Hokkaido is... different. That's what you'll read in all the guidebooks, that's what you'll think when you see the photos and that's what you'll feel when you step off the ferry or airplane. And it's true. However, Hokkaido is still Japan - so if you believe the hype and go there expecting the "Wild West" of the East or something, you may be let down. So give it time... and go beyond the surface. Yes, Hokkaido still has cell phones and convenience stores, and the urban areas (including some of the roads you'll be cycling) look pretty much like any other part of Japan. Until you look at the foliage (totally different), the local communities (markedly distinct), the landscape (vastly diverse) and most everything else... and then you realize you're definitely not in Kansas - or Kansai - anymore. To give one practical example: keep your mouth closed when cycling in mountainous areas - the number of insects flying around is truly astonishing. Take the time to eat the regional specialties, and not just the corn and potatoes. And by all means spend at least one night at a Toho-yado or even a Rider House - both virtually only-in-Hokkaido institutions. It won't take you long to see how different -and special - Hokkaido really is.
This long but rewarding route travels in a huge arc across the island, from Hakodate in the south to Shiretoko in the east, and manages to pass through both major cities (Sapporo and Asahikawa) and most of the other major tourist destinations on the island. You can do it in a little over a week... but we recommend you devote as much time as possible to your Hokkaido trip. Even if you don't, not to worry - you'll be back...