This post is the summary of my travel plans, reasoning for it, and some technical details.

The transition to a digital nomad has happened successfully. I’ve moved out of my apartments, stored/threw away/donated my belongings, and left San Francisco. With friends, we stayed a week in Santa Barbara and spent the whole July in a nice tropical-themed house in San Diego. Then the question appeared: where to next?

As you remember from the previous post, my company has said we’re going to be in WFH mode until Labor Day (Sep 7, 2020). Last month, this policy was extended until the end of 2020 with a few clarifications: you can temporarily relocate within the US, but be available during the normal working hours of your team; you’re expected to return to the office in January 2021; and we don’t recommend traveling outside of US due to the possible restrictions at the border. This prompted an idea of a road trip across United States! I’ve been to quite a few US cities in the past years, but there are still many more unexplored ones.

Usually long-distance road trips span several weeks. E.g. traveling coast-to-coast can take about 50 hours or 6 days of 8+-hour non-stop driving each day; but where’s the fun in that? According to the internet, assuming you stay in the points of interest for a few days, a memorable trip takes 3-4 weeks (2-3 “resting” days per each “driving day”). However, in my situation I would have 5 months before I’m summoned back to the office. Of course, I should also work remotely as I’m a full-time employee.

(Side note: actually, this week the company WFH policy was extended again, until the end of July 2021. Google and Facebook also announced their extensions until the same dates a couple weeks earlier.)

So, the plan was hatched: I can start from San Diego, stay each week (or two) in a new place, drive on weekends, work during the weekdays, and be back in San Francisco by January. I’ve reasoned that I can comfortably drive 6 hours per day (this turned out to be pretty accurate). So I can construct a route with the week-long stops up to 12 hours apart (and stay in an intermediate point on Saturday night if needed).

I opened Google Maps and started to pick cities that I’m interested in, never been to, or at least heard something about. I decided I’ll go in the clockwise direction, because the South is too hot in summer, and the North is too cold in winter – we’ll see how that strategy works. Here is my itinerary. There is some buffer, and I don’t need to be in SF in January anymore, so I have quite some flexibility. Please let me know if I should absolutely visit some city that isn’t on the list. You can also let me know that I should absolutely NOT visit some city, but then offer a better one nearby :)

  • August
    • San Diego, California
    • Las Vegas, Nevada
    • Salt Lake City, Utah (1 week)
    • West Yellowstone, Montana
    • Casper, Wyoming
    • Denver, Colorado (2 weeks)
    • Rapid City, South Dakota
    • Fargo, North Dakota (1 week)
    • Minneapolis, Minnesota
    • Milwaukee, Wisconsin (1 week)
  • September
    • St. Louis, Missouri (1 week)
    • Indianapolis, Indiana (1 week)
    • Cincinnati, Ohio
    • Cleveland, Ohio (1 week)
    • Upstate New York (1 week)
  • October
    • Boston, Massachusetts (1 week)
    • Portland, Maine (1 week)
    • New York City (1 week)
    • Washington, D.C. (1 week)
  • November
    • Norfolk, Virginia
    • Charlotte, North Carolina (1 week)
    • Nashville, Tennessee (1 week)
    • Birmingham, Alabama
    • New Orleans, Louisiana (1 week)
    • Houston, Texas
    • South Padre Island, Texas (2 weeks)
  • December
    • Austin, Texas (1 week)
    • Amarillo, Texas
    • Albuquerque, New Mexico (1 week)
    • Phoenix, Arizona
    • Los Angeles, California (1 week)
    • San Francisco

Map of the trip

I decided to search the week-long stays on Airbnb, and book the overnight stays on On Airbnb, I put in the dates from Sunday to Saturday (or the next Sunday – depends on whether I need to drive both weekend days), filter by “has A/C” and limit the price by $100/night (my inspiration is to fit into $3000/month, which is comparable to what I would be paying for a 1-bedroom apartment, had I stayed in SF). Then I check the location (walkable distance to “civilization” like restaurants and grocery stores), photos, and reviews. For some reason, Airbnb doesn’t include the service fee/cleaning fee in the per-night price, so the lowest-price place might not end up being cheaper!

Another gotcha is non-“instant booking” listings: one time, I submitted a request to book the place, and Airbnb told me that I’ll get a response within 24 hours… except that 24 hours later, there was no response from the host at all, and my request just expired, while I needed a place to sleep tonight. I’m not sure what is the expected behavior here (apart from booking far in advance): if I attempt to book multiple places in parallel, Airbnb warns me I can be double-charged. I’d like to be allowed some redundancy, with the first-response-wins or another strategy.

Of course, to do a road trip, you need a car. In San Diego, I’ve bought a certified pre-owned 2017 Toyota Prius. Thanks to my amazing friends for helping with negotiations – that was a memorable farcical process. Pretty happy with its fuel efficiency: I can travel about 400 miles on a full tank (9 gallons), which costs about $20. Did you know that California has the second most expensive gas in the United States? Only in Hawaii it’s more expensive!

Another concern is the ongoing pandemic. In United States, the number of new daily cases is staying high, and the preventive measures are varying from state to state. Many indoor sightseeings like museums and cathedrals are closed, but many outdoor ones are open and operating. I’m personally trying to stay as safe as possible, wearing face covering, ensuring distance from other people, and so on.

Finally, follow my photoblog:!