Skip the airport. It’s time to plan the perfect road trip.

Somewhere between San Luis Obispo and Monterey, California, I wondered if the rain would ever cease. Pounding storms had followed me on my two-week solo road trip from Los Angeles to San Francisco, so much so that the Pacific Coast Highway was closed to motorists through Big Sur — one of my planned pit stops. While I meticulously planned the drive and itinerary down to the hour, I never once considered a backup plan for something as common as a closed road. At a loss for what to do, I scrambled...