The Hard Road to Italy: One family's battle for the Digital Nomad Visa
02/12/25 • 44 min
Moving to Italy is a dream for so many people—but let’s be real, getting here isn’t always smooth sailing. Italian bureaucracy is a beast of its own, and whether it’s consulates, comune offices, or the questura, every office seems to have a different answer for the same question. It’s confusing, it’s frustrating, and it’s easy to get caught up in misinformation or, honestly, just go with the answer you want to hear rather than the right one.
In today’s episode, I’m diving into what it really takes to navigate this system without losing your mind. And to help me illustrate just how unpredictable this process can be, I’m sitting down with Jenna and Damien—a couple who were among the first to apply for and actually get the Digital Nomad Visa from the Los Angeles consulate. But let me tell you, their journey was anything but easy.
Jenna and Damien started out with a completely different plan. They were thinking about moving to Florida, but a chance conversation at Disney World (yes, really!) changed everything. That led them down the path to Italy, where they found themselves knee-deep in visa applications, legal consultations, and a consulate appointment that felt more like an interrogation than an interview. Even with all the prep work they did—including hiring a lawyer—they still faced unexpected curveballs, delays, and last-minute document requests that nearly derailed everything.
Their story is a masterclass in resilience and persistence. It’s a reminder that no matter how much you plan, things will go sideways at some point—but that doesn’t mean you should give up. We’re going to unpack what went wrong, how they pivoted, and the biggest lessons they learned along the way.
And of course, I’ll be sharing my best tips to help you avoid these same pitfalls, from how to prepare for the unexpected to why flexibility might just be your best asset in this whole process.
So whether you’re deep in your visa application, just starting to explore your options, or even just daydreaming about a life in Italy, this episode is packed with real stories, practical advice, and plenty of encouragement to keep you moving forward.
Let’s get into it!
Resources:
Book a private consultation with me
About the Digital Nomad Visa for Italy
Rate, Review, & Follow
If you loved this episode and want to hear more, please consider rating and reviewing my show! This helps me support more people — just like you — to move toward their new life in Italy and live the life they deserve.
Tap to rate with five stars, and select “Write a Review.” Then be sure to let me know what you loved most about the episode!
Also, if you haven’t done so already, follow the podcast. I’m adding new episodes every week and, if you’re not following, there’s a good chance you’ll miss out. Follow now!
If you want to learn more about ways that my team and I can help you live your dream life in Italy, visit us at www.smartmoveitaly.com or send me an email!
Until next time!
Ci vediamo!
Mentioned in this episode:
Moving to Italy is a dream for so many people—but let’s be real, getting here isn’t always smooth sailing. Italian bureaucracy is a beast of its own, and whether it’s consulates, comune offices, or the questura, every office seems to have a different answer for the same question. It’s confusing, it’s frustrating, and it’s easy to get caught up in misinformation or, honestly, just go with the answer you want to hear rather than the right one.
In today’s episode, I’m diving into what it really takes to navigate this system without losing your mind. And to help me illustrate just how unpredictable this process can be, I’m sitting down with Jenna and Damien—a couple who were among the first to apply for and actually get the Digital Nomad Visa from the Los Angeles consulate. But let me tell you, their journey was anything but easy.
Jenna and Damien started out with a completely different plan. They were thinking about moving to Florida, but a chance conversation at Disney World (yes, really!) changed everything. That led them down the path to Italy, where they found themselves knee-deep in visa applications, legal consultations, and a consulate appointment that felt more like an interrogation than an interview. Even with all the prep work they did—including hiring a lawyer—they still faced unexpected curveballs, delays, and last-minute document requests that nearly derailed everything.
Their story is a masterclass in resilience and persistence. It’s a reminder that no matter how much you plan, things will go sideways at some point—but that doesn’t mean you should give up. We’re going to unpack what went wrong, how they pivoted, and the biggest lessons they learned along the way.
And of course, I’ll be sharing my best tips to help you avoid these same pitfalls, from how to prepare for the unexpected to why flexibility might just be your best asset in this whole process.
So whether you’re deep in your visa application, just starting to explore your options, or even just daydreaming about a life in Italy, this episode is packed with real stories, practical advice, and plenty of encouragement to keep you moving forward.
Let’s get into it!
Resources:
Book a private consultation with me
About the Digital Nomad Visa for Italy
Rate, Review, & Follow
If you loved this episode and want to hear more, please consider rating and reviewing my show! This helps me support more people — just like you — to move toward their new life in Italy and live the life they deserve.
Tap to rate with five stars, and select “Write a Review.” Then be sure to let me know what you loved most about the episode!
Also, if you haven’t done so already, follow the podcast. I’m adding new episodes every week and, if you’re not following, there’s a good chance you’ll miss out. Follow now!
If you want to learn more about ways that my team and I can help you live your dream life in Italy, visit us at www.smartmoveitaly.com or send me an email!
