Many people dream of being a true Digital Nomad: working from beaches, taking a meeting, and relaxing poolside while writing up a email.
But the reality is there are few jobs that allow for true flexibility post pandemic. Add in those of us who have other things that keep us rooted (ie: kids, spouses) and the life of a digital nomad feels unattainable.
And – that’s true. However, this year I experimented with my company’s “work from anywhere” policy which allows up to four weeks where our in-office policy is lifted. Most people use it to avoid December. But I decided to try something a little different. I did two separete weeks solo traveling Europe – exploring by day, and working in the evening (keeping my normal CST hours).
It’s a way to get a taste of digital nomad life – while also only being away from home, kids, and responsibilities for a week. For me, it was a win/win. I chose Italy for my first foray into this plan and it worked out spledidly.
Day 1: Arrival
One of my biggest travel tips is to do as much distance as possible on the first day. No matter how “nice” the plane ride is, I always find it draining and the first day tends to be wilted. So, just keep going and get as far along as possible.
I took a late flight out on a Friday so I didn’t have to take a vacation day and arrived about midday on Saturday to Naples. I immediately grabbed the bus to Sorrento. Though I’m usually a train girly, I highly recommend this strategy. The bus was easy and straight forward.
Because I knew I was going to be spending the majority of my evenings working, I opted for a really comfortable airbnb in a smaller town. My goal was to get that lived-in feel and not feel pressured to see every nook and cranny of a larger city in my limited time.
I chose The Lookout of Pipiano which is in Massa Lubrense, a town west of Sorrento. It was a dream spot with an exceptional host, Caterina, who helped me book outings. She also arranged to pick me up in Sorrento.
I’m a huge fan of this airbnb and little town and would highly recommend it if you are coming to this very touristy Amalfi coast are of Italy. This town still feels local and quiet. While I liked Sorrento as well, if you are looking for beauty, quiety, and vibes while still having excellent access, this town, and particularly this airbnb, is a gem.
Once I was settled in the airbnb, I took the 5 minute walk town to the port and went to Angelo’s for dinner. This restaurant became my hangout for the week. The food was the best I had all trip, the view of the dock and sunset was to die for, and the staff was so sweet to me. It’s easily the thing I miss the most from my whole trip.
Day 2: Amalfi Coast Boat Tour
Being a Sunday, I made sure to do one of the more full-day activities I wanted to do. Caterina had provided a whole list of options when I booked the airbnb and I eagerly took her up on it. This is key because while there were very similar tours listed on places like GetYourGuide (which I do love, btw), having Caterina arrange meant that I was able to get picked up at the local Massa Lubrense dock and didn’t need to get a ride or 40 minute bus into Sorrento.
The biggest decision had been to do either Capri or a boat ride down the Amalfi Coast- it was tough but I opted for the coast and took a tour very similar to this one – where we stopped at Amalfi and Positano and I really enjoyed it.
The boat left the dock at 9am. It took a good hour or so to go down the coast. It was actually choppier than I expected, given how close we were to the shore, but nothing my nausea pills/patches couldn’t handle. We stopped at Amalfi first and, while beautiful, it wasn’t my overall vibe.
With one long main road it’s absolutley packed with tourists and tourist catered stores. Lots of fun knick-knacks to shop for, but towns like that always make me a bit sad – it’s lost so much of it’s original charm.
That being said, I did locate a pizza place, Pizzeria Donna Stella, that was tucked away in a courtyard with lemon trees that was very cute. For me the pizza was only okay, but it was worth it for the vibes and plenty of seating. At the end of the tourist street I took a break – it was so hot – and grabbed a cappuchino and lemon cake that was exceptional at Bar Della Valle.
Then it was back to the boat and further down the coast to Positano. I liked the town of Positano much more, as a lot of the space to explore is more spread out and built steeply into the cliffside. It reminded me of the towns on Lake Atitlan in Guatemala.
Absolutely beautiful but also brutal to explore. I was sweating profusely and fighting for my life to climb to places that looked open on Google maps only to find they weren’t (I blame that it was Sunday).
Still – the views were great and I did soothe myself with gelato from the appropriatley named Yummy and later a limoncello spritzer from Sole where they had a nice patio for people watching.
All in all, the times in town were decent especially if you are like me and quickly get overwhelmed by tourists and touristy things. The boat and sunshine of the ride was lovely. Definitely a day trip worth taking in the area.
Day 3: Exploring Sorrento
Monday morning rolled around. The whole plan was to spend the day exploring and then work Chicago time in the evening. When it’s 3pm in Italy, it’s 8am in Chicago. I decided I would do some of my own exploration on this first working day. I walked up the steep but simple path to the main town of Massa Lubrense, grabbed a coffee at Bar Dolcevi, and easily caught the bus into Sorrento.
I had hoped to do a walking tour but apparently I was the only one who signed up so the tour ended up being cancelled. So instead I just wandered up and down the main streets of Sorrento. While I didn’t learn much, it was actually nice. There are a couple main streets with lots of shops and food.
It’s also nice to walk all the way to the cliffside to look out over the water and the unique beach club where you can actually take an elevator down to the water (which I did not do). Sorrento was really pretty to me and, if I needed to come back but be in a larger area, it’s for sure where I would stay.
I did hit a snafu on my return bus. I completely missed my stop for home. I hadn’t realized that, even though I was on the right numbered line, they had different routes and the road that led to my airbnb was completely skipped.
