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How Moving to Italy as Digital Nomads Went Wrong…

How Moving to Italy as Digital Nomads Went Wrong…

Even though I’m European I haven’t lived in continental Europe much as an adult, as I spent most of the time in North America or London, and I really only worked in the Netherlands in Europe. While we can safely assume that I’ve been Americanized to a point, I still wasn’t too bothered by European habits like the lack of dryers or shops and restaurants closing early.

Living in Europe seems cheaper than in the US. In most countries, you can get a bigger apartment and pay less, healthcare is free, and eating out can be done on any budget. At least in theory. Traveling around Europe seems easier too since there are trains, buses and distances are shorter.

Why did our move turn into a disaster? Let’s start from the beginning…

Moving to Italy digital nomads

Living as Digital Nomads

There’s a huge difference between being a digital nomad and actually living somewhere. In this day and age, many people will try to convince you to become digital nomads to chase your dreams and live anywhere. Hubs like Chiang Mai, Playa del Carmen or Bali become epicenters of digital nomads, but frankly not many of those who claim they live there actually do.

Living somewhere requires dealing with bureaucracy in one way or another. There’s no way around it and while you can avoid paying taxes or establishing residencies or correct visas for a while, it’s no way to live long term. Unless obviously, you want to be a beach bum living out of AirBnBs forever.

I quickly realized that living out of a suitcase in an AirBnB in cheap destinations while doing visa runs every month isn’t for me. Not only because it’s exhausting, but it’s also an imitation of an actual life somewhere. Truth to be told most digital nomads prefer to interact with other nomads only and not making local friends.

Every time I moved somewhere I made an effort to learn the language, hang out with locals, actually get a right visa and other necessary paperwork. Not because I wanted to be cool, but because otherwise eventually you’ll stumble upon many issues. Plus, living out of the suitcase only works if you’re a healthy individual without any dependants.

Before Italy I’ve lived in 6 different countries. In some places adapting was easier than in others, but this time things weren’t as simply as just not adapting…

Let’s start the story from the beginning!

Moving from California to Texas

After getting my green card Matt and I lived in California, after a failed experiment of trying to live in Colorado. Colorado was definitely not a place for me, but that’s a topic for a long separate post.

We liked California, don’t get me wrong. Despite Los Angeles being dirty, dry, and the traffic being awful, we had friends there and I could always find myself new activities to do. However, we always knew that staying in Los Angeles permanently wasn’t an option. I cannot imagine raising my kids in LA and buying a house seemed like a ridiculous idea when the crappiest small houses are going for a million dollars these days.

We wanted to give Europe a try.

Right after Matt got his Irish passport we decided to move to Europe for a bit. Since he wanted mountains nearby we only considered places that weren’t flat, so the Netherlands was out of the question. I wasn’t too keen on living in Austria and we heard of potential issues other blogging friends encountered in Germany, so we picked Italy as a base.

I used to study in Florence, visited Italy many times and my language skills are satisfactory to the point that I can get my point across. Plus, it was surely affordable. Not without a reason, there are so many American retirees living in Italy.

While we were originally planning on considering staying in Europe forever, after half a year of living here we know that we won’t be staying long-term. And nope, it isn’t because we don’t like the Italian lifestyle – we like Verona. However, truth to be told, our move turned into a disaster with everything we planned for blowing up in our faces.

First, because our original plan of staying in California a few months past our contract for the house wasn’t possible. It turned out that our landlord was planning on selling the house and actually preferred us to be out even earlier. Since we were still in the process of establishing our businesses and couldn’t leave the US straight away we ended up in Austin, Texas for 3 months before crossing over to Europe.

Why Texas? We needed to be in Austin for other reasons, such as conferences and projects, so if we were to move out of our house in California it seemed easier and cheaper than finding a short-term rental in California.

Austin tx

Moving to Another State While Pregnant

Finding a short-term rental in Austin wasn’t hard at all. I found a well-located apartment building online and we were able to book it beforehand to avoid staying in an AirBnB at first.

However, we needed an unfurnished apartment since all the furnished ones included bills and we would have zero proof of address for most things. After renting a ridiculously overpriced U-Haul (since it was in August when most students were moving) and attaching our jeep to it we took a 3-day drive to Texas.

