Robert, James, and I completed this route in July of 2018. A huge shout out to James for routing this trip.
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We flew from San Francisco to Sapporo (transferred in Tokyo) then caught the train from Sapporo to Abashiri where we officially started riding.
We headed East to spend time at the Shiretoko National Park then backtracked to Shari. From there we went south to get on an inland route west until we reached the coast at Tomamae. Then we went North to get to Wakkanai and took the ferry to Rishiri Island. We finished by taking the train from Wakkanai to Sapporo.
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This trip was almost entirely paved. There was only one small section of gravel that we had to walk ***TODO*** and a couple of dirt patches around the bike paths. The roads in Hokkaido were mostly quiet and even highway traffic does not move as fast as it does in the United States. Plus cars/RVs/trucks are all generally smaller and drivers were polite. We met a handful of other cyclists on the road–mostly Japanese with some New Zealanders and Australians.
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Even though Hokkaido is remote in comparison to the rest of Japan, it is still fairly dense. We were never far from a town or food source. And even the most remote roads would have a vending machine somewhere nearby. Along the roads, we often saw Michi-no-eki’s which are highway rest stops. They have food, bathrooms, visitor services, and a market that sells local food products. We stopped in many of these and because they cater to tourists, there are a good representation of the local area. The campgrounds always had space and we didn’t need to reserve anything in advance except for the first/last nights in Sapporo and the nights in Asahikawa to be safe.
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 Hokkaido is generally dry and sunny in July. However, when we went, we caught a freak typhoon the first few days and were riding in the rain. It was so bad that we had to cancel our plans as the roads were flooded and trains were not even operating. However, after it passed, the sun came out and we had some really gorgeous days. In general, the area is pretty damp but the reward is lush green hills. Wakkanai is the northernmost town in Japan and that area was pretty windy–especially the ride to Cape Soya.
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We used a combination of our phone apps because there wasn’t one go-to solution.
Google Maps – general GPS info, road names, points of interest, food/lodging info.
RideWIthGPS – contained our route.
Maps.Me – offline maps. Japan restricts the download of offline maps on google.
BikeRoll – additional elevation info.
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We bought our Japan Rail Pass online ahead of time. It saved us money and the hassle of doing it in Japan and using our precious time there. Here is a good resource for deciding whether or not you will benefit from a pass.
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As a naive American tourist, I seriously underestimated how difficult communication would be. I assumed we’d be able to handle most situations in English well enough, but that was not the case. Many people, especially in Hokkaido and the more remote areas, did not speak any English. For anyone planning on going to Japan, I strongly recommend taking advantage of any logistics ahead of time.