In August 2019, Jonathan started working in a new, fully remote role. Since I (Kelly) had been working from home as a copywriter for about 4 years, this made both of us remote workers for the first time.

Inspired by two friends who were driving around the United States on an extended road trip, visiting the top golf courses around the States, we started thinking about traveling more ourselves.

Until this point, travel for us looked similar to how it probably looks for many people: you get so many days or weeks of vacation each year, you drive or fly somewhere, spend about a week or two in that place, then head home and wait to do it again next year.

But, and maybe you can relate, despite having a few weeks of vacation from our jobs each year, we hadn’t actually taken a week-long vacation (with 5 consecutive days in a row off) since our honeymoon 2.5 years prior.

We were busy working on our careers and even canceled multiple trips to take new jobs or new roles.

So, when we were both able to work from anywhere, we started daydreaming. We were watching our friends work from an RV and travel around the country doing something they loved and wondering how we could attempt something similar.

We weren't quite ready to go all-in with an RV, but we do have a dog who expects to tagalong everywhere we go, so we figured we’d test out a few roadtrips, driving our car and staying in short-term rentals or hotels along the way.

In September 2019, we experimented with a week-long road trip to Jon’s hometown of Virginia Beach, Virginia. Then in November 2019, we experimented with another road trip, two weeks in North Carolina.

The Road Trip Experiment

We knew we loved road trips - in 2015, we took a 10-day road trip from Seattle to Crater Lake National Park to Yellowstone National Park to Glacier, and back to Seattle. But that was a traditional vacation where we flew to Seattle, roadtripped for 10 days, and flew out of Seattle back to the East Coast afterward.

This would be different.

We’d drive to Virginia Beach for the week while working. And for this week, we’d be staying in a hotel on the beach so we would work from the hotel during the day and then walk along the beach after work.

(Spoiler: A one-room hotel room was on the small side for us as two people working full-time with a dog. Just one thing we learned along our roadtripping experiment to figure out what works best for us. You can see how our road trips have evolved in 2020, 2021, and 2022. More to come on what we look for when finding places to stay for a mix of travel and work!)

November 2019: Two Weeks in North Carolina

After our week in Virginia Beach, we went back home to Maryland and started planning our next experiment: What if we hit the road for two weeks and visited someplace new?

So in November, we doubled up our road trip itinerary and packed our bags for a two-week road trip through North Carolina. We’d spend one week in Raleigh and one week in Asheville, North Carolina.

Stop #1: Raleigh, NC

We planned our first stop near Raleigh mostly to visit friends. That was one thing we were excited about with traveling more: seeing friends we hadn’t been able to see living states apart the years prior.

During our week near Raleigh (we actually stayed in Wake Forest- in a short-term rental directly above the candy shop pictured in the first photo below!!), we met up with friends, went to a hockey game with more friends, enjoyed nearby restaurants and breweries, and explored a nearby park.

*We were new to traveling and had no idea we’d ever want to share our travels, so we can’t even tell you the location of the fourth photo below. We didn’t take any pictures of signs, and we didn’t plan our trips as we do now with the names and locations of things we want to do. So if you recognize the location in the fourth photo, please let us know in the comments!

Stop #2: Asheville, North Carolina

Asheville, North Carolina had been on our list for a while as a place we wanted to visit. We thought we’d enjoy all the hikes in the area, and the cideries! 🍻

So after our week in Raleigh, we packed up and headed to Asheville. We stayed in a rental outside the city, continuing our experiment: work during the weekdays and explore in the evenings and weekends.

Since it was the middle of November, it was a little bit more difficult to explore after work (since the sun was setting early), but we were still able to enjoy a few hikes after work and on weekends, and taste-test at a few cideries, too.

Where to next?

We loved exploring! As we worked from hotels and short-term rentals, adventuring on the evenings and weekends, we started to figure out what worked for us. We realized we really enjoyed being on the road and seeing new places.

So, we took things up a level and decided to experiment with one full year of traveling to see how we’d enjoy a full-time “digital nomad” lifestyle.

See our 2020 Travels (including what we planned, how we pivoted when things changed, and our spontaneous 6-week road trip through New Mexico) here.

Your turn! What’s your favorite road trip or the next on your list?

We’re always looking for inspiration, and would love to hear about your adventures too! What’s the best road trip you’ve ever taken (and why), or what’s an upcoming trip you can’t wait to schedule? Please share with us in the comments below!