Why 3 days since Google Maps says it should take 20 hours? Well, two factors: pregnancy and a cat.

Since I was already pregnant during our moving and during the first trimester I basically couldn’t breathe at all, I wasn’t able to drive as I had breathing issues (still waiting to do the much-needed surgery). Plus, we had Poofy with us and while he’s a good travel cat we wanted to give him breaks to stretch his paws.

Both times in LA and Austin we hired people from TaskRabbit to help packing the whole house, so it really was almost a painless process.

We knew that we needed to transfer our Californian health insurance to Texas once we get registered there in case of an emergency. We had very good insurance in LA with Kaiser Permanente. Expensive, but so it any health insurance in the US particularly for self-employed, but good.

Honestly, every time an American friend complains about the US insurance and says that in Europe it’s better, I have to stop myself from making a comment. If you’re healthy then absolutely – health insurance in Europe for European residents is pretty convenient. However, if you need any serious treatment you have to go privately. I remember my friends and family in Europe waiting for a needed surgery for 2 years sometimes because the hospital ran out of limits. 2 freaking years! Quite often to see a specialist I had to wait at least half a year if not longer.

I was never able to get the medication I needed for my psoriasis. I’ve waited years to finally be eligible for the US insurance and had to medicate myself with meds imported from Mexico, but it wasn’t ideal. In the US I was getting my psoriasis medicines without any issues, plus we already did an introductory pregnancy appointment with a nurse at 6 weeks.

However, imagine my surprise when I discovered that we couldn’t change our health insurance to Texas after we moved from California. While it might be different for those who move and have insurance through their company, there were three insurance companies in Austin that offered insurance for self-employed people like us and were willing to accept us based on mid-year relocation. However, here was the issue…

The first insurance was cheap but basically didn’t cover anything: not my psoriasis medicine or pregnancy. The second insurance covered everything BUT pregnancy, and the third insurance offered a deal that they’d cover pregnancy-related appointments and things after we cover the first $10,000 ourselves. Which left us without any options.

Now, I imagine someone will comment that it’s illegal in the US to exclude maternity coverage or other pre-existing conditions. It IS illegal, but insurance companies still imply these rules, especially in Texas.

This is why we kept health insurance in LA and I had to fly for a day for my other pregnancy appointments or to pick up my supply of psoriasis medicine. Going privately in Texas wasn’t an option since most Obgyns we called had no appointments available or required two introductory appointments to even get to an ultrasound, paid separately.

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Since flying to LA was time and money consuming we also found a private 3d Ultrasound in Austin where I ended up doing my gender check and some check-ups.

Sure, they’re not doctors but technicians, but truth to be told it was the best picture of the baby I’ve seen so far.

I was eager to come to Italy since healthcare was supposedly universal and free once you register in their health system… allegedly.


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Storage in NYC

We thought we were going to save money on not hiring an expensive moving company. We weren’t bringing any furniture, so we thought we would fit in 3 suitcases per person by paying for an additional suitcase on the plane. We shipped the remaining boxes to Matt’s parents in NH and planned on storing them in NYC and pick them up sometime later.

Our extensive research we decided to sell the car instead of shipping it to Italy, since registering an American car in Italy can often be a mission impossible. Thinking about it now – thank God we sold the car!

Getting to the East Coast wasn’t an issue at all. In New Hampshire we arranged all the necessary paperwork for Poofy the Cat and we drove to NYC without any issues.

The storage was cheap, easy to book and convenient. We left 4 boxes there, shipped 2 boxes to Italy with a special box company and went to check-in for our flight. Here’s when a lady charged us over $800. It turned out that while in Texas they couldn’t care less for a 3-4 lbs overweight at JFK they cared a lot.

I straight up refused to pay by saying I’d rather wear a few coats on me than pay that much, which turned into an hour-long process of getting a refund with the manager and repacking.

gender reveal with a cat

Moving to Verona, Italy

Our initial move to Italy went smoothly. We had an AirBnB pre-booked for the first month and the apartment we looked at before even coming to Italy turned out to be available.

