Thinking about moving to Italy but not planning to retire?

Then at some point, probably soon, you'll face the question: what am I actually going to do for work?

In this episode of A New Life in Italy, Samantha Wilson sits down with Aisling, an Irish expat who moved to Italy, changed careers in her late 30s, and built a successful freelance business teaching English to corporate clients.

If you’ve ever considered teaching English in Italy, freelancing, or starting over in a new country, this episode gives you a real, honest look at what it actually takes.

Because the truth is… it’s not just about speaking English.

It’s about qualifications, bureaucracy, relationships, and building something sustainable over time.

Aisling shares her 10-year journey from working in the arts in Ireland to teaching business English in Milan, and eventually creating a flexible, location-independent career from her home in Tuscany.

You’ll learn how she got started, what surprised her most about working in Italy, and why relationships matter more than resumes in the Italian business world.

This episode is essential listening if you are planning your move to Italy and want to understand how to realistically support yourself once you arrive.

How to teach English in Italy and what qualifications you actually need

The difference between working for a language school and freelancing

How to set up a freelance business in Italy, including Partita IVA

Why you need a commercialista and how taxes work for freelancers

How to find clients in Italy and why networking is everything

The reality of Italian bureaucracy when starting a business

How long it takes to build a stable income as an expat

Why business English is one of the biggest opportunities in Italy

How COVID changed remote work opportunities across the country

What it really takes to build a sustainable career in Italy

Anyone planning to move to Italy and needing to work

Expats considering teaching English in Italy

Freelancers and remote workers looking to relocate to Italy

People changing careers later in life and starting over abroad

Listeners who want a realistic view of working and living in Italy

Aisling’s book: Freelance English Teaching in Italy: How to Find High-Paying Clients and Build a Sustainable Career

If you’re serious about moving to Italy and want expert guidance on visas, relocation, or building your life here, you’ll find everything you need at Smart Move Italy.

And if this episode helped you, make sure to follow the podcast and share it with someone who’s dreaming about their own life in Italy.

Because this move is possible… when you know how to do it right.

Mentioned in this episode:

Sentire Media Website

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Sentire Media Website

You’ve planned it, dreamed about it, and finally made the move to Italy.

But what happens next?

In this episode of A New Life in Italy, Samantha Wilson shares the real experience of the first 30, 60, and 90 days after arriving in Italy. This is the phase no one fully prepares you for and where most people feel overwhelmed, stuck, or unsure if they made the right decision.

If you are planning your move to Italy, currently applying for a visa, or have recently arrived and feel like things are harder than expected, this episode will help you understand exactly what is happening and how to move through it with clarity and confidence.

This is not about the dream. This is about building your life in Italy.

In this episode, you’ll learn:

What the first 90 days in Italy actually feel like beyond the excitement

Why emotional ups and downs are completely normal after moving abroad

How Italian bureaucracy really works and why nothing seems to happen in a straight line

The biggest mistakes foreigners make after arriving in Italy

How to approach your first 30, 60, and 90 days with a clear and simple plan

Why loneliness can show up even when you’re living your dream

How to stop feeling behind and start building your life with confidence

Topics covered include:

Moving to Italy for foreigners

Living in Italy after relocation

Permesso di soggiorno process explained

Italian bureaucracy and settling in

Expat life in Italy

Emotional challenges of moving abroad

Renting vs buying property in Italy

Cost of living in Italy for newcomers

Public transport vs owning a car in Italy

Listener Questions Answered:

Should you buy property in Italy before moving or rent first?

How much money do you need for your first year living in Italy?

Do you need a car to live in Italy or can you rely on public transport?

If you’re in that in-between phase where the dream has become real life and things feel harder than expected, this episode will help you reset, refocus, and move forward.

Ready to move to Italy with clarity and support?

Download our free visa guide or explore how we can help you with visas, relocation, and property at Smart Move Italy.

If this episode helped you, share it with someone who is planning their move to Italy.

And don’t forget to follow the show so you never miss an episode.

Mentioned in this episode:

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Sentire Media Website

Sentire Media Website

Have you ever noticed something strange when you visit Italy?

You eat pasta.

You eat bread.

You eat pizza.

And somehow… you feel better.

People say this to me all the time. The bread doesn’t bother their stomach. The pasta doesn’t leave them bloated. They feel healthier even though they feel like they’re eating more.

So what’s going on?

In this episode of A New Life in Italy, Samantha talks with Dr. Anna Toker, a board certified colorectal surgeon with nearly 30 years of experience studying digestive health. Dr. Toker recently traveled to Italy to explore why people here eat foods many people fear, yet still maintain better gut health and longevity. Dr. Anna Toker-transcript

Together they explore the real reasons behind the “Italy effect” including slower meals, better ingredients, smaller portions, more walking, and less stress around food.

You’ll learn why the Mediterranean lifestyle may be just as important as the Mediterranean diet and why slowing down might be the most powerful ingredient of all.

Listener Q&A

At the end of the episode Samantha answers three listener questions:

• What surprised you most the first time you visited Italy?

• Should you rent or buy when you first move to Italy?

• What is one mistake people make when planning their move?

