Mediterranean Retirement Showdown 2025: Greece or Italy

I’m not going to lie to you – Expats rarely regret moving to Italy or Greece. But when they do, it’s because they picked the wrong one for their situation. 

I’ve lived in both of these countries, helped dozens of Americans relocate to each, and I’ve seen what draws people to each destination – and on the other hand, why they pack their bags and leave. 

Both offer that romantic Mediterranean retirement straight out of a dream. But here’s how to pick the right one for YOU. First, let’s break down Greece.

Retirement in Greece

So why are over 25,000 Americans calling Greece home? Let me break down what makes this country so attractive – and what might drive you absolutely crazy.

The Pros of Retiring in Greece

Let me start with the big one – taxes. When I first learned about Greece’s tax deal, I thought it was too good to be true. Greece offers a flat 7% tax rate on your foreign retirement income for 15 years. Not a typo. Your Social Security, your pension, your 401k distributions – all taxed at just 7%.

Think about this for a second. If you’re pulling $80,000 a year from retirement accounts and paying 22% in the US, that’s $17,600 in taxes. In Greece? Just $5,600. You’re saving over $12,000 every single year. Over 15 years, that’s $180,000 staying in your pocket instead of going to Uncle Sam.

But money isn’t everything. The cost of living in Greece will shock you – in a good way. I’ve had clients tell me they’re living better on $3,000 a month in Greece than they were on $6,000 in Arizona.

Here’s what I mean: A nice two-bedroom apartment in Thessaloniki runs about $600 a month. Fresh fish at the market? Maybe $8 per pound. A three-course dinner at a local taverna with wine? $15. Getting your teeth cleaned? $30. When our client Sarah moved from Denver to Crete, she said her grocery bill dropped from $150 per week to $60 – and she was eating better food.

The lifestyle is what really gets people hooked. Greece is one of those Blue Zone places where people live longer and healthier lives. The Mediterranean diet isn’t just trendy here – it’s how everyone actually eats. Fresh olive oil, fish, vegetables, minimal processed food. Plus, the pace is slower. People take time for long lunches, afternoon naps, evening walks.

Safety is another huge plus. Greece ranks as one of the safest countries in Europe. I’ve walked around Athens at midnight and felt completely comfortable. Violent crime is rare. You’re more likely to get invited to someone’s house for dinner than robbed.

And here’s a perk most people don’t think about – with Greek residency, you get access to all 27 Schengen countries visa-free. Want to spend a month in Italy? No problem. Week in Germany? Go for it. You’re basically getting a European passport without the 10-year wait.

How to Move to Greece

You’ve got two main paths here, and they’re pretty straightforward.

Option one is the FIP visa – that stands for Financially Independent Person. You need about €3,500 per month in passive income. That’s around $3,800. This has to come from pensions, Social Security, investment dividends, rental income – not a job. The upside? No investment required. The downside? You must spend at least 183 days per year in Greece to keep the visa. For most retirees, that’s not a problem.

Option two is the Golden Visa. Invest €250,000 in a property that needs renovation, or €400,000 in regular residential property in low-density areas. If you want to live in Athens or on popular islands like Mykonos, you’re looking at €800,000. But here’s the kicker – with the Golden Visa, you get immediate permanent residency with zero stay requirements. You could spend 10 days a year in Greece and keep your residency. Perfect if you want flexibility.

One of our clients, Jim from Texas, went the Golden Visa route. Bought a €400,000 house on Crete with a sea view. He spends winters there and summers back in Texas. His property has appreciated 15% in two years, so he’s basically getting paid to have European residency.

The Cons of Retiring in Greece

Now for the stuff that drives people crazy. Greek bureaucracy is legendary – and not in a good way. Simple tasks that should take an hour can take all day. Getting your tax number? Plan for three trips to different offices. Opening a bank account? Bring a translator and your patience.

One client told me it took six months to get internet installed at her house. Six months. She was using her phone’s hotspot to work from home for half a year because the bureaucracy moved so slowly.

English proficiency drops fast outside tourist zones. In Athens and the islands, you’ll get by fine. But move to a smaller town, and you’re going to need some Greek. The language is tough – it’s got a completely different alphabet and grammar structure that’s nothing like English. Even basic phrases take time to learn.