We knew about all the nuisances like having to rent out a place for 4 years with a 4-6 months notice, 3-month deposit and long waits for registration appointments, but what we didn’t expect was an extremely high agency fee we had to pay to rent the apartment. We had to pay 10% of a yearly rental which came down to about 1,5-month rent which seems to be standard in Italy. Basically, we had to pay 5,5 months of rent before moving in!

Then it came to installing the Internet. We were assured by the landlord and Internet provider, that we can get 1 GB fast connection which we need for work, but after we signed a contract the person who came to install everything started to even doubt if in this building they can install Internet at all, since cables turned out to be too old.

Fortunately and unfortunately at the same time, they managed to set up a connection, but… that’s not even 100 MG promised to everyone and practically it just works in one room. Plus, we can only connect 4 devices, so forget a smart TV, printer, baby monitor, security cam unless we disconnect everything else. Not to mention we still have to pay like for the fast connection.

After our agency registered our contract officially they helped us schedule an appointment at the town hall to register us as residents. Since we’re both European we needed a housing contract, Italian fiscal codes which we got, and proof (such as tax returns) that we make enough money to sustain ourselves in Italy. That was at least in theory.

In reality, the town hall in Verona refused to register us unless we had a job contract in Italy or moved our entire businesses to Italy, which we cannot do or several reasons. While it might work differently in other regions of Italy, in Veneto they told us that we cannot become residents by proving financial stability and even paying some taxes unless the company will be moved. Even as EU citizens we couldn’t be anything else, but practically tourists in Italy.

Edited in October 2019: Basically, we wanted to be legal and pay their taxes, but they refused us. A few months later I actually found out that it wasn’t just us. While living in Verona we met another American couple who also tried to register. While their situation seemed easier at first as they weren’t self-employed and one of them was actually Italian, they got refused by the town hall as well. They were told that because the wife changed her last name and the marriage certificate is from America (so it doesn’t state the new last name) the Embassy would have to issue a statement saying that she’s the same person as she was before, which the Embassy cannot do. They issued her another passport with an annotation of a previous last name and the date it was changed (ironically, she actually kept her maiden name as a middle name which should already tell Italians she is the same person!) and the town hall still refused them. Hence why they’re also not able to become residents in Verona.

Our original plans of potentially buying or leasing a car went through the window and no registration also meant no health insurance.


While I found a good English speaking private doctor for my pregnancy appointments and everyone (including my doctor) assured us that as EU citizens we are entitled to free emergency care and birth in a hospital, without the insurance it meant no psoriasis medicine which I desperately need.

In California, I had to pay $250, 5 times a year for it. Without insurance, I’ll be forced to pay 3000-4000 Euros 5 times a year.
Edited in October 2019: I was actually naive to think that even with insurance I would be prescribed the medicine that I needed. With public insurance or even willingly paying out of pocket no doctor in Italy, Poland or the Netherlands was willing to prescribe it to me. I tried multiple doctors, multiple hospitals, public, private – you name it. The answer was always the same: I could try starting therapy from scratch and maybe in 2 years if I checked myself into a hospital I would get it, but they doubt that. Many private doctors told me I’m wasting my time here and I should go back to the US. Absolutely ridiculous. I ended up flying to Mexico to get it which I wrote about here.

We tried to get private health insurance or expat insurance for Italy. Our efforts turned out to be unsuccessful since all of them rejected me due to my pre-existing conditions (excluding pregnancy since we knew this wouldn’t be covered) and expensive psoriasis medicine. Our only option was to get my medicine by getting the US health insurance again, but mid-year sign up isn’t possible. Basically, we accepted the fact that we got screwed, but here’s when things became even worse.

Despite what my own doctor has told me, what I thought I knew from experience as a European citizen and my Italian friends assured me of, giving birth in Italy was more complicated. When we went for an orientation meeting at the hospital it turned out that somehow in Verona emergencies and ER are covered for Europeans, but only if they’re registered in another country in Europe and have a European Health Card. Which we obviously don’t have since again – our businesses are based out of the US, not Europe and Matt was never even a resident in Ireland.

After we finally got through to a lovely English speaking doctor at the hospital she tried to make things work but told us that labor isn’t going to be free and we’ll receive a bill for an emergency visit.