If you’ve ever wondered why food feels different in Italy, this episode explains why.

Resources Mentioned

Dr. Anna Toker: Find her insights and educational content on Instagram and online.

Connect with Smart Move Italy

If you’re dreaming about your own new life in Italy, Smart Move Italy can help guide you through the process.

From visas and relocation planning to buying property in Italy, the team works with people from around the world who are ready to start their next chapter here.

Subscribe to A New Life in Italy

If you enjoy the show, be sure to follow and subscribe so you never miss an episode.

And if you know someone who dreams about living in Italy, share this episode with them.

Because sometimes the journey to a new life begins with one small idea… and a great conversation.

Mentioned in this episode:

Sentire Media Website

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Sentire Media Website

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What if you are not actually short on time… you are just investing it in the wrong places?

In this episode, I sit down with international time management specialist, best-selling author, and life designer Kate Christie for a conversation that is about so much more than productivity.

We talk about ownership. About intention. About what happens when life cracks you open and forces you to reassess everything. And about why “later” is a dangerous word.

Kate shares how she walked away from corporate law, rebuilt her life after profound personal loss, and now helps high-performing women reclaim more than 30 hours of guilt-free time every month. Yes. Thirty.

We dive into:

• Why you cannot “manage” time, only invest it

• The difference between a Bucket List and a Life List

• How grief reshaped Kate’s priorities forever

• The three types of goals every woman needs: Go Big, Go Small, and Go Now

• A 90-second framework you can use today to kickstart any dream

• And how buying and renovating a palazzo in Sicily became the ultimate case study in reinvention

Kate’s story is bold, honest, and deeply empowering. Her message is clear. It might be your turn.

If you have been putting something off, this episode will lovingly challenge you.

About Kate Christie

Kate Christie is an international time management expert, best-selling author, speaker, and founder of Time Stylers. She works with high-performing individuals and teams to help them reclaim their time and redesign their lives.

Her most recent book, The Life List, encourages women to stop waiting for someday and start intentionally living now.

She is currently renovating a palazzo in Alcamo, Sicily while building an “eternal summer” life between Australia and Italy.

Connect with Kate

Instagram

https://www.instagram.com/katechristieloves/

Facebook

https://www.facebook.com/kate.christie.92/

Website

https://www.katechristie.com.au/

The Life List

https://www.katechristie.com.au/books/the-life-list-new/

Palazzo Blueprint

This free resource covers the first five steps of Kate’s powerful goal framework that we discussed in this episode. If you are ready to move from dreaming to doing, start here:

https://palazzo.katechristie.com.au/

If this episode spoke to you, take 90 seconds today and write down one intention and one go-big goal.

And if that goal happens to be Italy… you know I am here to help.

www.smartmoveitaly.com

Subscribe, leave a review, and share this episode with a woman who needs to hear that it might just be her turn.

Mentioned in this episode:

Sentire Media Website

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Sentire Media Website

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No one really talks about this until it happens to you. You wake up sick in Italy and suddenly everything feels heavier. New system. New language. New rules. And a lot of what you think you know about healthcare no longer applies.

In this episode, Samantha records in real time, still in pajamas and actively sick, to walk you through what actually happens when you get sick in Italy. Not the official version. Not the perfect government website version. The real life, boots on the ground experience.

This is a must listen if you already live in Italy, are planning a move, or spend extended time here and quietly wonder what you would do if you got sick. Where do you go first. Who do you call. Do you need insurance. Can the pharmacy really help. And how do you explain what is wrong when your brain is foggy and Italian is not your first language.

You will learn how the Italian healthcare system works in practice, why the pharmacy is often your first stop, when to see a doctor, when to avoid the emergency room, and how to stay calm when everything feels unfamiliar. Samantha also shares what it is like dealing with COVID in Italy right now and why the approach here feels very different than what many people remember from past years.

The goal of this episode is simple. To help you feel calmer, more prepared, and less afraid of the what ifs. Getting sick abroad does not mean you are alone. It just means the system works differently.

What You Will Learn in This Episode

How healthcare in Italy actually works at a high level

Why the pharmacy is your first line of care and how pharmacists help diagnose and treat symptoms

Which common medications in Italy match what you may know from home

When to see a doctor and the difference between public and private care

How much private doctor visits typically cost and how fast you can be seen

How emergency rooms work in Italy and when to go to the pronto soccorso

What COVID looks like in Italy right now and how cases are managed

How to handle language barriers when you are sick and stressed

Why rest is taken very seriously in Italy and how that mindset affects recovery

Who This Episode Is For

People already living in Italy

Anyone planning a move to Italy

Long term visitors or digital nomads

Anyone nervous about healthcare abroad

Anyone who wants to feel prepared before something goes wrong

Listener Questions Mentioned in This Episode

Is it better to rent first or buy right away when moving to Italy

How do you know if a small town is livable year round and not just great for vacations

What is the one thing people should have figured out before moving to Italy to make the transition smoother

If this episode helped you, save it for later, share it with someone planning a move, or send it to a friend who worries about healthcare abroad. And if you are listening while sick, this is your reminder to slow down, rest, and trust that you are not missing anything.

