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10 Things To Know Before Your "Work from the Road" Trip

Updated: Feb 22, 2022

girl walking along the center of a two lane road in California

The beauty of road trips is they can be completely unplanned or planned to the minute. Regardless of your style, here are some tips to get you set up for success that don't require a ton of effort or money and pay off big time. Below are my top ten favorite suggestions for getting your set up right for your work from the road trip!

1. Plan loosely using can't miss destinations

A great way to plan a roadtrip is to use the destinations you most want to see as your loose point to point guide and letting the in between stops and sights just happen. This will give you the tiny bit of direction you need to feel like you're getting the most out of your trip without having to slave over a step by step itinerary. Try the Roadtrippers app to plan it out visually or get recommendations about what to see!

2. Think through your money strategy

Don't let money stress you out. Even if money isn't a big consideration for you, taking a moment to think about how much you'd like to spend either in total or daily can help you get a loose sense of if you're in a reasonable range. If you are hoping to keep to a budget, download Trail Wallet to track your spending. You can set a daily budget or a total trip budget, easily input expenses and always check how you're tracking with their simple interface. I used this while on a backpacking trip for 7 weeks in South America and ended up using it for my monthly budgeting for the next year because it was so easy!

3. Get a handle on your portable work station and coverage in your area

This IS a work trip after all. I wrote a separate post about the items I use for my perfect portable work station that I've figured out over the last few years. Having a better set up than just your laptop takes the stress out of working in unfamiliar locations. I use a folding second monitor, wireless keyboard and mouse, and computer stand that all collapse and fit into my backpack. I even have a tabletop standing desk converter that I can throw in my trunk, and I use this whole set up as my home office as well!

You can also figure out your WiFi and cell coverage situation by visiting WiGLE and/or downloading the Coverage? app to get a sense of the coverage level in the areas you're heading into so you can plan when to take your calls and when you might be out of touch.

4. Bring breakfast and lunch foods with you in a car cooler

Again, I'm all about keeping things simple but setting yourself up for success. There are some easy things you can do to make your food situation healthier, tastier, and less expensive. On my PCH roadtrip, my friend and I brought along a mid-sized cooler for our car. We stocked up on groceries for breakfast and lunch and just brought it in to our accommodation's fridge at night. This will save you money and you'll be able to eat your favorite foods, not just what's convenient (think foods like bread, cheese, peanut butter, apples and jerky). Then buy fresh supplies at farm stands or farmers markets as you drive by. Fresh avocado, tomato and cheese sandwiches with your Sonoma winery tasting just hit different.

5. Use packing cubes to organize your bag

Packing cubes really help you find what you need quickly when you're packing and unpacking frequently, which you will likely be doing while traveling.

6. Put GPS trackers on your most valuable items

Speaking of packing and unpacking frequently, if you lose things easily (like I do), being on the move is going to increase your chances of leaving something behind. Grab a few GPS trackers from Tile for your wallet, keys and anything else you can't live without that can't be tracked via FindMyIphone. This way you can at least backtrack and get your stuff, even if it's inconvenient it's better than the alternative.

7. Think creatively about finding accommodation with reliable WiFi and a good work setup

AirBnB and VRBO are great places to start to find unique stays, but WiFi and other accommodations are going to be inconsistent and might require a lot of research. Don't discount cheap hotel chains, which can often be booked last minute (think HotelTonight) or using your credit card or hotel points. Guaranteed to have good WiFi, a desk setup, and maybe even breakfast included, and flexible checkout times for when you have to plan around meetings.

8. Download a few camping website apps to find the best places to camp on weekends

If you're planning on camping or have your own sleep situation in your vehicle, download iOverlander for info on rest area amenities and places to "wild camp" aka park/camp overnight in a non-designated camping area. HipCamp is also a great resource for booking campsites and many other outdoor accommodation types.

9. Optimize your car setup

Ok I hate the word optimize, but honestly, your car is going to be your quasi home, so make it work for you! Outfit your car with a good phone charger, phone stand, hanging trash can, and think about getting a WiFi extender. This way you can stop on the side of the road and beam that Starbucks WiFi straight to you in the parking lot for a work call you couldn't reschedule without all of the background cafe noises or having to wear a mask.

10. Listen to relevant audiobooks or podcasts about the area you're driving through

It's like a personal audio tour! Download some podcasts or buy some audiobooks on Audible or your local library. Think about where you're traveling through and try listening to relevant topics so you're learning about what you're seeing! For example, I listened to episodes of Unfinished: Short Creek while driving through Utah. If you want to be inspired about nomadic living, check out my post on my favorite Dreamy Nomad Inspo Audiobooks.

I also recently learned about HearHere, an audio tour app that is location-based, telling short ~3 minute stories about the things you're driving past!

Lastly, have fun! If you miss a stop or get off track, don't stress, there's always going to be more to see than you have time for!

Happy Trails,


Disclosure: This post contains affiliate links, which help keep Pollen Travels going strong! I will only ever recommend products I have tried and love.

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