Why we take digital nomads on road trips and make remote work an adventure

Why we take digital nomads on road trips and make remote work an adventure

After two years as a digital nomad, I started to burn out.

I thought that working remotely while exploring the world would be the dream. Until I discovered the downsides. Loneliness, no solid relationships and lack of a higher purpose were eating away at my happiness.

I had been travelling around Europe, south-east Asia and the UK working as a food and travel photographer. Staying in each place for a few weeks.

Until I met Machado, a friend of a friend who was taking remote workers on road trips.

The power of belonging to a digital nomad community

Thankfully, Machado was looking for a partner in crime. He said, “Let’s take remote workers on adventurous road trips.

“Let’s create environments that maximise the potential for deep, long-lasting human connections. And have a ton of fun while doing it.”

After considering it for about half a minute, I said “Hell yes, I’m in.”

Fast forward to 2022, a year after that conversation, we’re running our second adventure with our company, Remote 9: an epic 17-day road trip around Sicily.

On a digital nomad road trip, you can work from anywhere.Giulia Verdinelli Photography

Sicily had the perfect mix of culture, food and adventure for a road trip

We chose Sicily for our co-working road trip because it’s a manageable size and offers incredible food, a chill ‘aperitivo’ lifestyle and rich cultural scene.

We gathered a group of nine digital nomads from Italy, Sweden, Hungary, Ukraine, the Netherlands, the UK and the USA. They worked in everything from sales and digital marketing to social media and content creation.

What they all had in common was working remotely and sharing a passion for adventure and personal and professional growth. They were all missing what I was: deep, long lasting friendships.

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Palermo – A fascinating melting pot where our road trip began

We all met up in Palermo, Sicily’s capital. After a few days getting to know each other, we hired two minivans and set off on our adventure.

Having our own transport gave us the freedom to take the northern coastal route, from Cefalu to Capo d’Orlando. The road runs along cliffs right above the ocean. Vans are also the only way to reach some great places off the beaten track since public transport is not amazing in Sicily.

Why we chose to stay in private houses along the way

We had booked private villas to stay in as a group. We made our choices based on number of bedrooms, surrounding amenities and plenty of space inside and out to work.

We asked our villas in advance for the wifi speed because if there’s one thing that digital nomads can’t put up with it’s patchy or slow wifi.

Despite our forward planning, the wifi still let us down sometimes. We got around this by carrying three routers with different internet providers. These were a lifesaver, especially in more rural areas.

We stayed in private houses along the way.Giulia Verdinelli Photography

Our road trip route around Sicily and how we planned it

I loved planning our road trip because we were spoilt for choice. There’s so much good stuff in Sicily that it was hard to narrow it down.

We spoke to the tourist board who gave us some great insight. Then once we got to a new place, we asked locals for the best spots, fun activities and events.

It was thanks to them that we found the cous cous fest in San Vito Lo Capo, the hidden fish auction in Mazara del Vallo and the best snorkeling spots in Macari beach and at the Zingaro natural reserve.

We stuck to Sicily’s main cities and large towns – Palermo, Catania, Taormina, Siracusa and Trapani.

We wanted to avoid the poor roads and lack of 4G that you often find in rural areas.

Timing is everything on a road trip

We spent between three and five days in each villa before moving on. We tended to stay around the villa during the week while everyone was working, then explore the surrounding area at the weekends.

Our trip lasted 17 days. Why so specific? Well, in Machado’s words, “After two weeks you’re friends, after three weeks you’re family, and after four weeks you hate each other.”

17 days gave us enough time to get an overview of the whole island by hitting all the great spots. Some of our favourites were the salt farms in Trapani, the clear waters of Scopello and hiking up Mt Etna.

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What taking remote workers on a road trip taught us

Running a road trip for digital nomads is by no means an easy task.

Sicily added the extra challenges of unreliable internet, few English speakers and rocky roads that weren’t well-suited to vans.

We learned to have a plan A, B and C for everything. Multiple wifi routers, a variety of places we could co-work from, and an Italian speaker on speed dial.

But the most important lessons we discovered go beyond logistics or locations. They’re about the human condition.

We learned that deepest connections are formed when you go through intense experiences together.

We’ll never forget jumping off a cliff hand in hand in San Vito Lo Capo, climbing Mount Etna at dawn to watch the sunrise, stargazing on the beach in Sciacca, tasting the purest salt in Trapani and the sweetest pistachios in Bronte, brunch on a boat in Scopello and countless ‘aperitivi’ with stunning sunset views. Those moments, happy memories and feelings of gratitude will stay with us forever.

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Something unexpected that made us fall in love with road trips even more is boredom on journeys. Once we’d sung our hearts out to the radio, the conversation would often turn to deep, philosophical topics. We definitely got to know each other better thanks to the luxury of time.

We made the most of the freedom and flexibility that the digital nomad lifestyle gives us while having a blast in good company.

Ultimately, all of these factors boil down to having your cake and eating it too.

You can find out more about Remote9’s road trips here.


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