Sift Voices
December 20, 2022

Tips for a Fun First Digital Nomad Road Trip to Tennessee, Kentucky, Ohio and Beyond

For many, this new world of working remotely has opened up endless possibilities for the travel-minded. Digital nomads each have their own reason for traveling: seeing new places, meeting like-minded people, learning a new language… the list goes on.

With my apartment lease coming up, uncertainty of where I wanted to live long-term, plans to visit family overseas, and a major desire to travel again following the pandemic, the stars aligned for me to embark on my own digital nomad journey. So, I decided to put most of my belongings in storage and hit the road.

Along the almost 1,500-mile journey, I met some cool people, hiked incredible spots, and visited this obscenely humongous gas station/convenience store/jerky shop (I’m sure some know exactly what I’m talking about) – all while keeping to my work commitments and my team.

These are the top things I found helped make my digital nomad road trip more enjoyable. I hope this post inspires you to get out there!

Planning is everything

This is probably the most important factor when deciding to do a digital nomad trek in your car. Yes, it’s cool to see all these places and experience all these things, but if you don’t have a plan (even a loose one), it’s easy for things to go awry and ruin your whole time.

For my excursion, I decided to pick somewhere I could drive from my home base in Detroit. That way I could load my car up with necessities and also see more cities along the way.

My requirements checklist:

  • See multiple cities
  • No more than a 9-hour drive between destinations
  • Stick to budget
  • Good hiking spots with hills
  • Get back by Thanksgiving to see family

With my requirements set, I had a framework I could work with. I always wanted to go to Nashville, so I started with that as my first destination, which is about an 8-hour drive. It’s important to know your own limits. I had previously driven across the country from LA to Detroit, so I knew that driving solo, my limit was around 9 hours.

In my requirements, I also knew I was going to be climbing a mountain in Malaysia with my cousin in December. And if you are from Michigan you’ll know there are just no hills here, so I was in desperate need to prepare myself by doing more strenuous hikes with elevation changes. So naturally, a trip to the Great Smoky Mountains made a ton of sense if I was already in Tennessee.

An added bonus was it was close to Knoxville, where one of my friends lives. One thing I had to plan for was that I needed to get back in time for Thanksgiving with my family in Detroit, so I had to eventually work my way back up north. I searched for cities on the way up and Louisville stuck out, as did Cincinnati. Bourbon, bats, and chili? Yeah, that sounds good to me.

The route I would take. Funny, looks like a bell dangling on a string or something. Right in time for the holidays

Staying in budget

Cook when you can

Naturally, when you are in new places you want to experience everything it has to offer. This can lead to some big-time overspending, especially if you are eating out a lot. Don’t get me wrong, sampling local food is one of my favorite things to do, but when you are a digital nomad you are not on a vacation, this is your everyday life. Spending wisely is critical and that’s why I recommend the following.

I brought a lot of stuff with me along the way and for breakfast, I had a canister of oatmeal, peanut butter, sliced almonds, and dried cranberries that I threw together. For lunch, I would stick to simple meals of sardines, rice, and salads. I would cook enough chicken to throw in a salad for the next couple of days. All very basic stuff that did not take a long time to prepare. 

That is the other thing: you are on this trip to enjoy it and see things – you don’t want to spend all your time cooking! Find something simple you can prepare and eat and go for it.

My go-to staples for breakfast and lunch.

I usually reserved dinners for going out in each city. This worked well, as I had more time after the workday to enjoy a nice meal.

This was not made at home. Pulled pork nachos at Edley's Bar-B-Que along with banana pudding and green beans. 😋

If you are staying in Nashville I would also recommend going to the Food Assembly Hall. It’s a great spot to grab food before or after a Predators game, or a concert at the Ryman Auditorium.

Stay nearby grocery and produce stores

Obviously, you can’t bring everything with you in your car and you’ll need to buy some food. If you live closer, say walking distance, to a grocery store you are more likely to go there. When I stayed in East Nashville I made sure I was close to one. I lucked out and was close to an Aldi, Kroger, and Publix all within a mile.

Get to work

Remember, this isn’t a vacation, so you are going to have to not only keep to your work commitments but excel, all while in a new environment. Here are a few things to keep in mind for creating the most productive work environment for you while on the go.

1. Have a dedicated workspace

When looking at hotels and Airbnbs, check if there is a dedicated work desk or area you can use, especially for taller folks over 6 feet tall. There’s nothing worse than working hunched over a kitchen table, or worse yet, a saggy couch. I might also recommend lugging an additional monitor with you if you can. Definitely bring a laptop stand and external keyboard and mouse – I did not bring mine with me and my neck wasn’t liking me after.

