Just one boat ride from Takeshiba Station, located right next to Hamamatsucho in the heart of the city, and you can start your bicycle trip instantly upon arrival and disembarkation! Izu Oshima is a perfect destination for a weekend ride if you make full use of Friday night's overnight stay on the boat and Saturday and Sunday. The island itself is a modest 50km in circumference, but the course is hilly and challenging. However, Tsucchi and I have conquered a lot of the steep hills in the past, so I affirmed, "Well, we've got plenty of time to finish!" We thought that we would be able to enjoy the ride without any problems, but we had a big mechanical problem right at the beginning of the ride, so it turned out to be a crazy trip.

Kenta-san's Travel Bookmarks

22:00 Departure from Takeshiba Passenger Boat Terminal, Tokyo

DAY 0 is over!

6:00 Arrival at Okata Port
7:30 Ride Start
8:30 Breakfast at "Taisho" in Motomachi Port
10:00 A short break at the "stratified rock formation"
11:00 Arrival at Habu Port
11:10 Croquettes at Ukai Shoten
11:20 Lunch at HAV Cafe
14:15 Ura-Sabaku (Ura Desert) at Mt. Mihara
15:20 Rest at Oshima Park
15:50 Senzu-no Kiridoshi
16:15 Goal at Okata Port / Overnight stay at Funayoshi guest house

DAY 1 is over!

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word of mouth.

Boat & Bicycle trip starting in the middle of the city

Departing from Takeshiba Passenger Boat Terminal!

The trip starts at Takeshiba Passenger Boat Terminal near Hamamatsucho in Tokyo's Minato Ward. We arrived two hours early (8:00 p.m.) to allow plenty of time to catch the 10:00 p.m. departure of the large ferry. Since we booked a tour with Tokai Kisen this time, we picked up our reserved tickets at the reception desk, filled in our names and addresses, and waited for the ship.

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Boarding the ship at last!

With our bike bags packed, we are off to Izu Oshima!

Boarding begins 15 minutes before departure (21:45). Tokai Kisen's large ferries allow passengers to bring bicycles on board free of charge as long as they are packed in a bike bag (bicycles can be checked in without a bike bag for an additional fee of 1,500 yen). We will board the Sarubia Maru, a large passenger ship with a capacity of approximately 1,300 passengers. The first thing to do is to leave your bicycle in the bike room. The ship is gently rocking, so there seems to be no danger of the bike falling over.

Super spacious 2nd class Japanese style room

Still, I like the corner.

The Sarubia Maru has a range of rooms, from "first class" to "second class," and this time we reserved the most reasonable second class Japanese-style room, which sleeps 12 people in a group sleeping style. Luckily, the Japanese-style room allotted to us that day was empty apart from us, so we had plenty of space. It seems that the rooms are often empty on weekdays. By the way, the air conditioning on board is very strong, so blanket rental (100 yen/blanket) is recommended.

Arrive at Okata Port at 6:00am

My motivation for the ride is strong!

I fell soundly asleep to the gentle bobbing of the boat, and when I woke up, Oshima was just outside my window. I was thrilled to see the relaxing harbor, a far cry from the urban waters from which I had departed yesterday.

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"All right! Oshima round-the-island ride, let's go for it!"

A strange noise, a pedal that suddenly loses its tension, and when you turn around, there it is...

After assembling the bicycle at the port, we started to ride to a nearby guest house, when suddenly, Tsucchi's bicycle made a nasty sound like..." CRACK!". We looked and found that the rear derailleur was broken near the hanger. It must have been a result of the wind that knocked it over when he was assembling the bike at the harbor. Tsucchi stared at the bicycle in disarray in the distance.

Bicycle trips take you on a road trip, and the world is a compassionate place

The savior "Bicycle People" appeared.

The two of us were in trouble and at our wit's end, but from nowhere our saviors appeared. It turned out these folks were on the same ferry as us and were all experienced cyclists, including veterans and bicycle store owners who had been cycling for a long time. They all put their heads and wits together, removed the rear derailleur, shortened the chain with the tools they had on hand, and modified the bike so that it could run without a gearshift. Even though we had to spend precious time dealing with the trouble, the cyclists said, "When times are tough, we should help each other out!" which warmed Tsucchi's heart. Now it looks like we will manage to complete our round trip of Izu Oshima (no, we have to!).

