Some people plan extensively, others leave it to chance. There are pros and cons to both approaches and you generally do what suits your personality. Planning ahead allows you to source out the best routes and cheapest accommodation. It decides the day's riding months in advance and it takes away that process of decision-making once you're out there riding. The downside of course is the inflexibility of it. If you stumble across a new route or place to stay, but you already have tonight's and the next night's accommodation booked, then you can't divert.
For my Iceland trip, I left it a lot to chance, as much of it can depend on the weather. In advance I'd mark some of the roads I wanted to ride, as well as some of the key destinations, and use that as a reference point once there. The beauty of Iceland is in being able to legally wild camp, not to mention the near 24-hours of daylight, so you don't get nervous when it starts to get dark and you don't have anywhere to stay yet.
A lot of this comes with confidence. On your first trip it's understandable to over-plan, but the more you do it the more you'll trust yourself to sort things out as you go. But possibly more important than planning is research. You might not have everything laid in place, but if you've fully researched the options and procedures – be it border crossings or accommodation facilities – then you can leave in the knowledge that you’ve done all you can to deal with the possible problems along the way, rather than relying on an outright plan. When I rode back from Australia on a bike, I only had two days to actually get ready for the trip – prep the bike, sort out documentation etc – but I’d spent a year researching the route so knew that when opportunity did suddenly present itself I had the knowledge I needed to set off and make the plan from there.
Read all of BikeSocial’s motorcycle adventure planning tips here.