We’re laying out plans for another cycling trip, and we’ve got our sights set on a big one: a 20K+ mile (32K+ km) route from Deadhorse, Alaska to Ushuaia, Argentina. After pondering lots of options, we’ve settled on a tentative route with a diverse mix of dirt, gravel and pavement. But there’s more to consider than just the direction of travel. Many sections of the route have limited seasons for comfortable bicycle touring. And some areas, like the Darien Gap, should be avoided for other reasons. In this blog we lay out some of the key timing and planning issues we considered, and how they could affect our overall bikepacking trip.