Until next time!
Ci vediamo!
Mentioned in this episode:
Previous Episode
From Toronto to Torino: How One Canadian Took the Leap to Live in Italy
In this episode of A New Life in Italy, I’m diving into the thrilling, sometimes nerve-wracking experience of packing up your life and moving to Italy. Hi, I’m Samantha Wilson, and today, I’m joined by Vanessa Reid, a Canadian content creator who took the leap and relocated to Torino just eight months ago.
Vanessa’s story is all about bravery, determination, and embracing the unknown. Imagine moving to a city you’ve never even visited before! She shares why she chose Torino—spoiler alert: affordability and a rich history had a lot to do with it—and how being a dual citizen helped her navigate the logistical challenges of relocating, though not without its own set of hurdles.
We talk about what it’s really like to choose the "right" city in Italy and dig into Vanessa’s early struggles, from language barriers to the cultural differences that make meeting new people, especially locals, a unique challenge. Torino, with its reserved yet warm residents, taught her a lot about persistence and connection.
Vanessa also gets real about the emotional rollercoaster that comes with such a huge life change—the excitement of a fresh start, the loneliness of leaving your comfort zone, and the joy of slowly building a community. She shares how she used social media to connect with both locals and fellow expats, proving that even in a brand-new country, you can find your people.
And of course, we couldn’t skip the food! Vanessa takes us on a mini culinary tour of Torino, sharing her favorite Piedmontese dishes and must-visit restaurants. Let’s just say, if you weren’t hungry before, you will be after hearing this part!
Whether you’re dreaming of moving to Italy, curious about life as an expat, or just here for some inspiration and laughs, this episode has it all. Vanessa’s journey is a reminder that big, bold moves are possible, even if they come with a few bumps along the way.
So, pour yourself a coffee or a glass of wine, and let’s chat about what it really takes to start a new life in Italy—highs, lows, and everything in between!
Resources:
A New Life in Italy Membership
Immobiliare.it (property site)
Idealista.it (property site)
Rate, Review, & Follow
If you loved this episode and want to hear more, please consider rating and reviewing my show! This helps me support more people — just like you — to move toward their new life in Italy and live the life they deserve.
Tap to rate with five stars, and select “Write a Review.” Then be sure to let me know what you loved most about the episode!
Also, if you haven’t done so already, follow the podcast. I’m adding new episodes every week and, if you’re not following, there’s a good chance you’ll miss out. Follow now!
If you want to learn more about ways that my team and I can help you live your dream life in Italy, visit us at www.smartmoveitaly.com or send me an email!
Until next time!
Ci vediamo!
Mentioned in this episode:
Next Episode
Taking the Leap—How Tanya & Davide Moved to Italy and Built a New Life
Have you ever caught yourself thinking, One day, I’ll move to Italy? You’ve got the dream, but maybe you’re waiting for the perfect moment—retirement, more savings, or just the right timing. Well, today’s episode is going to make you rethink that approach.
I had the absolute pleasure of sitting down with Tanya and Davide Raso, a couple who decided that waiting wasn’t an option. They packed up their life in Minnesota, moved to Italy ahead of their retirement plans, and started a brand-new business while navigating the ups and downs of expat life.
We get into the real conversations—what pushed them to move before they originally planned, how they chose the right town (spoiler: it wasn’t random!), and what it’s actually like to start a business in Italy. They didn’t just settle for a dream; they turned it into something tangible with their travel business, Amici Vacations, which helps people experience Italy in a deeper, more meaningful way.
But it wasn’t all smooth sailing. From adjusting to cultural differences to understanding how important connections are in Italy, they share some of the unexpected lessons they’ve learned along the way. And yes, we also talk about the bureaucratic headaches—because, let’s be honest, moving to Italy isn’t just sipping wine on a sun-drenched terrace.
This episode is for anyone who’s been sitting on the fence about moving to Italy. If you’re worried about when is the right time, how to plan your move, or whether you can make it work financially—this conversation is going to give you the inspiration (and maybe the push) you need.
So, grab your coffee, settle in, and let’s dive into what it really takes to make a life in Italy happen—no more waiting for “someday.” Tanya and Davide’s story is proof that someday can be right now.
🎧 Hit play and join us for this inspiring conversation!
Resources
Experience Italy with Friends Podcast
Rate, Review, & Follow
If you loved this episode and want to hear more, please consider rating and reviewing my show! This helps me support more people — just like you — to move toward their new life in Italy and live the life they deserve.
Tap to rate with five stars, and select “Write a Review.” Then be sure to let me know what you loved most about the episode!
Also, if you haven’t done so already, follow the podcast. I’m adding new episodes every week and, if you’re not following, there’s a good chance you’ll miss out. Follow now!
If you want to learn more about ways that my team and I can help you live your dream life in Italy, visit us at www.smartmoveitaly.com or send me an email!
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