on the wall of my office, and committed to spending 15-20 minutes a day for a few weeks looking over them.

This helped me begin to soak in the major features — islands, cities, bays, mountain ranges, etc, and motivated me to research specific parts of the landscape by looking up travel videos on specific islands and cycling videos through specific areas. Slowly, over the course of a few weeks, I built up a coarse mental model of the landscape and felt like I was making minor conceptual progress on the problem.

The coarse mental model gave me the confidence to dive into the deep end and begin planning the actual route itself, island by island, starting with Kyushu.

Zooming into a specific island, I applied the same pattern from before — search for constraints to narrow the scope of the problem. Here is where the landscape made itself useful. For example, Kyushu presents the options of cycling up the east coast, the west coast, or straight through the center. The west coast means spending time cycling through major cities, and so was eliminated as a direction of travel. Heading through the central mountains seemed appealing, but going against the grain of the island slowed my northward momentum too much. The east coast avoided major cities, was relatively rural, but allowed for steadier northward progress, and so that was the direction I decided to take my route.

This was the general pattern. Pick a specific zoom level, like that of an island, a region, a mountain range, or a single coastal road. Begin looking for natural constraints imposed by the environment — service gaps, long tunnels, major highways lacking good alternatives, etc. Integrate these constraints and begin eliminating possible routes. When you think you’ve satisfied the constraints at one level, zoom in, and repeat the process. Often what seems like a good plan from one level of granularity runs into issues once zoomed in, which requires backing out, revisiting earlier decisions, and trying again with a better understanding of the landscape.

After a few of these iterations, I ended up converging on a tooling stack that would carry me through the next few months of the route design process. I used RideWithGPS for laying the actual “tracks” of the route, GPS point by GPS point. Cycling heatmaps helped me figure out which roads and corridors were popular with cyclists. Google Streetview allowed me to get a detailed sense of what it was actually like on the road — bike lanes, asphalt quality, traffic levels, etc. Finally, ChatGPT served as a general research partner, particularly helpful for finding Japanese-language content like cycling blogs and government tourism websites.

To give a quick sense for how this tooling stack works, I’ll examine a consequential section of the route on Shikoku and show how the tools helped guide me through some tough decisions.

My biggest day on the entire route comes on Shikoku, where I plan to traverse the UFO Line along the spine of the island’s mountains. It’s roughly 80 miles with more than 10,000 feet of climbing, so I wanted to stage as close to the start of the ride as possible and arrive there with fresh legs. The problem is that this part of Shikoku is sparse on services, leaving me with only one realistic staging point: the small mountain town of Kumakogen. Reaching it means leaving the coastal city of Matsuyama and climbing up into the interior.

When I first laid out this day, I followed the obvious route: Highway 440 straight out of Matsuyama to Kumakogen (route details here). It made for a relatively easy stage by the standards of the trip, covering about 21 miles with only 2,000 feet of climbing. That was appealing. It would keep my legs fresh, give me plenty of time to settle into Kumakogen, and set me up well for the much harder day to follow. It was also the route Google recommended between the two towns, and the heatmaps showed that cyclists used it regularly.

I came back a few days later while reviewing my sequence through Shikoku and decided to take a closer look at this specific section. I looked at Street View for highway 440 and noticed that while it definitely was cyclable, it didn’t look like the type of road I’d want to hug the shoulder on for 20+ miles while trudging uphill.

On top of that, I noticed that the heatmap contained an interesting winding offshoot a bit further north along a small road that seemed to disappear into the forest before faintly picking back up again on a ridge about Kumakogen (see the road heading south from Toon in the heatmap image above).

I zoomed in on the heatmap and found this road, Prefectural Route 209 which starts off looking similar to Route 440 near Toon but quickly turns into this.

A narrow one-lane road that meanders its way through the depths of Shikoku’s forested mountains, passing by the occasional shrine and waterfall but otherwise avoiding towns or other population centers. I did some research and found a few mentions of this road from motorcycling groups, but little else. I scanned along its length using streetview and couldn’t find any traffic in the narrow parts, which combined with the lack of towns along its length, suggests that it’s an old forest road which has been rarely used since the parallel highways were constructed.

I began laying down GPS points and ended up with an alternate route (route details here). This route was 50% longer and required 50% more climbing, but seemed like a much more pleasant and interesting alternative compared to my original trek. While still a relatively moderate day by the standards of this trip, I wasn’t sure if it was the best idea to add complexity and difficulty before my long day over the UFO Line.

Instead of deciding which route to keep now, I decided to keep both routes available. This will allow me to decide during the trip which route to take based on how I’m feeling and how the elements are treating me. This felt like a reasonable compromise. I could keep the shorter route as my default so I wouldn’t exhaust myself before the UFO Line, but leave the more adventurous option open in case I felt up for it.

Building alternate routes between Matsuyama and Kumakogen is one small example of this process at work. Repeated across dozens of decisions at different scales, it’s how the route slowly took shape. What began as an unfamiliar country gradually became legible, and as my understanding of Japan deepened, planning each day became less daunting and more enjoyable. The result was more than a line on a map: it was a route that began to feel coherent across days, islands, and the country as a whole.

Time to Ride

The Scenic Route is my honest attempt at constructing a trek that allows me to experience Japan at human scale and according to a particular set of preferences and a particular point of view. Going through this process did more than just leave me with a bespoke line across Japan, it allowed me to begin acquainting myself with this country long before I left the comfort and familiarity of my cycling home in San Francisco.