Look for a ‘Dedicated Workspace’ listing on Airbnb near the top and check under the Amenities to see if it is listed.

2. Check internet speeds

Not sure about you, but we can have quite a few virtual meetings at Sift. Being able to come in loud and clear is critical when collaborating with others and nothing kills that more than a spotty internet connection.

Luckily on Airbnb you can search reviews and see how others have commented on the internet speeds. You can also check the Amenities section to see if the Wi-Fi speed is listed. I always made sure to check beforehand at all the places I stayed.

3. Join a coworking space

When I visited my friend in Knoxville, I needed a spot with a good internet connection and where I could get some heads-down work done. I found this place called CoKno. It was a really nice spot with dedicated booths if you needed to take private calls. The best thing was that I met some other friendly people and was able to grab lunch with them to hear more about what they were working on, how they liked Knoxville, and recommendations for places to go. I even found out that Knoxville hosted a World’s Fair in the 80s.

You can’t replace human interaction, and being on the go as digital nomads can make it difficult to connect with people and increase feelings of isolation. More so perhaps when traveling internationally with language barriers, but even within the same country, it’s always good to meet new people. Coworking spaces provide those opportunities, so I would highly recommend checking one out.

4. Navigating checkout times and finding impromptu working spots 

Many places you stay will have you check out around 11 am. The problem with that is for most of us, work doesn’t stop at 11 am. It’s a good idea if you can ask if you can checkout later, but sometimes that is not always possible. In those situations, look into working from coffee shops or coworking spots, as I mentioned above.

One coffee shop I worked from in East Nashville called Barista Parlor (shout out to my friend who recommended it!). It had a very wide open setup with nice long tables along the walls and music that wasn’t too loud but added to the ambiance. It was perfect for working for a few hours after I checked out.

Pretty good coffee and not a bad spot to get some work done.

Again, look into how good internet connections can be at coffee shops. You might be able to search Yelp and get reviews before stopping in. In a pinch, I have used my phone as a mobile hotspot for calls. But be forewarned: one 30-minute video conference took nearly half a gig of data. This might be fine for some people with more flexible plans, but it’s definitely not a long-term solution, so use this as a last resort.

Look over your health and stay active

Regardless of how short or long your stay is in a specific spot, getting exercise in isn’t usually at the front of many’s minds. But it definitely should be, and here is how I was able to work out while on the go.

1. Find a gym 

Many accommodations have a gym attached to them. Hotels will typically have them, and guess what? Nobody uses them. If there isn’t one available, another good thing to use is your gym membership. Many of the larger gyms (like Anytime Fitness, LA Fitness, Planet Fitness, etc.) have locations in multiple states and even in other countries.

In Nashville, there wasn’t a gym I was a member of nearby, so I joined a local gym called Gym 5 for a week. It was within walking distance of where I lived and even though I only got in a few times, it was still worth it to get the blood flowing and clear my head. Many gyms offer day/week/month passes, so ask around.

When I was in Kentucky, I was able to utilize the same LA Fitness/eSporta Fitness membership I already had. I’ve probably been to about 17 different LA Fitnesses across the country and actually get a kick out of comparing different facilities. The one in Louisville was one of the nicer ones I’ve been to with a ton of equipment and even an indoor track.

You can hear me internally debating inside the car if I actually wanted to venture out into the cold on a wet 38-degree day.

2. Hit the outdoors

You don’t need equipment to run or hike. One of the reasons why I wanted to go on this journey in the first place was for hiking. Not only can you get some great exercise from hiking, but it is also a fantastic way to unwind and help with your mental well-being. Here are some of the places I hiked in Tennessee.

Fall Creek Falls State Park (Spencer, TN) 

Situated between Nashville and Gatlinburg, Falls Creek Falls is one of Tennessee’s largest and most visited state parks due to its beautiful waterfalls. The largest is 256 feet and one of the largest free-fall waterfalls east of the Mississippi.

Fall Creek Falls overlook during the rain. I imagine in the spring there is a lot more water flowing down

The hike to the base of the trail gives you an amazing view from the bottom of the falls. About a 0.8-mile out-and-back hike to the base of the falls, with about 280 feet elevation change. If it wasn’t pouring buckets, I’d say it would be a super easy hike, but the slickness of the rocks made it a little more challenging.

In spring and summer time you can find people swimming and gathering underneath the falls. Not on a 40-degree day with rain, though.

