The Plan

How do you decide where to go? That’s a question I’m often asked about my nomadic travels since July 2015, and also about how I planned this road trip.

The answer: It came together organically.


I originally aspired to draw inspiration from the above algorithm (click map for the interactive version), but in the end it didn’t speak to my independent nature.

Sometime between talking about the road trip and planning it, I also committed to speaking at two conferences in Orlando and Seattle and representing my company at another in Napa Valley. This influenced the timeline of the itinerary but not the route or stops I wanted to make.

From there I used a blank map on and began plotting a route from California to Orlando, then Orlando to Chicago and Chicago to California via Route 66. The process went like this:

  • Pick cities
  • List landmark hotels I wanted to stay in, e.g., Blue Swallow, Galt House, The Campbell
  • Select approximate dates
  • Reserve/book hotels for the rest of cities
  • Adjust – There were two sets of revisions during the process, and refinements are still made on the road as circumstances arise — unforeseen weather, work, airbnb and security issues.

This is the third iteration of my map, but it’s since been revised. Again.

I’ve heard that people take months to plan a trip like this. A rough guess is I made 200+ decisions in the space of 48 hours, and it was done.


In the spirit of freedom, many opt to wing it and move through their road itinerary without reservations or a schedule. That’s not my approach because I’m a woman traveling alone and safety is a concern; I also have childhood memories of my dad’s spontaneity landing the fam in roach motels or sleeping in the family van. There’s nothing romantic about roaches, I assure you; and sleeping in a car alone sounds meh.

Booking ahead also means having the best selection of accommodation for lower cost, not to mention it’s required for places like the Grand Canyon and Yellowstone.


How much road will I cover? According to TravellersPoint maps, I’ll end with 7,100 miles or 14,500 kilometers.

I also used total mileage to calculate the approximate cost of gas, though prices can vary wildly between $2.09 to $3.79/gallon, and road and weather conditions can impact mpg.

Edit: In the end, I drove 10,000+ miles!

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