Leave your baggage at the inn "Funayoshi"

Riding empty-handed is the best part of a round trip

We said goodbye to everyone who helped us with gratitude and headed to tonight's inn, Funayoshi. A cyclist-friendly inn with bike racks at the entrance. We left our backpacks and other baggage behind to make ourselves light. Since losing his gears, it was such a relief for Tsucchi to be able to unload it!

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Finally, the first lap around Izu Oshima begins!

Driving counterclockwise on the Oshima round-the-island road

First on the itinerary is to find somewhere for breakfast. We rode about 10km on Prefectural Road 208, a.k.a. "Oshima Round-the-Island Road," to "Motomachi Port. The traffic was light, probably because it was a weekday, and the ride was comfortable. The route this time is basically on this "Oshima round-the-island road.

Recharge the energy we've used in the morning's mad rush!

Teishoku Restaurant "Taisho"

After a leisurely one-hour ride, we arrived at Motomachi Port. Our destination was "Taisho," a set meal restaurant famous among the locals for its large portions. The "Ashitaba Fried Rice" we ordered was so large that it could have served two people! Ashitaba is a vegetable native to Japan that also grows wild on Oshima Island and is famous as an ingredient in green juice.

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Earth made baumkuchen is a powerhouse!

Geologic cut surface

After finishing breakfast, it was a 30-minute drive from Motomachi Port to the "stratified rock formation" which is a very powerful sight. It is one of Oshima's tourist attractions and is nicknamed "baumkuchen" by the locals. Although I had seen pictures of the strata before, I was overwhelmed by the scale of the 30-meter-high, 600-meter-long folded strata as they appeared in front of me. There is a bicycle rack, so after a short break to admire the strata, we headed to our next stop.

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Have a break in a quiet harbor with nostalgic townscape

Handmade Korokke (=croquette) from Ukai Shoten

We went a little off the round-the-island route and rode about 30 minutes, stopping at Habu Minato (Habu Port), located in the southeastern part of the island. One thing I wanted to try here was the handmade Korokke (= croquettes) at Ukai Shoten, one of the word of mouth recommended places. The crispy batter is filled with sweet potatoes. And all this for 70 yen! In summer, people who come to Habu Port by cruiser from the Izu Peninsula buy croquettes in large quantities and eat them on the deck of their cruiser with a glass of champagne in hand. It must be the most elegant way to eat croquettes in the world....

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Lovely cafe used for drama filming.

Hav Cafe

I found a fashionable store near Ukai Shoten and wandered in for lunch. The atmospheric building, which was renovated from an old private house, was used as the setting for the late-night drama "Tokyo Hochi Shokudo". I ordered raisin toast and a cafe latte made with Oshima cow milk. The warmth of the hot latte gently spreads through my cold body. The owner of the cafe has been traveling and writing for nearly 30 years and sells pins collected from around the world in his store. We also bought one each as a memento of their trip. In this age when things can be easily purchased on the Internet, things and things that can only be found in a particular place are a small but precious reminder of that place.

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Start of the mountain route of the second half!

Tsucchi started voluntary training

After leaving Habu Port, which we had enjoyed more than we had expected, we headed to our next destination. The west side of the island, which is the destination from here, has steeper climbs than the east side, where we had been riding so far. Tsucchi, who does not have a gearshift, began his training by chasing me in a heavy gear. The second half of the route includes the "Ura-Desert," which is the only desert marked on maps published by the Geospatial Information Authority of Japan. It is said to be a rare area where the black volcanic rocks of Mt. Mihara, the sacred volcano that rises majestically over the whole of Izu Oshima, cover the surface of the earth. The area has been highly praised for its "breathtaking scenery" and "spectacular views" in people's recommendations, and expectations for the area are high.

Going uphill after an uphill slope

"Moon and Desert Line"

After climbing for about an hour (about 10km), we arrived at the junction of the "Moon and Desert Line." It was a 300m climb all the way up to this point, but it was even more of a climb to reach the Ura Desert.... The Moon and Desert Line is asphalt, so bicycles can be ridden to the parking lot nearby, but a steep slope with a maximum gradient of 16% awaits.

