Italy vs. Portugal vs. Spain vs. France: Who Wins the Retirement Hunger Games?
- Caesar Sedek
- Aug 20
- 4 min read
Picture this: four couples, all sitting in the same overcrowded U.S. airport lounge, waiting for their delayed flight while CNN blares more bad news. Each one has the same thought: “I’ve had enough. Let’s get out.”
Couple One sees themselves in Liguria, sipping espresso in a seaside piazza while debating if the neighbor’s Vespa is cooler than theirs. Couple Two is already on a Lisbon rooftop, toasting cheap vinho verde and pretending they actually like sardines. Couple Three? They’re in Seville, where tapas is religion and siesta is a legal right. Couple Four has gone full French — baguette under the arm, muttering about terroir, ready to age gracefully in Bordeaux.
The fantasy is easy. The reality is trickier. Because choosing a retirement destination in Europe isn’t just about aesthetics. It’s about cost, taxes, healthcare, and whether you’ll lose your mind at the visa office.
So let’s cut through the olive oil haze and pit the Big Four against each other.
Cost of Living
Portugal: Still the bargain basement of Western Europe. Groceries, wine, eating out — all cheaper. Lisbon and Porto have climbed in price, but outside the cities you can live surprisingly well on surprisingly little.
Spain: A touch more than Portugal, but still a deal. Big city rents (Barcelona, Madrid) can sting, but coastal towns are manageable. Bonus points for cheap tapas — your dinner bill shrinks with every plate of free olives.
Italy: Split personality. Florence, Rome, and Milan will bleed your wallet. But small towns in the south? You can practically rent a villa for what you’d pay for a parking space in LA.
France: Paris is an insult to your bank account. But rural France — Burgundy, Dordogne, Provence — offers solid value, especially if you like good wine cheaper than soda.
Winner: Portugal, unless you’re addicted to Paris.
Healthcare
Italy: Universal healthcare that actually works. Some waits, some bureaucracy, but doctors who know their stuff.
Portugal: Public system is decent, private is cheap, and everyone raves about the dental prices.
Spain: Solid across the board. Spain consistently ranks high for healthcare quality and outcomes.
France: Rolls-Royce healthcare. Once you’re in, you’ll never want to leave. Costs are low, quality is absurdly high.
Winner: France, though Spain is snapping at its heels.
Taxes and Bureaucracy
Italy: Generous 7% flat tax in small towns, if you qualify. Otherwise, complicated but manageable if you hire a good commercialista.
Portugal: The famous NHR tax regime is sunsetting, but other breaks remain. Bureaucracy is legendary, and not in a good way.
Spain: Taxes are higher and more punishing if you’re wealthy. Bureaucracy involves enough stamps, signatures, and photocopies to fuel an entire paper industry.
France: Taxes will make you nostalgic for the IRS. But once you’ve paid, the state actually gives you something back — healthcare, pensions, infrastructure.
Winner: Italy, if you play the incentives right. Portugal second, though it’s shifting.
Housing
Portugal: Hot market thanks to foreign buyers. Still deals inland, but coastal towns are expensive now.
Spain: Plentiful housing stock, still affordable in many regions. Buying is straightforward, though paperwork is its own circle of hell.
Italy: Rural bargains galore. You can find habitable homes under €100k. Renovations are their own sport, best played with a strong liver.
France: Charming but not cheap. French property taxes are reasonable, though. And you actually get insulation.
Winner: Spain for balance, Italy for bargains, Portugal if you’re quick.
Lifestyle Vibe
Italy: Art, food, chaos, beauty. Every day is a painting, until you need a plumber.
Portugal: Laid back, gentle, friendly. The California of Europe, without the price tag.
Spain: Party, passion, plazas. If you’re allergic to noise, keep moving.
France: Cultured, chic, a little smug. But damn if they don’t make it look good.
Winner: Depends on your poison.
The Bottom Line
If you want cheap and cheerful, Portugal is still the sweetheart deal.
If you want balance — healthcare, culture, cost — Spain is underrated.
If you want romance and lifestyle, Italy’s the slow burn.
If you want sophistication and healthcare perfection, France takes the crown.
This is exactly why I wrote Greener Pastures: A Practical Guide to Retiring in Europe. Because picking a country isn’t about falling for the first postcard view. It’s about sanity, strategy, and knowing what you’re signing up for when the honeymoon wears off.
So if you’re still on the fence — or if you want the nitty-gritty on visas, taxes, and how to avoid rookie mistakes — grab the book. And keep an eye here. Next up, I’ll dig deeper into each country: the quirks, the red flags, the “no one tells you this until you’re knee-deep in paperwork” moments.
Europe isn’t perfect. But it might just be perfect for you.
Not sure if Portugal’s laid-back vibe, Spain’s fiesta energy, France’s healthcare, or Italy’s chaos-and-charm mix is right for you? That’s exactly what I help people untangle every day.
Book a free discovery call and we’ll map out which country fits your budget, lifestyle, and sanity level. No fluff, no sales pitch — just a clear plan for where to start.
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