Moving to Italy This Year? 5 Questions to Ask Yourself
- Su Guillory

- 1 day ago
- 4 min read
Ah, a new year and a fresh start full of possibilities. If you're like me, you've made a list of New Year's Resolutions. Is moving to Italy at the top of that list? Yay! I can't wait for you to discover the joys of living in Italy as an expat.

I'm a firm believer that no goal will be achieved without action. To that end, grab a notebook and spend some time thinking about these questions.
Why Do I Want to Move to Italy?
This is a BIG question. On the surface, your response might be "I want to live la dolce vita." Or..."I want to get away from the crazy chaos in my country."
My first piece of expat coaching advice: find a reason to move toward Italy, not to run away from the problems in your home country. Problems go away (administrations change). Or they follow you, if they're personal. You need to find the real, deep reason why Italy's calling you.
Curious about my reasons?
My son graduated from high school. I was divorced. I was ready to do something for myself that lit me up.
I wanted to get away from the hustle culture of America and embrace a slower, more deliberate way of life in Italy.
I wanted to be surrounded by beauty.
I wanted to immerse myself in another culture.
So what are your WHYs?
What Will I Do For Work?
A lot of people assume they can just decide to move to Italy and the country will welcome them with open arms. Not so. You'll need a visa, and in order to get a visa, you'll need a plan for work. That might mean looking for a job, which can be challenging, depending on where you plan to move and how good your Italian is.
If you've been working as a freelancer online, you may be able to continue to do that work with the digital nomad visa or self-employment visa.
My point here is: do your homework and see what options are available. If you need to look for a job, see what jobs are listed and the requirements. It may be tricky to find a company willing to sponsor you as an expat if there are plenty of talented Italians who would be a good fit for the role.
Where Do I Want to Live?
Ah, another big question! You may have been to Rome a dozen times and know that this is most definitely the city for you. Or you may have traveled all over and have no clue where you should land. Or...maybe you've never even been to Italy, so you're even more confused.
My first piece of advice here is to make a list of the things you want. Do you want to be in a big city or a small town? Mountains or sea? Hot or cold? A town with lots of expats or not?
Next, come visit. Book an Airbnb for a few weeks if you can, and get to know a town or city. Pretend you live there. When you visit a place on vacation, it's a very different vibe.
Make friends. Find expats (look for Facebook groups). Ask all your questions about what it's like to live there. This will help you narrow it down.
What's My Timeline?
Moving to Italy involves a lot of moving parts. On the bureaucracy side, you'll need to allow time to apply for and receive your visa. For me, this took about six months, but it will depend on the type of visa you're applying for and whether there's a specific time period when you can apply.
You also may need to find housing, at least temporarily. That may involve visiting Italy and finding a rental. Most visas will require a rental contract, so keep that in mind.
Then on the other side, you have all the logistics of getting rid of everything you own, packing up the rest, selling your house, and taking that one-way flight.
Who Can Help Me?
I'm not just saying this because I'm an expat coach who helps people move to Italy...you're going to need help. I hired a lawyer to assist with the visa process, and it was so much less of a headache.
I didn't know expat coaches existed when I moved, and honestly, I struggled. I struggled with feeling like I was in The Upside Down, where everything was contrary to how I thought it should be done. I felt alone. Exhausted.
My experience is what led me to become an expat coach. I know how big a thing it is to untether yourself from everything that you know to start over in a new country. Whether you want to work with me or someone else (even a therapist might be helpful!) I encourage you to build your support team before the move.
Once you've answered these questions, the fun begins! Spread the work out over the months leading up to your target move date so you don't get overwhelmed.
I'm here to help you on your journey however I can. In bocca al lupo!




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