Booking ahead didn’t work as well as expected. Reserving hotel rooms more than two days in advance was a bad idea for us. Deviations in course, time and attention left us riding extra miles on more than one morning, trying desperately to arrive at an accommodation we had hastily booked a few days prior. Airbnb is not the best idea if you have a loose itinerary. Their cancelation process is cumbersome and many people don’t want to waste time reserving, canceling and relisting their place, which is totally understandable. Roadside hotels, however, were the ticket. As I’ve learned on countless road trips, if you stay just outside of the city and are willing to sleep in something where the name ends in a “6” or an “8,” you will almost certainly be able to secure a room. Now, that’s not to say you shouldn’t book ahead if you have to, or in our case want to. Some places you just must see and stay at. The Shady Dell in Bisbee, AZ or the Columns Hotel in New Orleans, LA; the Ocean Key Resort in Key West and the Coombs House Inn in Apalachicola, FL were all worth the extra effort, and the extra miles. My suggestion? Pick a few that you absolutely will not miss, or perhaps have to have, and then roll the dice on the rest. It’ll work out, I promise.