We've traveled and traveled and traveled. We've gone coast to coast 3 times, also up and down the East coast extensively. In our experiences when you are in the high traffic areas like Yellowstone NP, San Diego, Yosemite, even Elko, Nv (a great stop over point coming back east) it is safest to make a reservation. I often make the reservation for a couple of extra days then adjust as necessary. We like full hook ups when we are traveling (we stay for 2-3 in Key West dry camping without issues). We like to run our washer/dryer and both ACs in a well kept campground. So we like reservations as we can.
Relative to using Trip Wizard, we love it BUT I am a bit of a planning freak and spend hours making sure of the route. I often Google looking for recommendations on various routes. State and interstate highways are generally okay. If it has a county designation - be VERY careful. For refueling we use Gas Buddy and the distance feature in Trip Wizard. I don't like getting into a fuel spot that doesn't have enough room to get in and out of without unhooking the toad!!
Hope this helps.
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US Army Retired - Loving The Road Trip
Challenger 37TB
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