Four days. Three peninsulas. Four hundred and fifty kilometres.
After last year's Tokyo to Kyoto ride mainly through the mountains and west coast, I hatched a plan was to ride up the east coast from Shimoda to Tsukuba hitting 3 peninsulas...
There would be beautiful roads, old friends, good food—and 2 easy active recovery days...theoretically...
Tuesday | Day 1: Izu to Shonan
Wheels were on the ground at 7:30 AM from Ohama, Shimoda. We were feeling crisp, genki, and optimistic, convinced that pedaling hard for the first two hours would help us outrun the incoming rain.
By 9:30 AM, Makita-san and I had knocked out 50k without a drop, earning ourselves a well-deserved second breakfast. The drizzle started just as we polished off our beef bowls, but we pushed on to beat the heavy stuff. Unfortunately, just north of Ito, the skies opened up and clobbered us with a torrential downpour, forcing us to take shelter at Usami—a hidden gem of a surf beach where we pondered why so many surfers were out on a rainy Tuesday morning.
Once the rain subsided 15 minutes later, we rolled out toward Atami, arriving around lunchtime drenched, freezing, and starved until a steaming bowl of ramen brought us back to life. Meeting up with Alan in Manazuru was a highlight, as he gave us the local guide treatment through the back roads down into Odawara for coffee. After Alan peeled off, we tackled the flats of Shonan for the final 30k push to Chigasaki. Highway 1 was a gridlocked nightmare of stop-and-go traffic, but it was a small price to pay to transition between coastal country roads.
Arriving at the hotel felt incredible, even if the stats looked tame on paper: 131k total distance, 5:41 in the saddle, 115 average watts, and 1,284 meters of climbing. The brutal weather had taken a heavy toll, leaving my entire body aching. I fell asleep naively convincing myself that tomorrow was going to be an easy recovery day.
Wednesday | Day 2: Shonan to Tateyama via Bike/Ferry
Day 2 was supposed to be a relaxed, active recovery day featuring a gentle ferry ride across Tokyo Bay to Chiba. The weather gods had other plans, unleashing a harsh storm the moment we stepped onto the boat in Kurihama. We picked our way through Kamakura and Hayama under an intermittent drizzle; battling Shonan’s morning commuter traffic in the rain was hardly the romantic highlight of the tour, but you have to soldier through city gridlock to reach rural paradise.
Catching up with Marc at his local Hayama coffee shop gave us a welcome breather.
Most of our morning pedaling took us through the Shonan and Miura Peninsulas toward the ferry, but the real test came during the second half down Chiba’s Boso coast in full typhoon-like conditions.
After waiting out the worst of it in Tateyama, we ground our way up one last steep hill to our wood cabin, arriving soaked to the bone and completely spent. Strava claimed we did 89k—though the actual distance was only 53k—proving once again that GPS trackers love to add insult to injury when you're already suffering.
It was an absolute pleasure catching up with Jan, Josh, and their wonderful family in Tateyama. It’s been far too long!
Thursday | Day 3: Tateyama to Asahi, Chiba
This was the longest leg of the tour. The flatter terrain helped, but by the 70k mark, everything in my body was stiffening up. I hit a brutal wall at 90k, and another at 110k post-lunch, but Makita powered us through the final 30k home stretch. Miraculously, the sun finally made an appearance, keeping us dry the entire day (aside from our own excessive sweating).
Riding the Boso coast along the Pacific was one of my main motivations for planning this tour, and the stunning views along Kamogawa, Katsuura, and Kujukuri did not disappoint. We bypassed Onjuku by taking an inland mountain pass to dodge traffic, though navigation proved challenging because I hadn't managed to sync Google Maps to my bike computer. It took a full day of directional torture before common sense kicked in and I finally fixed my brain fart on the last morning.
Route 30 runs slightly inland from the ocean, making for smooth, uninterrupted sailing from Kujukuri to Asahi over the last two hours. Even so, my legs were in absolute agony for the final 50k, and the thought of the hotel onsen and a hot meal was the only thing keeping the pedals turning. We finished with 144k, 817 meters of climbing, and 6:16 hours in the saddle—a stat line that looked great right up until I tried standing up from my chair.
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Friday | Day 4: Asahi to Tsukuba, Ibaraki
Friday morning started with a trip down memory lane at Choshi Marina—the site of past triathlon glory—and the easternmost point of Kanto.
Makita-san had to split off back to Shimoda after Choshi, leaving Thomas and me to tackle the final leg to Tsukuba. Having finally mastered my new Wahoo navigation system, we enjoyed smooth sailing along the Tone River up to Lake Kasumigaura. The traffic-free river path was a absolute dream, and looping around the peaceful lake felt like a gentle victory lap to wrap up the journey.
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We logged 122k with a pancake-flat 304 meters of climbing in 5:05 hours. Morning in Choshi was fantastic, and wrapping up with some post-ride diving in Tsukuba made for the ultimate finish. Huge thanks to Makita-san and Thomas for the incredible company and for showing world-class stamina in enduring my endless stream of bad jokes.
I hauled the bike onto the train in a rinko bag for the 5-hour marathon transit from Tsukuba back to Tokyo and down to Shimoda. Sitting motionless on a train seat for five hours turned out to be the hardest leg of the entire trip.
Grand Totals Over 4 Days:
Distance: 450 km
Energy Burned: 10,000+ calories
Prefectures Visited: 4
Peninsulas Covered: 3
Tired Legs: 2
Happy Camper: 1