It ended up being pretty funny. I was the only person on the bus and took a very scenic ride all around the peninsula and all the way down to Marina del Cantone.
The roads were steep and narrow and it was like being on an amusement park ride. The bus driver kept looking in the mirror and was clearly concerned. But, with no real language in common, I just shrugged, said I was fine, and kept riding until we came to a larger town where I felt certain I’d be able to find my way back.
That ended up being Sant Agata sui Due Golfi. After identifying when the next bus should be, I made the most of the stop and grabbed lunch at Racy which had a lovely lemon pasta special. The town looked cute but by then it was just after 2 and I had to get back for work. So it was back on the bus and it took me cleanly to Massa Lubrense. I was home about ten minutes before my first work meeting.
Day 4: Lemon Farm
Working until midnight Italy time (5pm Chicago time) and then getting up early enough the next day is a bit rough but doable for just a week. On Tuesday I reserved a day trip to a local lemon farm, La Masseria. I booked mine through Caterina so they picked me up in Massa Lubrense but this tour is almost certainly the same thing.
I really enjoyed this experience. It’s family run, 4th generation, and a beautiful space. They walk you through the vibrant lemon trees, offer photo ops, and unique information. I learned that that Sorrento lemon trees can’t be grown from seeds, but are instead spliced. It was the perfect amount of information with also some other delightful farm details (they also have olive trees, some animals, etc) and tastings. They even did a full, sit down lunch which was tasty and just generally really fun.
It’s simultaneously a well-run operation while also being very small and local. Highly recommend this experience if you are staying in the area. And it ended in the early afternoon which was plenty of time for me to get back to the airbnb and set up for work.
Day 5: Travel Day
Wednesday morning I grabbed the bus early into Sorrento, checking out of the delightful airbnb. It was going to be a travel day to Naples where I planned to stay and work for the remainder of the trip to be well positioned for the airport.
The bus outside my airbnb took me up the hill where I tranferred to the bus to Sorrento. There I opted for trying the train to Naples. I had heard mixed reviews on the train and I understand why – for the distance to Naples, it felt more like a subway style train than a regional one. But it was easy and I was able to get into Naples without confusion.
I opted for an airbnb in the old part of the city, what they call the Spanish Quarter. It’s aptly named, it very much reminded me of the Born neighborhood in Barcelona. I stayed here, and thought it was a great spot. It’s fairly bare bones but it’s in a great location, the owner was super kind, and I’m a sucker for a balcony.
Once I dropped my bags I took to the streets for some general exploration. This tends to be a polarizing city and I unfortunately am siding with the haters. Naples is one of the few places I’ve traveled that I truly disliked. Some people love it and, to each their own, but I was not a fan. The energy reminded me of a low-budget tourist experience. Tourists walked around exhausted and cranky, like 5pm at Disney World. Meanwhile the locals seemed irritated by everyone, tourists and neighbors alike.
Both the restaurants I went to on this day for lunch and dinner, though rated highly, were very mid experiences so I won’t be listing them. Once I was back to start working, though, I did enjoy being able to sit above the Spanish-style streets in my airbnb, emailing and listening to the bustle below.
Day 6: Pompeii
The main reason why I came to this part of the world was to see Pompeii and my tour day was finally here! From my airbnb I took the subway back toward the main train terminal and walked a number of very chaotic streets to find the pick up location.
I booked the tour through GetMyGuide. While this was totally fine, I would personally recommend finding something else. Our guide on-site in Pompeii was quite lovely but the pick up experience, van, and overall care put into the experience was lacking. Honestly, though, it very much matched the vibe I got all through Naples.
But back to Pompeii – what a special place to see. The guide took us through a small portion. It’s huge, so there are a variety of lengths of tours you can get through GetYourGuide or others – but I kept it fairly short since it was a work day. We still saw a lot and received plenty of really interesting details. It’s definitely worth a visit.
After Pompeii I had time before work to do a bit more exploration of Naples. I was determined to find a neighborhood I liked, but failed. I took the very old funicular up to the castle and wandered that less touristy area but didn’t see anything differently. I also had a very lackluster pasta experience there as well.
Thankfully, the pizza I had when I was able to sneak away from work for dinner was worthy so if you are in the Spanish Quarter of Naples, Pizzeria Laezza is a solid stop. It’s also fun because you sit in the narrow road with people and scooters zipping by. It was a very Naples experience (in a good way!)
Day 7: Travel Home
Friday morning, I did walk through the Spanish quarter in the morning to find a coffee and chill with my book. It ended up being awkward as it was immediately apparently I had taken some old Italian man’s usual spot. He was in luck, though, as I didn’t linger. It was back to the airbnb to pack, check out, and head to the airport.
All in all, I really loved this mini experiment and was one I quickly realized I would be repeating (stay tuned for my post on the next time I did this, in Spain). While working in the evening really messed with my sleeping habits, it was a really great balance for me. I didn’t have the work stress that inevitably comes when taking time off, but I still got to see and do amazing things.
Doing it solo allowed for a ton of personal flexibility and I never felt guilty dragging a travel buddy back early, nor did I have FOMO about needing to be back in the room while they would still be exploring.
And while Naples was not a place I would ever intentionally go back to myself, I do think this was a great area to do a quick working week – I feel like I was able to see a lot without feeling like I missed out on anything either.
The Roaming Reader 