Working Remotely in Rome, Italy

Touring the Underground of the Colosseum

This is part of mThis is part of my remote work travel series where I review places I visit as a digital nomad. Check out the rest of my posts and follow me on Instagram, YouTube, Substack, or on TikTok for more travel content!

I, like everyone else in my generation, grew up watching Lizzie McGuire run around Rome with some Italian superstar and have a wholesome adventure around all of Rome’s major landmarks. Move aside, Roman Holiday, there’s only room for one legendary pop culture reference in this blog post.

We spent two weeks in Rome living and working remotely, and it was by far one of the most beautiful cities we’ve stayed in on our trip.

Rome is also where I launched my new course (!!!) breaking down how the heck I earned $300,000+ on Upwork as a freelance writer, and tips and tricks for all creatives and digital nomads who want to use the platform to scale whatever digital hustle you’re running. I’m rooting for you, friends! Keep me posted on what kinds of content will be helpful for you on your journey. I like teaching almost as I like fancy espresso served in tiny, tiny cups.

OK, back to our regularly scheduled Trevi Fountain content:

Living in Rome, Italy as a Digital Nomad

When I say Rome is breathtaking, I mean that every time you turn a corner you’re hit with a building older than your imagination and more stunning than you’re prepare to observe with your human eyes. I was gasping at every boulevard as we dipped into chapels and even historic-feeling boba shops. (Yes, there are boba shops in Rome.)

Rome is also Tourist City. This is new to us on our trip: we mostly have inhabited small towns on our roadtrip and in Europe have been to lovely but tourist-lite cities like Prague and Budapest. Rome? It was veritably poppin’ off with people. On the Friday night we arrived, people were chillin’ on old stone steps drinking a cold one with the boys. (And by “Boys” I mean the ghosts of Michaelangelo and Raphael, obviously. Rome must be haunted AF.)

With tourist attractions comes Tourist Prices. In Prague and Budapest, we were maybe spending $50 USD per day on food for 3 good restaurant meals for two people. (Seriously… Eastern Europe is as cushy as it gets when you factor in conversion rates.) In Rome? Two meals for two people per day were about $100 USD. Definitely closer to what you’d pay in LA, and so for that I mourn the weeks we were riding high on favorable currency exchanges. Enjoy it while it lasts, friends, and get into Bitcoin. (I’ll save my Crypto predictions for another post.)

When in Rome, it’s easy to walk slower, peruse local shops, and participate in the nap-at-3pm-and-eat-pasta-until-midnight culture. “Hustle culture” Rome is not. It was a nice change to the bustling cities we’ve been to recently (I’m looking at you Naples and NYC) but I don’t know if I could live here long term unless I was ready to shed all of my worldly belongings at the alter of the Buffalo Mozzarella gods. (Don’t tempt me…)

Anyways, I’d give Rome a solid 5/10 for a digital nomad’s stop: beautiful city, lovely humans, good food, but not as cost-effective and honestly (and don’t smite me when I write this) Prague had better food. There’s also no laptop-friendly coffeeshops or places to work, and no WeWorks in this city because that’s not the vibe, so don’t expect it to be a place you’re hyper-productive. It’s more of a stop-over where you can get into a pasta coma and see some incredible historical landmarks.

RELATED: The Best Travel Cards for Digital Nomads

Best Things to Eat in Rome, Italy

Being mostly vegan in Italy is not impossible, but it’s definitely not easy. Our favorite vegan-friendly spots were Buddy Vegan (our favorite), Ginger, and Escosazio. All three of those spots are great breakfast stops. Buddy Vegan in particular had an awesome breakfast/brunch menu.

If you’re not vegan, you can mostly just roll the dice and stop into most pizza and pasta places for a solid meal. We stopped at Pizza Florida for thick-crust slices that were heaven in a bready pizza slice. The best pizza we had in Rome was O’Pazzariello’s four-cheese pizza.

We also loved Roscioli, a Michelin-star restaurant with the best focaccia bread I’ve ever had…. ever.

We also had a dreamy night where we walked past string-light laden streets on our way to dinner at Dilla, which had amazing pasta. On our way, there were street musicians playing gorgeous violin pieces that echoed all around the evening streets of Rome, a crowd forming to watch.

What to Do in Rome, Italy for Digital Nomads

The nice thing about being in Rome for an extended amount of time is that you don’t need to rush around and hit all of the landmarks in one day. We toured the underground of the Colosseum which has just opened to the public, and it was very cool. We learned some interesting things from our guide that shattered our illusions of what gladiators were like. Move aside, Russell Crowe: most gladiators actually were overweight because they didn’t actually fight to the death, they fought to first blood — and the more body fat you had, the more likely it was that you wouldn’t get speared in a vital organ.

We also saw Vatican City and the Sistine Chapel, and if you’re a fan of art or just a human being on planet earth, I highly recommend going. The Sistine Chapel is very strict with its dress code (no bare shoulders or knees!) and you have to be completely silent when you’re observing the chapel.

However, our favorite experience in Rome was sketching and painting with a local artist. It was an Airbnb Experience, (of which we’ve done a ton of!) and it was so lovely to see the city in a new light as we tried to translate it onto our sketchbooks.

Work/Life Balance & Dealing with Bad Days as a Digital Nomad

I’m currently writing this from our apartment in Milan and home from the next two weeks. It’s a Saturday night and thunderstorms are a-brewin’ on the horizon. This week has been hectic because it’s been a meeting-packed week — and a travel week, as we made our way from Rome to Milan on a stressful train trip on Wednesday.

This morning Kyle and I were planning for a very chill day of resting and started the day with some yoga and a slow wake-up. But by the time we left, all the breakfast spots we went to were busy/only taking reservations and booked out until October. Then I had to deal with a one of those nightmare freelance clients who was just one of those hurt people who enjoys hurting other people, and the weight of this week just felt really heavy. After an hour of trying to find some breakfast, we got a very sad cold veggie bowl at a local restaurant, and my mood was just not great.

That’s the part of being a digital nomad you don’t see: the struggles of being in new cities every two weeks and not having your “brunch spot” or even know where in the city to get contact solution. Or dealing with bad clients and busy weeks that feel overwhelming on top of trying to get from one train station to the next.

But things can be hard from anywhere: it’s hard staying in one city and not seeing the world. It’s hard to be in a monotonous routine. We all choose our “hard” in a way that shows what we prioritize and what we’re made of. I’ve dealt with bad clients and work experiences from LA to Milan and beyond — there are going to be bumps in the road that are inevitable, you just need to keep on moving.

I’ll share some more tips as I continue to find better “best practices” to manage everything, but sometimes you just have bad days. Sometimes you feel a bit beat up and just feel sad.

A lot of stoic/yogic philosophy can be read as: “don’t get attached to bad days! Just let it all flow and let go.” And while I agree with that in part, I think we also need to honor and make space for negative emotions to flow through us rather than just trying to rush them out of our system or repress them.

Our day ended up turning around: we took a cooking class that’s one of the highest-rated in Milan, and a wonderful older Italian woman taught us the secrets of tiramisu gelato and making pasta from scratch. We met six people from Israel, Switzerland, Turkey, and America, and shared a meal we all made together.

We ended our day on a high note: running through the streets of Milan as the thunderstorm threatened to blanket the city in rain.

I say let the good and bad wash over you: they’re both part of this journey we’re on, and we’re lucky to be experiencing either set of emotions.

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