New episodes every week.

www.smartmoveitaly.com

Mentioned in this episode:

Sentire Media Website

APP Link

Sentire Media Website

Planning a move to Italy with your spouse or children can feel overwhelming, especially when it comes to visas. One of the biggest mistakes families make is assuming Italy offers an automatic family visa or that loved ones can simply arrive together without careful planning.

In this episode of A New Life in Italy, Samantha Wilson walks you through how family visas in Italy actually work, why so many families get delayed or separated, and what you need to know before you make a single move.

Italy’s family visa system is not intuitive. Timing, eligibility, and sequence matter more than most people realize. Misunderstanding just one step can trigger long delays, denials, or years-long waiting periods.

If your move to Italy includes a spouse, children, or dependents, this episode is essential listening.

What You Will Learn in This Episode

• How family visas in Italy really work and why they are not standalone visas

• The difference between family reunification visas and family visas for spouses of Italian or EU citizens

• Who qualifies as a dependent under Italian immigration law and who does not

• Why adult children and parents are rarely approved without proven medical dependency

• The exact order required for family reunification applications

• What a Nulla Osta is and when it is required

• Why the Suitability Certificate is critical and often overlooked

• How entering Italy too early can trigger a two year family reunification delay

• Why showing up without a visa no longer works in Italy

• When a family visa may not be the best option for your situation

Who This Episode Is For

• Families planning to move to Italy together

• Couples where only one spouse qualifies for a visa

• Parents relocating to Italy with minor children

• Spouses of Digital Nomad, Investor, Work, or Student visa holders

• Spouses of Italian or European Union citizens

• Anyone confused about family visas, dependency rules, or timing

Key Topics Covered

• Family visa Italy explained

• Family reunification visa Italy

• Spouse visa Italy

• Moving to Italy with children

• Italian visas for families

• Nulla Osta for family reunification

• Suitability Certificate Italy

• Permesso di soggiorno for family members

• EU spouse visa Italy

• Italian immigration rules for dependents

Listener Questions Answered

• Is it too early to start planning visa timing if we are moving to Italy in a year

• Does Italy care if only one spouse qualifies for a visa

• Is it normal to feel overwhelmed trying to coordinate visas, school, healthcare, and residency

Important Takeaway

Family visas in Italy are never automatic. But they are absolutely manageable when you understand the rules, respect the required sequence, and plan ahead.

Most family visa problems are not caused by bad luck. They are caused by assumptions.

This episode gives you clarity so you can protect your ability to arrive in Italy together and start your new life without unnecessary stress or separation.

Listen to the full episode to avoid the most common and preventable family visa mistakes.

Have a Question for a Future Episode

Send Samantha Your Question

If you have a question about visas, moving to Italy, or starting a new life abroad, you can leave a voicemail using the link in the show notes. Your question may be featured in a future episode.

Ciao for now, and see you next week on A New Life in Italy.

Visit Smart Move Italy

Get the Smart Move Blueprint

Mentioned in this episode:

Sentire Media Website

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Sentire Media Website

How much does it really cost to move to Italy?

In this episode, we break down the real cost of moving to Italy so you can understand what to expect financially and emotionally before making a big decision. Not the Instagram version. Not extreme worst case scenarios you find online. Real numbers, real planning, and the real life behind the move.

In the first episode of Season 4 of A New Life in Italy, Samantha Wilson walks you through the true costs of relocating to Italy, including one time moving expenses, ongoing monthly living costs, visa and immigration fees, housing setup, and the hidden cost offsets many people overlook. We also talk honestly about the financial and emotional cost of staying where you are.

This episode is not about convincing you to move to Italy or pushing you toward a timeline. It’s about replacing fear and overwhelm with clarity, so you can decide if moving to Italy makes sense for your life, your finances, and your future.

If you’ve been dreaming about Italy but feeling stuck in the planning phase, this episode will help you see the full picture and take your next step with confidence.

Links and Resources

Download the companion workbook for this episode to walk through the numbers calmly and clearly at your own pace.

You’re not making decisions today. You’re gathering information so you can move forward with confidence when the time is right.

Visit Smart Move Italy

Mentioned in this episode:

Sentire Media Website

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Sentire Media Website

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This season finale is a look back at the questions that mattered most. The ones you saved, shared, and replayed because they helped you make smarter decisions about moving to Italy.

In this episode, I revisit our most popular topics from the true cost of living in Italy and whether €2,000 a month is realistic, to buying property, renovation surprises, investor visa rules, document apostilles, and what foreigners really need to know before making a move.

It is also a thank you. Your messages, voice notes, and stories shape this show, and being part of your journey to Italy is something I am truly grateful for.

I also share a sneak peek of season four, launching January 14, 2026, where we go deeper into real life in Italy with more behind the scenes conversations, honest debates, and updates from people actively navigating their move.

Save the parts that speak to you, share this episode with someone who dreams of Italy, and stay connected with me on Instagram or through our newsletter.

Italy is waiting for you.

Mentioned in this episode:

Sentire Media Website

APP Link

APP Link

Sentire Media Website