I like very long trips, and I plan them in detail. My trips include dirt roads that I am unfamiliar with, so I draw tracks from my electronic maps and load them in my GPS to follow. I usually fly the route on Google Earth before I go. Most of the time they go through, but I have been stopped by water crossings and washouts too.
My trips call for making specific overnight destinations and fuel tops too. Out west you never want to pass an opportutnity to fuel after about 140 miles. Put those things together and I find I need a certain pace to make my schedule. That can be quite entertaining on some of the forest and farm roads along the way.
My dual sport trips typically call for 200 to 350 miles per day, depending on the terrain. XC trips on the slab call for 500-650 miles per day. I like to go coast/coast in 8 days with a few explorations thrown in for a day or day and a half.
For me the fun is making the route and schedule in advance, and then riding it. I try and predict arriving at way points within a few minutes of a target time. It's like a game.
The best trip for me has been the Alcan 5000 TSD rally. It is uber organized and requires hitting specific spots on time. We have chase trucks that haul our spares and luggage. The event is about 4600 miles over 9 days, starting from Seattle and finishing in Fairbanks. There are 2 or 3 timed sections each day, but you never rest because you have pre-determined starting times to make at each timed section.
I've entered twice and am entered in the next one in 2014. The club lays out the course and give us our road books the night before. It is quite the challenge. Then after the victory party, I ride back to Seattle, which is about 2700 miles. I do that in 3.5 days.
Here is the itinerary for 2014. We'll have about 50 motorcycles and 20 cars as starters:http://www.alcan5000.com/2014itin.htm