The other hike I really enjoyed was the Woodland Trail leading up to Cane Creek Falls. This was about 0.8 miles from the Fall Creek Falls overlook. What makes this falls interesting is the fact that it’s the largest by volume of all the waterfalls in Fall Creek Falls State Park. You also get to cross a swinging suspension bridge.

Cane Creek Falls is located in Fall Creek Falls State Park.

Great Smoky Mountains National Park

What else is there to say? One of the most famous parks and home to some of the highest mountains in the eastern part of the U.S. The Smokies was one area I came to with a clear purpose of getting in some training for a future mountain climb.

A old abandoned cabin in the woods in Gatlinburg

The Gatlinburg Trail is a great intro hike that is right in town and takes you along Little Pigeon River. It’s about 4 miles out and back. Like I said, it’s a nice little warmup hike that is pretty flat.

Nice Fall day in Gatlinburg along the Little Pigeon River

The Cade Cove Mountain Trail is a great training hike for aspiring mountain climbers, and once you get about 3-4 miles in you will hardly come across anyone on the trail. It can definitely be mentally challenging, as there are no tremendous views to be rewarded with and you are pretty much blocked in by trees. With all the switchbacks, at times it can make it seem like you are hiking through the same part you just came from.

Can get very delirious hiking hours and hours and seeing much of the same terrain

I got about halfway and with all the rain and getting a bit of a late start, I only hiked about 6 miles in – all the way to about 3,000 feet in elevation to a spot called Mt. Holy Butt. Yes, I’m not making that up. After that, I decided to head all the way back home and call it a day.

My feet were not liking me one bit, especially after hiking the previous day. It never felt better to take a shower and hit the couch!

Mother nature doesn’t care about your plans

My last day in Gatlinburg was a little disappointing, as the weather had other ideas with snow in the mountains. I wanted to hike Mt. LeConte or Chimney Tops, two of the more popular hikes. But since I always like to leave something for the next time I visit a place,  these two hikes would have to wait. Besides, it could have been a good thing with how tired I was from hiking more than my body was used to the previous two days. As a nice farewell, I was greeted with a nice view on my way out with some beautiful snow-capped mountains.

Caught an early morning snow covering the tops of the Great Smoky Mountains as I left Gatlinburg

Look over yourself, have some fun, and leave something to come back for

Remember, even though you’re working while doing so, the reason you are traveling is to have fun. Do things you enjoy and see what you want to see. But also don’t overdo it. As I mentioned with the hikes, I always like to leave something for when I return in the future. When you are stringing along multiple cities road trip style, it becomes even more important to pace yourself and take more time since you will be driving, on the go more, and more prone to being tired. You don’t want to rush things so much to the point where you can’t take in new views and experiences. Here are some of the ways I had a great time during my road trip.

Discovering Country Music

During my one-week stay in Nashville, I really wanted to check out the music scene. After all, it is “Music City” and I love going to concerts. I will say I was not a diehard country music fan before visiting Nashville, but it certainly rubbed off on me and I find myself listening to The Highway or Y2Country on SiriusXM a lot more often.

A shot down Broadway. So many bars and live music spots at every stop!

Ryman Auditorium and the Grand Ole Opry

I was fortunate to see a concert at the hallowed Ryman Auditorium, which is basically the spot that popularized country music and made it into what it is today. The place was host of the famous Grand Ole Opry live radio broadcast in the 1920s, and having that history of knowing how many famous musicians played there was really moving.

The Ryan Auditorium at Night

Alas, not all music in Nashville is country, and I ended up seeing The Revivalists, a rock band from Louisiana. I’ve only heard one of their songs before called Wish I Knew You, but I got to say they gave a great live performance full of energy and love the combination of pedal steel guitar and saxophone that really filled the auditorium with a concoction of bluesy rock.

The Revivalists perform at the Ryman Auditorium

The Grand Ole Opry was something I went to on a whim. I wanted a traditional country music experience and this 100% fit the bill. The cool thing about the show is it is eight different acts and the set changes between acts is incredibly fast. What I liked the most is they have a very diverse mix of talent, from old school legends to more recent headliner acts. In fact, there was even a hilarious comedian Henry Cho, whom I had never heard of before, but wow was he funny! He spoke a lot about growing up being Asian in the south, and being half Asian, I could actually relate to some of the things he was saying. It was a nice surprise.

The lineup for the night I attended included Lee Brice, Nitty Gritty Dirt Band, Rhonda Vincent, Maggie Rose, and more.

It was great to get some feel for country music and listen to everything from bluegrass to modern country. I can’t recommend enough checking out a performance at the Grand Ole Opry. The fact that is a live radio show is really cool as well and adds to the experience.