The infrastructure can be frustrating, especially on the islands. Power outages happen. Water pressure is weak. Internet can be spotty. Don’t expect everything to work like it does back home. Our client Maria from California said the hardest adjustment was accepting that “island time” meant things happen when they happen, not when you want them to.

Healthcare is a mixed bag. Private healthcare is excellent and cheap – you’ll pay $50 to see a specialist, $100 for an MRI. But the public system is overwhelmed and slow. Most expats get private insurance, which runs about $100-200 per month and gives you access to good doctors and hospitals.

And let’s talk about summer heat. July and August can hit 100°F regularly, especially on the islands. There’s no escaping it. Air conditioning bills spike. Everyone moves slower. If you hate heat, you’ll hate Greek summers.

Weather can be unpredictable too. I’ve seen it rain for two weeks straight in November, flooding streets and making everything damp and gray. The sunny paradise image isn’t wrong, but it’s not 365 days a year either.

Now let’s flip over to Italy and see how it compares…

Retirement in Italy

Now let’s talk about Italy, a country that over 15,000 Americans have chosen as their retirement home. And honestly, I get it. I’ve spent a few months in the country the last few years and really enjoyed my time there, even in the fabled Southern Italy. 

But Italy offers something Greece doesn’t: A realistic path to citizenship.

The Pros of Retiring in Italy

Let me start with the lifestyle because that’s what hooks most people. Imagine walking to the local market every morning, chatting with vendors who know your name, buying tomatoes that taste like what tomatoes should taste like. Our clients consistently tell us the quality of life in Italy feels more intentional, more connected than even they had expected.

The food culture alone changes how you live. Italians don’t grab fast food for lunch. They sit down for two hours, enjoy organic meals, talk with friends. Dinner starts at 8 PM and goes late. Everything slows down between 1-4 PM for riposo. The pace forces you to enjoy life instead of rushing through it. I personally love this model for our expat retirees.

But let’s talk tangible numbers. Italy has a 7% flat tax regime, but with a catch – you have to live in a Southern Italy town with fewer than 20,000 people. Think Calabria or Sicily, not Rome or Milan. The tax rate applies to retirement income for 10 years, which is 5 years shorter than Greece’s special tax regime, but it’s still massive savings and together with the US-Italy double tax treaty, could reduce your taxes to miniscule amounts. 

Here’s what really surprised me about Southern Italy – you can buy decent homes for under $50,000 and fixer-uppers for far less. Not kidding. Our client Robert bought a 3-bedroom, 200-square meter house in Abruzzo for €35,000. It needed work, but even after renovations, his total investment was under $100,000. Try finding that anywhere in the US.

Healthcare in Italy is good and cheap. Private insurance runs about $150 per month and gives you access to top-tier doctors. An MRI costs $200. Heart surgery? Maybe $50,000 instead of $150,000. Plus, the preventive care mindset means doctors actually spend time with you but don’t expect this universally throughout the country.

The big advantage Italy has over Greece in my opinion? Citizenship. After 10 years of legal residency (meaning 270 or more days a year), you can become an Italian citizen. That’s an EU passport that opens doors everywhere. And if you have Italian parents, you might qualify for citizenship by descent without ever even setting foot in the country. And just a heads up – If you read somewhere that this law permits descent from even farther back, that’s outdated information after Parliament passed a new law earlier this year.

How to Move to Italy

So if this all sounds great to you, how do you move? Well, Italy gives you two main paths, and both are pretty achievable. We’ve broken this down in another video and will link that at the end of today’s.

The Elective Residence visa is perfect for retirees. You need €32,000 per year per applicant (although this varies from consulate to consulate) in passive income – that’s about $35,000. For couples, it’s roughly €62,000. This has to come from pensions, Social Security, investments – not active employment. But you can’t work on this visa, which is perfect for retirees.

The process is straightforward but requires planning. You need to secure housing before you apply, show health insurance, prove your income is stable, etc – all requirements that the Freedom Files team can help you with. But once approved, you get a renewable residence permit that leads to permanent residency after 5 years.

