We went on two tours this year, one for 19 days and the other for nine.
First trip: I started with a vague plan, from Calgary south to Bozeman and Yellowstone for a few days, then across to the Black Hills for another few days, and then back again. Normally, we ride for an hour and stop for a few minutes before resuming, we eat lunch and often supper in restaurants, stop to check things out, stop to take pictures, and we never start as early as we want to. Very laid back --- it's a holiday. On average, we cover 200 to 250 miles in a day, so that's how I approach my trip planning, one day at a time.
I scope out our route using google maps to determine where we are likely to be, then scope out motels in the area. I keep a shortlist on my "itinerary". At some time in the day, usually early afternoon, we will decide how far we will go and I will call ahead to book a room. My wife rides much easier when she knows there is a room waiting for us not far away. At this point, we have regular stops, motels located 200- 250 miles apart spreading out radially from Calgary through BC and Idaho and Montana.
As for the itinerary itself, that sometimes gets thrown out the window. We got fed up with the traffic in Yellowstone, so we left for the Black Hills a day early (good idea!) and again, opted to head back home a day early rather than tour the Badlands (good idea - an excuse to go back!). This last trip, we had three or four days in Idaho before we rode Lolo to Montana, where we had another three or four days. Again, once we were there, we decided not to go into the Palouse again and instead headed to Missoula a day early. All that matters, every time, is that we are back home in time to land safely and be ready for work on Monday.
one 125 Vino
two 650 Burgman Execs
Vulcan 900 Classic LT, V-Star 1100 Silverado