Life With Landing / Meet Our Members

How We Lived as Domestic Digital Nomads Before Launching Our Adventures Abroad

By Landing | Dec 16, 2022
Landing members Jennifer and Zack

This is a guest post written by Landing member Jennifer M.

For years, my husband Zack and I had the goal of traveling long term, but he needed a location-independent job to support that goal. Because of COVID, Zack’s job became 100% remote, which springboarded this idea that we could now live as snowbirds, spending winters in our Florida home and then traveling and exploring somewhere new the other six months of the year.

This year, we started our journey living with Landing in Chicago from May to November before moving back to our permanent home in Florida. This experience brought us one step closer to our eventual dream: traveling internationally for extended periods of time. 

Here’s how we started as domestic digital nomads to make sure this lifestyle worked for us—and what we’ve learned along the way!

Launching our lifestyle

The longer we’ve lived in Florida, the more appealing the snowbird lifestyle has become. We can’t stand the summer heat anymore, so we anticipate these extended trips will happen yearly. First, we paid off our mortgage, so we have extra savings to pay for rent and give us the financial flexibility to travel. 

While we started living as snowbirds in the U.S., Europe is particularly our passion. I once was a foreign exchange student in Spain for 12 weeks, which was really impactful. While I loved the immersion in another culture, I definitely experienced culture shock. So, this time, we want to delicately step into living abroad rather than jumping in.

There’s a lot of things to consider when living abroad, so we figured our first trip would be easier in the U.S. Next year, we plan on traveling to London since we won’t have a language barrier, making it one step easier. Then, we’re hoping to travel to the Netherlands, Spain, and Switzerland. The list goes on and on, as we plan to travel to a new European country each year! 

We also have a sweet little dog named Aerie, so we wanted to make sure she was comfortable with traveling and being in a new environment. We’ve been training her since puppyhood to travel on any mode of transportation, but our flight to Chicago was her first time on a plane. Luckily, she was totally fine the whole way. 

How we wound up in Chicago

My husband has always wanted to live in a city, but we didn’t want to go somewhere as big as New York. When we were originally making plans, most cities were still shut down because of COVID, so we had limited choices. Austin initially seemed like a good option for us, but more cities started reopening in March, which revised our plans. We had some family in the Chicago area, so we started seriously considering that destination. 

We’re both CPAs, so we’re really big planners—we love spreadsheets! We did a ton of research ahead of time about Chicago, especially around safety, public transit, things to do, etc.

When planning to move to Chicago, we found that renting a short-term, furnished apartment was a little daunting. That’s when we came across Landing’s furnished apartments, which offered us a convenient way to find housing that matched our travel plans. It was nice to have a big portion of the process taken care of for us. 

Our day-to-day life in the Windy City

While we were living in Chicago, we pretty much kept our normal routine during the week just like if we were at home. We took Aerie for lots of walks, so it was nice to get to know the city on foot and feel more like a local than just a tourist. Aerie loved city life with so many people!

On the weekends, we’d go out more than usual. On Friday nights, we’d find a cool speakeasy or cocktail lounge and try some new drinks, and then on Saturdays and Sundays, we’d find a new restaurant to try out. Otherwise, we’d explore the city or find local things to do. We’re also really into Broadway shows, so we went to almost every one of them while in ChiTown.

Over six months, we probably stayed within a two-mile radius from our Landing because we were so centrally located. There was so much to do within walking distance or by jumping on public transit.

We did a lot in Chicago, but we didn’t have to jam everything in because we were there for such an extended time. We pre-planned most outings but also left room for flexibility and spontaneity. Occasionally, we added last-minute things to our itinerary. 

Our advice for other digital nomads

Since we’ve gotten back to Florida, we’ve already identified a couple of things we’ll do differently. For our next trip, we’re going to research the area a little better. Because we’re going to stay for so long, being in a safe, comfortable area is even more important. It’s not as critical if you’re just traveling for a week or two.

Another challenge was figuring out how to pack for six months. We vacuum-sealed our clothes so that we could condense them enough. While we definitely over-packed some things, we also under-packed other things. It’s just a live-and-learn experience to figure out what works, though.

As CPAs, budgeting and planning is of the utmost importance, especially when traveling for so long. Plus, our suburban lifestyle is much cheaper than most cities, so saving ahead of time is critical. Quite a few extra expenses popped up, so we were happy that we had planned ahead. In summary, we’d suggest other nomads to research, budget, and pack wisely! But also, live and learn to find what works for you.


Ted may be the world's slowest typist and struggle to hold a pen, but he has mastered how to pursue a more flexible lifestyle throughout his airborne adventures around the U.S. Whether you're looking for more information before migrating to a new city or want to find an easier way to rent a nest—erm, apartment—Ted will always be here to share his best advice for where to live and how to thrive.