Trip planning is as easy or difficult as you want to make it. I break it down into three categories: Price, destination, and “just go”.
You have a certain amount of cash to burn and that’s it. The first thing you need to do is figure out what your cost per mile is. It starts with your fuel consumption. If your bike gets 50mpg and gas costs about $4 per gallon then your fuel cost per mile is $0.08. Lets say that you have $100 to spend and Saturday and Sunday to ride. At .08 per mile you can go 1,250 miles if you eat and sleep for free. Armed with that, you can draw a 600 mile circle around your house on a map and go anywhere you want in that circle. Add in a buffer of 100 miles and you can safely go 500 miles one way for your trip.
Now that you have that, you can tailor your trip to a destination inside that circle, adding money or subtracting miles based on what you want to do on your trip. If you are heading to BLM land and are going to do some hiking or photography or any other “free” activity, camp at a free BLM campground, and bring all your food, then you can use your entire budget for fuel.
If you want to go to an amusement park, concert, motorcycle event, etc. then you will have to factor in the entry cost into your budget. That cuts into your fuel, shortening the distance you can go. The same goes with eating out, and staying in hotels or campgrounds with fees.
When it comes to trips based only on price, I would have at least a 50% reserve on shorter trips for unexpected problems. You can drop that percentage based on how far you are going and the chance of issues. A RTW trip has a very high chance of issues, but the mileage is so high that it would be unrealistic to have that much reserve cash.
This is a bit easier to budget. Just figure out where you want to go, and how you want to get there. If you want to super slab your way across the lower 48 from New York to L.A. you can easily figure out the fuel cost. Then figure out how many miles per day you want to do, and you know how many nights you will need a place to stay. Add in the food, leave some extra for unexpected costs and you have your total cost of the trip. Even if you want to take all backroads and add in a bunch of stops, you can find out the cost of anything you want to do well before you leave.
This one isn’t for the faint of heart! All you need is a phone and a debit card. Leave the map at home, and just go! Ride until you are tired of riding in whatever direction looks best. Many great adventures can be found by riding this way. Not much else to it!
The length of the trip, the amount of cash you have to burn, and the time you have to spend will dictate which methods you use to plan your trip. The bottom line is get out there and have an adventure!