People have asked so I will try to answer the question about how I planned and managed this big road trip.
I started out with two specific goals with locations and dates. I wanted to attend the Key West Literary Seminar in early January, and I wanted to attend the bat mitzvah of my dear college friend Jonathan’s granddaughter Ava in Boston in late January. I began with housing reservations in both places. I initially made no plans past the bat mitzvah because how long I stayed in New England would need to be very weather dependent. There was a rainstorm on the pacific coast in the first week that caused me to drive slowly. I had one long stop planned in Pensacola, Florida and had hotel reservations at the start of my trip but beyond that I mainly drove east from CA to Florida sleeping in rest areas (in my car with a pillow and blanket) and driving as far as I felt like going and stopping when I got tired.
After Key West I made reservations for hotels up the coast to Boston but also kept an eye on the weather intending to stay ahead of any ice storms (or being prepared to stay back to wait until the roads cleared). I had already reached out to old friends in Vermont, New Hampshire and Massachusetts and when the weather seemed to allow it after the bat mitzvah I made specific plans and reservations. Finally, when they started predicting a major northeaster was on the way I cancelled remaining plans and got out of the area and ahead of the storm as quickly as possible.
I had decided very early on that I would not try to return home via I-80 and the northern route and would instead drive back South even if it added another 2000 or so miles to the trip. It was not just the “safety” of being off the road during any snowstorms but also a matter of comfort and personal pleasure. So now I am back in South Florida at the end of week 7 of the trip and starting to plan the final three weeks. I enjoyed my stop in Pensacola on the way here and will try to plan another few days on the beach there before I start the final legs of the trip. I am hoping to visit New Orleans for a few days. I will try to delay and avoid the bottom of the current storm that is bringing cold weather and rain throughout Texas and if the weather is nice maybe stay in the desert near Tucson