Tokyo to Osaka by bike

Turning 39 this year and seeing beautiful photos and trip reports from friends woh cycled from Tokyo to Onomichi inspired me to have an adventure of my own. I planned it in October; booking hotels, copying and modifying routes for a shortened Tokyo to Osaka trip. I wanted to pack light, move fast, and spend plenty of time speaking Japanese. Every part of my trip delivered.

The trip

This time around, my trip started at midnight in San Francisco with a restful flight that landed at 430am the next day. I built my bike up in the lounge area while enjoying a breakfast of rice balls and Boss coffee. It took me over an hour to find a way out of the hotel area after shipping my bag to Osaka via a Ta-Q-Bin service. I kept going onto large roads and getting yelled at by airport folks, but eventually, I got onto a pedestrian path and rode to the bike road that wound itself up from Haneda to Shimokitazawa. I had lunch at Nuts Exchange before making a visit to Blue Lug and loading-up on coffee. Check-in was at 2pm, and with a quick shower and a change of clothes, I napped until dinner.

To the mountains

The first few days were filled with final prep, tasty food, and lots of coffee. When I left Tokyo on the morning of the 3rd day, I got off to a little later start than was ideal. The route took me west to the bike path, then up and around through the western suburban area before serious climbing for two hours through the mountains to Lake Yamanakako. I didn’t eat enough in order to make up for lost time, but by hour two of climbing I could feel my body protesting. It got colder, and darker, and by the time I made it to my small lodge I was frozen and exhausted. I got to outdoor grill food and make up my caloric deficit, then bathe and sleep before a flatter second day.

Riding to Kofu was perfect. Most of the ride was short climbs and then a long descent into Kofu after waking up next to Mount Fuji. I had a great locally-caught fried fish meal at a roadside cafe in the mountains, and made it to my hotel relatively early. I ate, watched The Americans, and took a luxurious bath. The next day was set to be harder, as more mountains and a lot of miles awaited me between Kofu and Matsumoto.

This was the day I tore a hole in my bib shorts, and had a motorcycle guy help me tape them up. I ran out of daylight and energy in the cold and around sunset in Okaya. My Fairmean rinko bag made it easy to load up my gear for the train, and I rode from the station in Matsumoto up to the Ryokan on the edge of town I’d somewhat unfortunately booked. The place was nice, but the need to ride 20 minutes into and out of town (with a 70m climb) added a layer of challenge. Later, I got a sewing for my shorts (supplemented by a patch two days later), which made riding a bit less embarrassing.

In Matsumoto, I met an English guy named Paul at a coffee shop in the morning, in what turned into a delightful new friendship. I admired his bike, and we started talking. Lunch with him and his wife followed, then later, beers and a request to join my ride the next day.

We set off the next morning together, making our way out of town and into the mountains between Matsumoto and Nagoya. My original plan took me to Nagiso for a night of “glamping,” but the forecast of snow made me change my plans. We rode through snow, tunnels, Japanese wine country, and gorgeous vistas in 33-35F temperatures with snow all day. It was grim at times, but also amazing. I knew we could stop at any train station on the way, which took the pressure off or our finishing at a certain time. We made it to Kiso Fukushima by sunset, and split off from there with Paul heading home and me riding to Nagoya on an express train.

In retrospect I should’ve just stayed in Nagoya for two days, but instead opted to ride up to Inuyama for a short stay before a horribly wet and cold ride to Nagahama. On paper the day was easy, but strong headwinds and constant heavy rain made things rough. To cap off a challenging day that involved buying fresh, dry socks at a 7-11, I crashed near Lake Biwa while trying to merge onto a bike path with an inexplicably high curb lip. At the moment I fell, I could tell my hand hurt and I’d hit my knee. When I got to my Ryokan, the staff got me to my room quick so I could warm up, and I noticed my right ring finger was swelling bad at the third knuckle. The bruise would get worse over the next few days before slowly lessening by the time I flew home. The fear that I had as I woke up in Nagahama was that I wouldn’t be able to ride, but fortunately I was able to put the pressure on my palms and not that joint, or take my hand off the bars when I hit potholes. To play it safe I only rode to Maibara station, around an hour and a half towards Kyoto.

In Kyoto my main plan was to heal my hand a bit, eat good food, and enjoy a day or so off the bike. In a huge surprise, I ran into an old friend from college at a jazz bar. He was traveling with his girlfriend after a lucrative exit from his old company. We caught up, and ate and drank way too much. When I left Kyoto for Osaka, it was bittersweet, since I knew it’d be my last day on the bike until I returned to the states. The ride was pretty and simple; following the river south and settling in at my hotel after a few hours of riding. I’d made it!

I packed my bike and shipped it back to Tokyo, then enjoyed a few days in Osaka and Tokyo of friends and food. I can’t wait to do another bike trip in Japan.


What worked

  • My bags were great. All of them beside the framebag were from Restrap, and I had around 17L of space. Due to the temperatures I had to bring more gear than I would normally want to, including a wool hat and a puffer jacket. I was only miserable one day due to my feet getting wet, but otherwise things went well.
  • Hand pump + my small compressor: I was lucky enough to not have any flats, but I did need to add pressure to my tires a few times due to normal air leakage. These worked well.

What didn’t

  • Next time I ride in the winter, I’ll bring my actual waterproof shoe covers, as the Ornot sock shoe covers were deeply inadequate.
  • My shorts tore after a few days, likely because I put too much pressure on them while getting into and out of the saddle. It’s an issue I’ve had before on a long bike trip, but it’s definitely annoying. Next time I’ll bring a patch.
  • I probably needed a spare shirt for when my shirt was dirty. I didn’t feel like wearing my jerseys off the bike, so next time I’ll have two shirts and one jersey. I expected it to a be a little warmer but realistically I only needed a thermal jersey.


Bar: 7L

  • Toiletries
  • Gear bag
  • iPad mini
  • Dunfri jacket Rear: 7L
  • Spare clothes
  • Sandals on outside Top: 1.5L
  • Snacks
  • Hat
  • AirPods Pro Frame: 3.5L
  • Tools
  • Spare tube
  • Pump

Spare clothes

  • long sleeve shirt
  • socks
  • bra
  • thermal bib
  • leg warmers
  • pants
  • sandals


Day 1 & 2 Nov 25-27: Mustard hotel Tokyo Shimokita

Day 3 Nov 27: Lake Yamanakako

PICA Yamanakako

Day 4 Nov 28: Kofu

Urban Villa Konaya Hotel

Day 5 & 6 Nov 29: Matsumoto


Day 7 Dec 1: Nagoya

Hotel Nikko Style

Day 8 Dec 2: Inuyama

Hotel Indigo Inuyama Urakuen Garden

Day 9: Nagahama Dec 3

Ryokan Beniayu

Day 10 and 11: Kyoto

Alter Museum Kyoto

Day 12 and 13 Dec 6-8: Osaka

Hotel 88 Shinsaibashi

Day 14 Dec 8-11

All Day Place Shibuya