She naturally had no clue how much would that cost, but after extensive research, it turned out it’s going to be between 2500-7500 Euros, depending on how things go. While it’s still cheaper than giving birth in the US and I was willing to pay for it (I guess it wasn’t a choice, but must), in Italian hospitals you share a room with many people, you don’t get anything included like gown, towels, formula – in some you need to even bring your own fork and knife or bedsheets.

While they have private birth clinics, they’re not really hospitals so in case of any complications they can’t have you and would transfer you to a regular public hospital. Which in my case wasn’t an option either as we already knew I had complications.

The bigger problem arose when I asked what happens in case the baby doesn’t come out until the due date. Since it wouldn’t be an emergency visit, we will need to be in the Italian health system to check on the baby and perform a possible induction or c-section. The same goes for signing up with an anesthesiologist, so even if I wanted to sign up and pay extra for an epidural (as it’s the only painkiller they use in Italy) it wasn’t going to happen. Basically, unless something super dangerous like I’d suddenly start bleeding or my waters broke they cannot technically treat it as an emergency and admit me, paid or unpaid.

Not to mention that we were waiting at the ER for over 6 hours to even get a phone number from someone before I gave up and decided to leave the ER, while still being charged for waiting in the corridor. It wasn’t the best introduction to how things worked or rather didn’t in Italy. The only thing they solved for us in the ER was that they called my doctor and sent us an email that they still don’t know what to do about me.

giving birth in Italy

Last Minute Trip to Poland

Going back to the US to give birth last minute would result in a giant medical bill, who even knows how much. I thought of going to London since I’m still in their health system, but the problem was that due to Brexit traveling with a pet to the UK is basically a mission almost-impossible.

Thankfully, my friend recommended a private hospital in Poland. It was surely cheaper than in the US, I’d have a private room and everything could be taken care of. It was decided – we were going to Poland.

This is when another problem arose: transporting Poofy the cat. I researched EU pet passports a lot and even on the official EU website it says:

As an EU national, you can freely travel with your cat, dog or ferret if it has a European pet passport. This passport is available from any authorised veterinarian and must contain details of a valid anti-rabies vaccination.

However, this quickly turned out not to be true, since Italy wouldn’t issue us a pet passport without residency. Plus, since the cat is from the US his microchip wouldn’t read in Europe and it seemed to be an issue to an Italian veterinary system. While we finally managed to figure out that we can fly with a certificate of good health, we had less than 48h to arrange his certificate and my certificate stating that I’m still good to fly. Surprisingly enough, we managed.

As there were no good flights from Verona or Venice or the airlines wanted us to book non-refundable tickets just to tell us upon arrival whether Poofy can fly or not (looking at you KLM!), we rented a car and drove to Milan for an evening flight with LOT Polish Airlines.

We were forced to pay more for these flights than for a flight to the US, I kid you not, only to find out once we passed through security that the flight is actually canceled. While I wasn’t too surprised since I almost never fly with zero issues, at 39 weeks pregnant there was a possibility that after running around the airport, then waiting for over 3 hours for hotel vouchers and fighting over a shuttle bus to the hotel with a crowd of angry Polish people throwing their suitcases on the driver, I might give birth on the terminal floor.

Most airlines cut you off after 36 weeks pregnant for flying without a doctor’s note, but truth to be told no one was even mildly interested in asking about my pregnancy, let alone the doctor’s note. There was no such thing as priority anything, better seat, skip the line, nada.

That said, we’re in Poland now!

So far my experience at a private hospital in Warsaw has been pleasant. For the first time, someone has asked me what do I want since in Italy they didn’t offer much choice. The doctors and nurses also speak English, so Matt can actually communicate.

After the birth we’ll be going back to Italy until the end of the year (on and off between travels obviously) before embarking on new adventures.
Edited in October 2019: Dylan was born on April 4th via c-section and my experience was excellent. He’s already a well-traveled baby. He’s an expert flier, travels alone with mummy like a champ and visited Mauritius as his first overseas holiday.

There you have the guide on how NOT to move to Italy and how being a digital nomad isn’t always as convenient as it’s portrayed. Despite the disaster, I don’t regret this decision.


