🌍 Travel: Vagabonding through Italy

As a self-employed digital nomad in 2024- What is it like?

As I write this I am in Pompei, Napoli, Italy.

So, what's it like being a digital nomad in Italy? Just as you would expect: Marvelous.

My days consist of tours, trying out delicious food, writing in this blog, working on my upcoming YouTube channel among other marketing things with my brilliant daughter, the digital marketer, and working on my Fractional CFO/Controller business Yari Solutions with my team.

I am eating one of the most popular cuisines of our time. Having amazing espressos and cappuccinos, and visiting interesting and beautiful places. I also have to get work done, stay motivated to do certain tasks, push myself to work out (a struggle because I like to be in my mind too much, not my body), meditate, and keep up mental and physical self-care.

What does it take to become a digital nomad in Italy?

First off, I have an american passport. We’re allowed anywhere from 30 to 90 days of tourism time in most countries. I recently found the least amount of time allowed for an American to be only 14 days in Oman. That’s a country I want to visit so I will have to schedule it with other Middle Eastern countries because it’s such a short time. I also found out that Vietnam for example doesn’t just let us come in with only our passport as most other countries do. An online tourist visa must be completed in order to come into the country.

In Europe, we’re allowed up to 90 days in the entire Schengen area in any 180- period. Meaning, every 6 months, you can stay up to 3 months. You must leave when the time is up or else you’re fined a hefty fine and can face possible banning of ever coming back. Not following immigration laws is considered a serious thing. You’re staying somewhere you’re considered an “illegal.”

Yes, for Americans who think that only exists in the United States, they have it wrong. This applies in ANY country.

To enter Europe on a tourist visa, or as a tourist, you don’t need to complete anything in person in your home country at a local consulate or online, as you’re required to do to enter some countries even if it’s just for tourism. Your passport is enough. It will get stamped when you come in and when you leave.

This is how I’m currently exploring Italy as a digital nomad, on a tourist visa.

If you or I wanted to have an extended stay in any country, one must apply for a visa. There are different types. At the moment, a lot of digital nomad visas have opened for remote workers, freelancers and self-employed individuals like myself.

Trading Comfort for Adventure

It was my choice to trade comfort for adventure.

It can be lonely at times doing it solo. You miss the familiar. You miss your friends and family. For me that is my kids and my dogs pretty much. You sometimes miss that feeling of "comfort" the God-awful routine affords us. I realize some people thrive on and love routine. That's not me. For that reason, I don't miss it for long. I'm not there yet in my vagabonding through Italy. It's only been 3 1/2 weeks. It's fine for me and I find things to do if it gets lonely.

I'm 5 days away from being in Italy for a month. What I started feeling in the last few days was a need to work, a need to create, a need to be productive. Of course I've been answering emails, getting through some of the long-term to-do list, managing and directing my team, and answering some client requests the entire time. I've been feeling like doing more creative right-brain work than my finance logical left-brain work, such as writing in this blog a lot to recount my experiences, post the beautiful pics in my social media, journaling, etc.

There’s always the issue of acclimating to different time zones. It took me 5 days just to feel normal in the European time zone. I was up when they were asleep and super sleepy or napping while the day eluded me. The beautiful sights you get to see and the experiences you get to have are all an epitome to the small amount of stress you must experience to live this kind of life.

It ‘s much easier when you book an AirBnb for a month, or two or three and stay in the same place. This is not the type of trip I'm having this summer.

I planned to jump around to as many Italian cities and towns in Italy as I could. This is much more stressful and requires constant planning. The constant travel to-do list and stress can keep you up. For example, the stress of the move (I don't know if I'll ever be able to describe or communicate the level of stress of that last move out of Florida), getting to Miami on the train, my first stop, while the move didn't seem to end, leaving for Italy and the inability to sleep during a 9-hour flight (I don’t know why I didn't carry my Valerian root capsules with me), the arrival in Rome and difficulty finding my host in the airport, and the one-hour drive to Viterbo —all of it! All of it combined took me 4 days to recover! It was only five days after arriving in Italy that I was able to sleep a full night. Before that I was running on 2 hours of sleep here, 3 hours there…

What to do with all this free time when you’re a solo traveler

One of my past times/side projects is day trading in the stock market. One thing I'm loving about the European time zone is that when the stock market opens at 9:30am United States Eastern Standard Time (EST) when it’s 3:30 pm here in Italy! I can spend a whole day exploring and adventuring through towns and cities in Italy and come back and day trade if I want.

Something else I like to do is read a lot. It's one of my favorite pastimes. Just like movies, books transport you to another time and place. You get to travel in your mind without moving from your bed or couch.

The third thing to do is join local tours, classes, and/or events to socialize. You will meet some really cool people along the way. Even if you don't stay in touch or see them again, meeting them will enrich your nomadic experience by simply sharing your lives.

Another cool thing about vagabonding or digital nomading is that you get to change your routine often the way I like. I started working out again when I got to Italy alone because I have so much time in my hands. I started delaying my black espresso in the morning, which is very beneficial when you're over 40 to reduce cortisol levels upon waking up, and working out helped me do that. I used my son's workout videos of working out at home that he happened to publish right before I got to Italy.

