I have to say the more people that post on this thread, the more amusing it becomes. Riding all day and all you see are trees is boring ? Well I suppose at one point after 44 yrs of living in Maine, I might have agreed with that. Then I moved to SoCal and found out that anytime you want to go anywhere other than up PCH, you have to ride through the desert. And mile after mile after mile of nothing. Now the 1st time I came down off of I-40 out of Flagstaff and got to a point below Needles where I could see forever in any direction I thought "how beautiful " Then I went on a long trip that involved two days in the Mojave and learned that that beauty can be damn near fatal. So I've learned to ride in the desert and at times do still look at the sunrise in awe as Forest Gump described it "where you can't tell where the earth ends and Heaven begins" BUt when you've ridden 2500 miles and you're still 800 miles from home and you know most of it is desert, it's - - -well it's tough some days. Then there's days where you ride all day in the rain. If you're prepared, you can be warm and dry but 400 miles of riding in the rain can leave a knot between your shoulders that even the best massage from your BSR won't get rid of.
So long distance riding is always a bit of good times and bad. The wonderful thing about us Homo Sapiens is that we have this inate sense of being able to look back at those tough times and see them in a more humorous or less painful light. When we did the Western GTG in Sedona, I must say the day we did a group ride in the cold and rain sucked a bit. BUT, we got back to the hotel and laughed about it and it became part of why we all had such a good time on that trip.
When all is said and done, you just have to get out there and ride. 100 miles, 200 miles, 300 miles, 1000 miles - -as noted in other posts, whatever feels right for you. The more you ride, the more you want to. When you get home from a 7,000 mile round the USA trip you swear you're never going to do it again; but a week later and you're already planning your next one. I don't know if H-D Inc had this in one of their ads or where I heard it, but " It's all about the ride " - - - -as well it should be.
B B