Saturday 8th of January 2022

Helpful to read this, and it does sound all very messy and stressful, and realise you were finding things out as you went. I have travelled a lot and know prior legal advice and research is KEY.

I don't understand 2 points though. 1. Why you assumed you would get a European Health card if you weren't resident in a EU country first? Quick research before would have made this very clear immediately. 2. Residency in Italy. Bizarre what you related but I know from Spain and other countries that officials are not reliable in giving correct legal answers. Why did you not contract a lawyer to assist there or even a lawyer to offer advice and facts before you went. While I dislike lawyers they often can assist specially in the south of Europe.

To say the US healthcare system is better is just simply not true.


Saturday 6th of January 2024

This is...almost the exact opposite of my experience with US health care. People who are healthy think it's fine, but not those with health issues. The wait times you list for European countries are similar to my experience in the US. Additionally, pre-ACA it was impossible for some people to get insurance at any cost and without insurance it was often impossible to get care or medicine, even if you could self-pay.

Anna Karsten

Wednesday 12th of January 2022

The US health system depends on what you need. If you're a healthy person without any serious incidents or chronic conditions then it sucks. If you have a moderate chronic condition then yes, US healthcare is expensive. But... if something serious happens - cancer, genetic disease etc then you can basically die in Europe with long wait times and a lack of treatments available. I could name million of situations when you're basically doomed to fundraising for treatment in the US as a European that would have been included in the insurance in the US. So yeah... until something serious happens to you most people say that, but then you realize it's not so simple.

Also, a European Health Card has nothing to do with an emergency because officially... emergencies and birth rights are regardless of the insurance status.


Thursday 28th of January 2021


I would be curious to find out what you didn't like about Colorado. My wife and I are considering moving there this spring and would be interested to hear if it is more of a personal taste thing, or if you experienced difficulties.

Anna Karsten

Thursday 28th of January 2021

I think it depends on what kind of person you are and what do you want from a place. We wanted a combination between the city and outdoor stuff and thought Colorado would have it. We tried Boulder and it was just awful. It was a crowd of college students, mixed with wannabe outdoor and start-up hippie people (pretty wealthy, so the town was overpriced and everyone had the newest gear from REI, yet they couldn't even make it well on a flat trail despite their gear - quite comical if I'm honest). Tried Denver, but it just wasn't my city I'd say and definitely couldn't find like-minded people. But that wasn't even it - all the outdoor spots were super crowded. National Parks were way too packed after 9am, like worse than Zion. It was crazy.

Ryan Nagy

Saturday 12th of December 2020

One of the best posts that I have read about moving to Italy. Thanks for the no b.s. descriptions. I am an American with 10 years living and traveling in Mexico (with my girlfriend and my two dogs and cat) and I am realizing how easy we have it. Italy is on my radar as with some legal help I should be able to get ahold of my grandparent's birth certificates in Northern Italy and apply for a residency permit. Though, let's be honest - there are many ways to get derailed by the Italian bureaucracy. Our back-up place is the new Estonian digital nomad visa which seems relatively easy to get. Peace! Thanks for keeping it real.


Thursday 30th of April 2020

I've enjoyed reading your blog but I was irritated when desperate you thought about Popping back to England to use the health service to give birth. When did you last pay any tax here if at all. Just because your entitled it doesn't make it right.

Anna Karsten

Thursday 30th of April 2020

I've been paying taxes and NS in England for quite a while actually, LOL. ;-)


Friday 17th of January 2020

Two words: Northern California! Girl, I grew up in Los Angeles, I have NO idea how anyone lives down there after I found Northern California. If you want beauty like LA but beautiful hills at an affordable price, look at Lake Tahoe. I live in Rocklin, CA, it’s mellow. But just 20-min away are the mountains and about 1.5 hours is Lake Tahoe. It is beautiful. You should check out that area. Or anything between Rocklin and Lake Tahoe. You can enjoy the same ins you had. So sorry you had to deal with that mess. But you are the FIRST person I have read that has been honest about medical insurance as someone who is self employed. I always wanted to know how that worked and I wish more people shared that “business” side of thing; medical insurance, taxes, what happened when you are in another country and get sick, have a baby, stay too long, visa mess, the ins and outs of rules in different countries. Thank you!!!

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