When nomading like this you have to be ready for things to not go your way or even not feeling like following through on a planned activity. So far, I had one tour canceled due to a national holiday and I purposely missed a photoshoot I had scheduled in Rome because I wasn't up for it.

It's an unpredictable path and one meant for people who don’t enjoy living in routine. Those who embrace the unexpected and who need constant exploring.

What are the visa requirements of Italy's new digital nomad visa? (or remote worker visa)

At the moment I haven’t decided if Italy is the place for me to stay for a while. If you’re interested, what do you do?

You must apply in person at an Italian consulate in your home country. Unfortunately, unlike Asia, Europe hasn’t advanced enough in technology to have this convenience for digital nomads. I find it funny that you’re trying to attract online/remote professionals and you don’t make the process available online.

It’s this type of bureaucracy that I can’t deal with. As I’ve said in other blog posts, we have had access to the use of technological tools, can we please use them correctly? Instead, governments want to use it to surveil us. There are cameras in every AirBnb, and in the city streets, but you can’t process the visas electronically like they do in Asia?

The Italian digital nomad / remote worker visa was signed into Italian law on March 28 2022. It took until April 4 2024 to become effective. They had to work out all the details of who they would allow to stay into the country for longer than the tourist visa.

They decided to aim it at “highly skilled workers.” What that means is that the Italian digital nomad visa is open to workers who have proof of income of at least three times the minimum level required for exemption from participation in healthcare costs in Italy. That figure equals out at just under €28,000 annually. Your health insurance coverage must be active during your entire stay.

The next requirement I don’t like, you must show proof that you have suitable accommodation and proof of accommodation for the length of your stay. When in a new country I’m always afraid of having chosen a good location for my accommodation. That’s not always the case and I like to be able to get out and move to another location if I have or want to. Committing to a place for 6 months gives me anxiety. Unless, you visit as a tourist first like I’m doing, spend time checking out the neighborhoods and accommodations, and choosing it that way before you go back to your home country and apply in person and sit and wait for your in-person appointment.

That’s just too many hoops to jump through and I don’t plan to go back to the states so it looks like I won’t be applying for the italian digital nomad visa any time soon. I would have to be back in the states or Puerto Rico, where they have an Italian consulate to sit there and apply in person like it’s 1985.

The next requirement is so ridiculous. You must have been a digital nomad or remote worker elsewhere for at least six months previously. Why? That actually decreases the chances of me getting the visa because I might just like it more somewhere else and never look back!

Also, you will need to go to a valid diplomatic-consular office and submit a declaration signed by your employer before any visa will be granted. In my case I’m self-employed. The LLC is mine, so what then?

Last but not least, not everyone can apply. People with recent criminal convictions, or more specifically, who have been convicted of a crime within the last five years, even with a non-definitive sentence, will be automatically rejected from the visa process.

This is all a sign to me that Italy is not for me at this time. It’s too much red tape. It shouldn’t be this hard. You should be able to prove your business or your “highly-skilled” position and apply with all your documentation online. Period.

Why make it so difficult? Because they only want the type of people who are willing to jump through these hoops. My guess is, people who like to follow silly, unnecessary rules. No thanks.

How is the internet for digital nomads in Italy?

I could tell most people in Italy are not up to date with the digital nomad revolution. Everyone assumes you’re here on vacation and I am not. Yes, I’m going to explore and visit SOME sites and places tourists visit, but I also work as I’m traveling so I have needs that the vacationers don’t. The internet hasn’t been great. I’ve lost GPS connection many times. People don’t use Google maps to navigate. I’ve had to help drivers find my accommodation using Google maps. It’s archaic.

Why am I surprised? United States fought for independence from an European country because the laws and taxes were suffocating. Why did I think I would like it here? Some things are more ahead than United States but not much.

How long do you get to stay with Italy’s digital nomad / remote worker visa?

One year. You can renew if you meet the additional requirements.

Can you bring family members under Italy’s digital nomad visa?

This is a big one for me because my 17 year old son is still “under my roof” and travels with me wherever I go. They say you’re allowed to bring family members but guess what? “Italy’s police headquarters have the final word on whether a residence permit for family reasons can be given” according to this article in EuroNews which is where I got my update on this the italian digital nomad visa.

Will I pay taxes in Italy as a digital nomad?

Yes, you will. It’s best to consult with a tax professional focused on digital nomads in Italy.

So, according to EuroNews, “Those interested need to book an in-person appointment at an Italian consulate in their country of residence. 

You are required to bring documentation including a valid passport, proof of employment, proof of income, health insurance, proof of accommodation in Italy and a criminal record certificate. 

Once your visa is approved, you have eight days from your arrival in Italy to apply for a residence permit, also known as permesso di soggiorno.” 

Final thoughts?

I get a headache just thinking about this application process.

Bottom Line: It’s too much for me. I’m turned off from it. I can’t believe I dreamed of going to Italy for 30 years. I’m finally here and now that the dream is fulfilled it’s not the place I would stay at as I once thought I would. 

It’s so ironic and hypocritical that Italy’s digital nomad visa is only to be given to those with "advanced technological means" yet you must jump through hoops as if we don’t have technology available like it’s- you guessed it!- 1985!!! LOL