Option two is the Italian Investor Visa. You must invest €250,000 in an Italian startup or €500,000 in an existing business. This gives you a 2-year visa that renews for another 3 years. After 5 years, you can apply for permanent residency. The upside? One, you’re not restricted to just passive income. Two, you do not need to relocate to Italy nor spend any time there to maintain your visa, which means no required tax residency. Three, you can continue working if you so please. And finally four, you don’t even have to make the investment until after you’re approved for the residency, which reduces major risk. No other European golden visa program offers this feature.

One of our clients, Lisa from Oregon, took the investor route. She put €250,000 into an innovative wine startup in Tuscany. Not only does she get residency, but she’s earning about 8% returns annually and gets cases of amazing wine delivered to her door. She jokes that the wine alone makes the investment worth it.

The Cons of Retiring in Italy

Okay, so now you know the pros and legal paths of moving to Italy. But what about the downsides? We’re jurisdiction-agnostic over here, so we always report the cons as well. No place is perfect, and Italy is not an exception.

Italian bureaucracy makes Greek bureaucracy look efficient. I’m not exaggerating. Simple tasks can take months. Getting your codice fiscale (tax ID) should take an hour but might take three trips to different offices. Opening a bank account can require a translator. But surprisingly, Italian immigration offices move very quickly. You can get approved for either visa we just covered in 4-12 weeks.

The 7% flat tax has major restrictions. You must live in Southern Italy in small towns. If you want to live in Rome, Florence, or Milan and spend more than 6 months there (which is required on the Elective Residence Visa), you pay regular Italian tax rates – which can hit 45% or higher. This geographical restriction can be a deal-breaker for many people who dream of Tuscan vineyards or Lake Como.

Another downside – Language is a bigger barrier than most people expect. Italians are not as patient with foreigners as Greeks are, at least in my experience, so you’ll struggle in daily life without a little basic Italian. 

Cost of living varies dramatically by region. Northern Italy can rival Switzerland for expenses. A one-bedroom apartment in Milan runs $1,800 per month. Compare that to $400 per month in Calabria.

And if you relocate to Southern Italy for the tax and cost savings, understand that infrastructure can be frustrating as well. Power outages are common. Internet speeds are slow. Public transportation is unreliable. One client said moving from Boston to Basilicata felt like stepping back 20 years in terms of basic services, but he wasn’t swayed.

Now, here’s my personal take on which country might be right for you…

My Experience and Opinion of Greece and Italy

Before I share my honest opinion after living in both countries and helping hundreds of Americans make this choice as well, drop a comment down below and let me know what you thought of each option. Which grabs your attention more? 

Choose Greece if you want maximum tax savings and flexibility. That 15-year, 7% flat tax rate is unbeatable, and you can live anywhere in the country. Athens, the islands, wherever. The Golden Visa gives you permanent residency with zero stay requirements, perfect if you want to split time between the US and Europe – or slow traveling the world for that matter. Greece is also slightly cheaper overall and has that laid-back, organic island lifestyle that many of our retiree clients crave.

On the other hand, choose Italy if citizenship matters to you and you don’t mind geographic restrictions. That EU passport after 10 years opens doors worldwide. You’ll have the ability to live, work, study, and get treatment in not only Italy but all 27 member states of the European Union. The culture feels a bit more sophisticated, the food is arguably better, and you’re closer to the rest of Western Europe and your home in the US. 

But here’s the catch – Italy forces you into small Southern towns for the tax benefits. If you’re dreaming of Tuscan vineyards or Lake Como, you’ll pay regular Italian taxes, which can hit 45%. Greece lets you live wherever and keep that 7% rate on your retirement income. So if you’re an American citizen, you’ll be stuck paying just your US taxes with a small foreign tax credit.

For pure financial optimization, Greece wins. For long-term EU integration and potential citizenship, Italy takes it. Both beat retiring in Florida on taxes, cost of living, and lifestyle – and probably whatever else you’re thinking about.

Give us a holler if you’re considering a move abroad, and we’ll get you started down the path. It’s simpler and less stressful than you think – we promise.

If Italy’s citizenship path caught your attention, check out our complete breakdown of Italy’s immigration options on your screen. We cover the Elective Residence Visa and the Investor Visa in detail.