Lucky to see Lee Brice and several other country music stars

Bourbon and bats in Louisville

As I worked my way back up north, a stop in Louisville was a must. I’m a big baseball fan so the Louisville Slugger museum was can’t-miss. In addition, I’ve always heard about the Bourbon Trail and wanted to see – or rather, taste – it for myself.

I decided to go on one tour at the Old Forester distillery right on Whiskey Row in downtown Louisville. It’s an incredibly clean and modern-looking facility, and the tour was a must in my opinion. Even if you are not into bourbon, or don’t even drink, the amount of history I was able to absorb during the tour was worth it by itself. I was able to learn how distilleries like Old Forester were still legally able to bottle bourbon and sell it during the prohibition since it was “medicinal”.

Barrels on barrels at the Old Forester Distillery in Louisville, KY

Also got to see how they made their barrels. The part where they showed how to char the inside of the barrels with a flame was something else. And I had no idea how much of a process it was going through all of that.

Now time for the tastings! A tasting is included at the end of the Old Forrester tour and they had us try the 100 Proof, Statesman (made for the Kingsman movie specifically), Bottled in Bond, and Prohibition Style. It was a toss-up between the Bottled in Bond and Prohibition Style for me. I’m not going to tell you I could taste notes of this or that, I’ve honestly tried bourbon a handful of times in my life and am by no means a connoisseur.

I also went to Peerless and did a tasting there. I tried their Single Barrel, Single Barrel Blood Orange Selection, Rye, and Double Rye Speakeasy, and got a bonus pour of the Rum Barrel version too! I definitely liked the Single Barrel selection the most. It was aged in a specific barrel that gave it hints of citrus bitters, cinnamon, and toasted sugar. It was almost like drinking an Old Fashioned.

Great bourbon tasting at the Peerless Distillery in Louisville, KY

I saved the bats for last with a stop at the Louisville Slugger Museum and was greeted by a gigantic bat right outside the museum. What I never realized was how customized the bats are to the specific players’ preferences. I always thought it was just a piece of wood and standardized across the board. But the tour guide let us know that certain players had different ends of the bat and some players would have the bats go through extra durability/rolling tests to make them more solid and less prone to breaking. You also get a chance to hold some of these bats that the players eventually would. Pretty cool feeling holding the bat that Vlad Guerrero, Jr. may some day hit a HR with!

Actual future MLB game bats before they get finished at the Louisville Slugger Factory Tour

Surprising Cincinnati

Cincinnati was the last stop on the way, and I’ve got to say that it really surprised me. For one, I never knew Cincinnati was right across the river from northern Kentucky and you could walk the bridge right across (pretty cool)! I’m a sucker for bridges.

A look at the Cincinatti Skyline

Another pretty neat thing, I was impressed with the amount of murals Cincinnati has: over 20,000, and it is ranked the #2 best city for street murals.

Still trying to figure out info on this mural by Findlay Market and Rhinegeist Brewery at the corner of Findlay and Elm. Beautifully well-done and lifelike.

Findlay Market is one of the must-visit spots in Cincinnati. It’s full of vendors selling meat, produce, and  other local foods. There is also an above-ground light rail station that passes by. 

I stopped by a place called the Arepa Place. Fittingly, I ordered a stuffed chicken arepa, which is a food typically found in Colombia and Venezuela. It contains fried ground maize dough filled with mozzarella cheese, black beans, and chicken, although you can also get beef, chorizo or plantains. Muy sabrosa!

Another day, I stopped by an Argentine restaurant called Ché. It was a place known for its empanadas. I ended up going during brunch and had something called “adios rescaca” (“goodbye hangover”).

Two sausage, egg, and cheese empanadas. Breakfast tots, chorizo and goetta gravy. Top with chimichurri, an egg, and melted provolone. It’s a good thing I was walking a lot!

The bartender was also really cool and I noticed he was wearing a Rhinegeist Brewery shirt. I never tried their beer but heard a lot about it. He recommended I check out the brewery and try their seasonal beers. What an awesome taproom: wide-open, and in a historic bottling plant! hey had tons of games and were hosting an event called INKED. For the event, they had a limited release of their inky dark Imperial Stout and on top of that, they were doing live tattoos of pre-selected flash art on the spot.

What else is there to say? Taking a digital nomad road trip, even if it’s not one to an exotic, warm place like Costa Rica, can still be a ton of fun. I hope you are starting to plan your trip (wherever it may be). Stay tuned for additional posts from me as I continue my digital nomad journey overseas. I’ll be visiting Asia and stopping by places like Japan, Malaysia, Singapore, and Australia.

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