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We've arrived at the tourist point for the second half of the route!

Ura Desert(Back Desert)

After about 30 minutes (4km) of biking up the moon and desert line, we finally arrived at the parking lot of the back desert. We got off our bicycles and walked along a narrow mountain path mixed with lava to the back desert. After about 10 minutes of walking, the pitch-black back-desert appeared below us...or so we thought, but unfortunately, it was covered by clouds and our view was completely white. However, the sun occasionally shone through a break in the clouds, and we could see the black earth spreading out. The desert was not silky sand, but more like black gravel.

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Valuable rest point in the second half of the day

Oshima Park

After leaving the Ura Desert, we will head down the moon and desert line that we climbed up to the Oshima Round-the-Island Road. Once again, we headed for Okata Port, today's finishing point. It began to rain on the way there, so we took a break at Oshima Park, about 20 minutes (8km) away. We warmed up with hot coffee from the store and our second croquette of the day. There seem to be very few stores and vending machines on the west side of Oshima. Don't forget to bring some refreshments!

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A power spot with a mysterious atmosphere

"Senzu-no Kiridoshi"

Turn off the Oshima round-the-island road and go to the Senzu area. We took a side road to the old road to reach the power spot "Izumizu no Kiridari" (cut-through of Izumizu). The thick roots crawling along both sides of the cut seem as if they were grasped by large fingers. Two huge trees stretch straight parallel to each other from there, and it is a mysterious sight as if they were originally one tree that was cut in two. Stepping into the staircase that passes between the two trees, the sound of the surroundings disappears, and you enter a different world. Perhaps the sound is absorbed by the soil on both sides.

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Finish at Okata Port!

Complete the ride with a full day of content

Less than 4km after leaving the Senzu-no Kiridoshi, we returned to Okata Port, where we started this morning. It was a short ride of about 50km, but it was an intense ride with various events, starting with a problem at the beginning, a cafe time at Habu Port, and a hill climb to the back desert.

Check in to today's lodging


We returned to the Funayoshi guest house and checked in again. I was shown into a clean Japanese-style room. Dinner was a plentiful array of grilled fish, sashimi, and other local seafood. We toasted with a bottle of beer and reflected on today's ride.

If you want to enjoy yourself a bit more until just before you leave...

Fishing Challenge at Okata Port

The next day, we rented a fishing rod at Okata Port to try our hand at fishing before the Tokyo-bound boat arrived. Despite having almost no fishing experience, Kenta-san caught a nice "Isuzumi," and was very satisfied with his catch. He also got a fresh souvenir.

Return to Tokyo on a flashy jet boat

The journey takes 2 hours! In no time at all, you will be in Tokyo!

On the way back, we boarded a fancy jet boat departing from Okata Port to Takeshiba Passenger Boat Terminal. Bringing bicycles on the jet boat requires putting them in a bike bag, and there is a fee (1,000 yen each), but the speed of the return trip, which takes only two hours, is wonderful.

Places we stopped this time

Takeshiba Passenger Boat Terminal

Okata Port


Stratigraphically important cross section

Habu Port

Ukai Shoten

Hav Cafe

Moon and Desert Line

Ura-Desert First Observatory

Tsubaki Museum

Senzu-no Kiridoshi

Where we are stayed

Guest House Funayoshi

People we met


Cyclists who were also riding from Tokyo to Izu Oshima by boat. They saved Tsucchi from mechanical trouble.

Naoko Terada, Owner, Hav Cafe

A cafe owner who has been traveling the world for over 30 years while writing. I was so honored to have this encounter, and this lady's outlook and lifestyle was such an inspiration to me.

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Outline of the Izu Oshima 'Round-the-Island Ride' route

The trip starts with boarding at Takeshiba Passenger Boat Terminal and disembarking at Okata Port. The tour finishes at Okata Port after riding around the island on the Oshima Round-the-Island Road anti-clockwise. The west side of the island is relatively flat, but the west side has a steep uphill slope.

Video of this side trip