We booked a hotel ahead of time for the first night only. We did not want to be hindered by any deadlines for hotel reservations, so we did not book any hotels ahead of time. There are hundreds of hotels close to the highway so finding a hotel last minute was a breeze. We would stop when we found a town we liked or when we were too tired to keep driving.

We wanted to rent a convertible for this epic road trip; however, we ran into some trouble. All of the car rental companies would not let us rent a convertible in San Francisco and drop it off in L.A. This rule was only for convertibles most likely due to the popularity of renting one for this specific drive. We ended up renting one anyway. We had to alter our plans to include driving back to San Francisco and have our flights at the same airport.