My hope is that this post explained why I decided to undertake this task of designing a route from scratch, and that it provided some insight into what the process of constructing a route of this size and complexity actually looks like in practice. Despite this post’s length, there is a lot of route and process detail that I wasn’t able to go over. If you have any questions about the trip — my tooling stack, conducting research, the actual process of laying down GPS marks — feel free to ask in the comments and I’ll do my best to answer. I expect to have much more to say about this route in the near future once I’ve stepped away from the computer and experienced it up close.

With that said, the route has been finalized, and while it’s not perfect, I’m quite happy with it. The only thing left to do is get out there and ride the damn thing.

It’s 2am on a Sunday night and I find myself sitting at my desk with a hundred familiar tabs open and a growing collection of empty hop water cans scattered in front of me. I zoom in on a view of Hokkaido’s northern coastline and click to set a new GPS marker, extending a line across the map to this latest point of interest. I click the “export” button, download japan_cycling_route_day_49_final.gpx, and finally close out the giant tab group which has occupied space in my browser for many months now.

I’m biking across Japan.

All of Japan, from the southern tip to the northern tip, and I’m calling it “The Scenic Route”. It’s an honest attempt to see Japan at bike speed: epic coastlines, dense forests, tall mountains, rural villages, incredible hot springs, and the small places you don’t reach on a normal trip.

Getting here was exhausting, and I haven’t even begun cycling yet. Months of meticulous research, dozens of hours spent inspecting maps, and thousands of hand-placed GPS waypoints. But my planning is finalized — my flights are booked, my new cycling gear has been purchased, and my resignation has been handed over to HR. My contiguous route across the entire length of Japan is now set.

It was easy to keep adding miles and mountain passes from the comfort of my desk. Now I have to go out and ride the damn thing.

Subscribe now

Details

• Starting point: Cape Sata on April 12th

• Ending point: Cape Soya on June 10th

• Timing: 8 weeks on the bike (including rest days and side-quests)

• Distance: 2,300+ miles (3700km)

• Elevation: 130,000+ feet (43,500m)

• Map Viewer: Google Maps Rendering

• GPS files: RideWithGPS Collection

The “Scenic” Route

Japan is one of the world’s best cycling destinations, and there are an uncountable number of different ways to traverse it by bike. While I researched a number of existing routes, I ultimately decided that I’d regret passing up the opportunity to design my own route from scratch. This is my chance to chart my own path across the country, a path that allows me to interact with Japan according to my own travel philosophy. Simply put, I’m optimizing for beauty and experience over efficiency.

Here are my guiding principles:

1. Nature over infrastructure: Epic coastlines, deep forests, and towering mountain passes over cities and highways.

2. Find the best backroads: While modern highways are the most direct and efficient, Japan contains a long tail of well-maintained backroads that go deeper into the scenery and further away from traffic.

3. Thread the onsens: I’m a lifelong bathing enthusiast, and Japan is the motherlode of natural hot springs.

4. Go where I won’t go back: Getting to Tokyo or Osaka again is easy. Getting to the spine of Shikoku, the Sea of Japan coast, or rural Hokkaido might never happen again.

5. Leave room for serendipity: A regret I have from previous travels is packing my schedule so tight that I couldn’t chase the unexpected. I’m baking in frequent rest days on this trip — not only to provide a buffer against extreme weather or acute injury, but also to enable deep dives into niche aspects of Japan I couldn’t have anticipated.

Why This and Why Now?

After 10+ years in industry and 3 incredible but exhausting years at OpenAI, I quit my job in early 2026. I’m taking a year-long sabbatical, not just to step back from work, but in order to do something epic. I’m trying to make the most of a window of opportunity to deeply explore other cultures and natural environments before my circumstances and priorities change (kids…).

At this point you might be asking reasonable questions, like:

John, have you ever done an overnight bike trip?

Do you read kana or speak any Japanese?

Wait, have you ever even been to Japan before??

You may be surprised to learn that the answer to all three of those questions is: “no”.

And, that’s part of the point. Years spent behind a computer screen as a productive software engineer have me yearning to do something extremely intense, a bit crazy, and far outside of my comfort zone. Sure, I could do a classic Tokyo trip, but it wouldn’t scratch the itch I’m feeling for adventure. I could even do a long cycling trip across a country I’m already familiar with, but that still wouldn’t match what I want out of this sabbatical. I’m in dire need of getting my ass kicked, and nothing less than a full traversal of Japan under my own muscle power seemed capable of satisfying my ambitions.

At the same time, I’ve been a dedicated wilderness backpacker for much of my life and have collectively spent months of my life exploring wilderness areas by foot. I’m used to doing difficult physical things in extreme environments for extended periods of time. While the actual cycling of this trip will be hard, the incredible food, comfortable ryokan lodging, world-class infrastructure, and friendly locals should make this trip rewarding and genuinely enjoyable. It will be tough, but I know I’m up for this challenge.

Documenting the Journey

Part of this trip is the doing. The other part is the documenting. Before I leave, I’ll be writing about the route-building process, gear decisions, and the design philosophy behind the trip. On the road, I’ll post shorter dispatches when the mood strikes: notes on a brutal climb, a perfect onsen, or whatever I’m thinking about while sprawled on the floor of a ryokan waiting for my legs to forgive me. After the trip, expect longer trip reports, photo essays, and reflections on what it’s actually like to bike across a country you’ve never been to. I’m also bringing a camera and some video gear, so there may be a simple long-form video eventually… but the writing is the main thing.

Follow Along

I feel incredibly lucky to have a window in life where I can try something this absurd, and I’m grateful to the people who’ve nudged me toward doing it instead of just daydreaming about it. Wish me luck. I’m sure I’ll need it.

John