Digital Nomad: Road Trip While You Work

They say remote work has its perks–work from home, work in your pajamas. For me, working from anywhere is what gets me excited. At WebDevStudios, we are distributed, so I take advantage of it. Last summer I got accepted to speak at WordCamp Miami. I had wanted to go back to Florida as that is where I spent my teens growing up. I wanted to visit a few friends and do a vacation at the same time. So I rolled WordCamp Miami and a summer trip all into one.

I was only taking a five day vacation (Disney World) and was going to be in Florida for about a month and I wanted to wander around the country. There were a few challenges: where to stay, how to get around, and how to get work done each day. I started doing the math. Do I fly to Miami and rent a car? Stay in hotels? Airbnb? Camping (which I do a lot)? Then, I started thinking maybe I want to travel a bit longer and tour the country.


My first order of business was to figure out method of transportation. I did the math for a rental car but, when combined with the cost of accommodations, it was more than I wanted to spend for a month or two of travel. Uber is fine if you are staying in one city but I was digital nomad-ing across cities and even state lines. I looked at motorcycle rentals. They are as much as or even more than a car. It’s not the same as other countries where you can get a bike or scooter rental cheap–there’s definitely novelty pricing here. I own a Vespa and its a modern scooter with a motor that can do slower freeway speeds–it will cruise all day at 75 mph. I frequently drive the Vespa on smaller road trips, and thought, why not? I looked at pricing to ship the Vespa to Miami. The cost to ship it was the same as renting a car for a week. So, Vespa it was.


With transportation out of the way, I needed places to stay. You become a master at finding great places for less when you live the digital nomad lifestyle. Your iPhone or Android is your BFF: Download Yelp, hotel apps, Airbnb, camping apps, and any travel app you can find.

Generally, I’m not the type to plan too far in advance. I go for the adventure and let the winds take me. If you stay in offbeat locations, you can get better deals–like the rundown old children’s home in New Orleans that was supposedly haunted (where I stayed for seven days). Or the brand new five star hotel in a hole-in-the-wall Texas town that I stayed in for for $39 bucks a night. The shower had two heads and I was the first person to use it!

Hotel Tonight is a good site to snag those rooms that hotels don’t book and they want to fill. On a whim, I bought cheap camping gear and stayed at the Grand Canyon and a few other camping spots to offset the cost of hotels. The key is is to not get hung up on places to stay, or the idea that you need to plan every last detail–especially if you are taking a longer trip than a few weeks. If you are traveling by car, you can also always pull over and take a nap.

Roadside Attractions


So I had transportation and knew I could get places to stay without too much fuss. The next big challenge was when and where to work. Sometimes I would need to drive a few hundred miles in the morning before I got to a work spot–which added to the adventure. By far, the most reliable workspace to find is a Starbucks Coffee; they have adequate wifi, food, and coffee to keep you going all day. In some places, Starbucks is the only cafe you’re going to get. Other cities have awesome local independent cafes and co-working spaces, and if you can, I highly recommend you find those.

When you get somewhere new, talk to people! Get information from them on what to do locally. You can also generally rely on libraries, which usually have free wifi and do not care if you are there all day long. There’s also a McDonalds in every city in America and most have free wifi; who would have thought?

And, of course, your hotel room. When I stayed at the Grand Canyon, the KOA campground had the fastest wifi I think I have ever even used. I was coding up client work, in a tent, in the rain! When I was done working, a national park was there waiting for me to explore. Beats fighting rush hour traffic after that nine to five!


I had the challenge of only being able to carry a small amount of stuff because I was on a Vespa. Scooters in general have a good amount of storage but nothing like you’d get in a car. Even in a car, you have to prioritize what you’re bringing. One of the tenets of digital nomading is the idea of leaving it all behind and living a minimal existence–to not worry about material things and experience the world around you, rather than focus on your latest “toss it on a shelf.” That being said, you gotta have your tech gear to get your work done.

I have a small bag–my work bag. This bag contains everything I need to get my work done. I highly recommend putting together a bag that has everything you need so you can just grab it and go. My bag is really small–a Swiss Army day backpack. I can fit an 11″ MacBook Air, iPad air, Android phone, iPhone, back up USB hard drive, and a few backup power packs and various cords to plugin. This one small bag is the only thing I need on an entire trip. You could buy clothes and food if you need but your work bag should be treated like gold. The other item that is a must have for a digital nomad road trip is a mobile hotspot. In most areas the wifi is fine, but I have been in a few hotels and cafes where I couldn’t get a webpage to load. Get a “pay as you go” hotspot plan. I got one that has roll over data and its on auto pilot for top ups. I have so much data stored up I could watch Netflix for days, in a tent…in the rain!

Grand Canyon

Do It!

At first I thought I couldn’t do a digital nomad road trip that long, and certainly not on a Vespa. You may think that too. Remember: Countless others have already been there and done that. I’m here to tell you if you are a remote worker, you owe it to yourself to see the world. You CAN work from anywhere. I honestly believe that knowing that when work is over, I can go out and experience new things has benefited my ability to stay focused on tasks and get things done. It makes my life a prize for getting my work done. Get out there and experience it!

Bon voyage!


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