La Dolce Vita Letter #2 — Italy vs Portugal vs Spain: Which Wins?
This Week in Italy
Five things you need to know right now:
1. 100 Italian chefs just broke a world record — with tiramisu.
One hundred Italian chefs gathered in London and set a new Guinness World Record by preparing a tiramisu stretching 440.6 metres long. The previous record of 273.5 metres had stood since 2019.
Only in Italy would a world record involve dessert.
2. Naples bank heist — straight out of a movie.
Three masked robbers held 25 people hostage during a bank heist in Naples earlier this month — then escaped through a tunnel connected to the city's sewer network. Italian authorities are investigating.
The Neapolitans, naturally, are calling it impressive.
3. Italy celebrated Liberation Day — April 25.
Italy marked the 81st anniversary of its liberation from fascism, with marches, memorials and cultural events across the country. A reminder that modern Italy is only 81 years old as a free republic — younger than many of your parents.
4. Vespa turns 80.
From its first prototype in post-war Italy to a worldwide design icon, Vespa is celebrating its 80th anniversary with events across Tuscany.
If you've ever wanted to ride one through Italian streets — this is the year.
5. Scientists warn Venice may be unsavable.
Researchers warn that rising sea levels now pose an existential threat to Venice that no adaptation measure can fully address. The city that has survived for 1,500 years may face its greatest challenge yet.
Compare expat health plans and get a free quote here:
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Town Spotlight
Every week I will do a short spotlight review of one town worth knowing.
SIRACUSA, SICILY
Founded by the Greeks in 734 BC, Siracusa is one of the oldest and most beautiful cities in the Western world. The historic island centre of Ortigia is completely walkable — narrow Baroque streets, a cathedral built on a Greek temple, fresh seafood at the market every morning. Catania Airport is 40 minutes away.
A comfortable life here costs €1,500–1,800/month. Property in Ortigia runs €2,100–2,700/sqm. Stunning, well connected, and surrounded by towns qualifying for the 7% flat tax.
Founded by the Greeks in 734 BC, Siracusa is one of the oldest and most beautiful cities in the Western world — and one of the most underrated places to retire in Italy.
The historic island centre of Ortigia is completely walkable. Narrow Baroque streets, a cathedral built directly on top of a Greek temple, a waterfront market where vendors sell fresh swordfish every morning, and the Mediterranean on three sides. No car needed. Catania Airport is just 40 minutes away.
What it actually costs to live there: Rent: €500–800/month for a 1-2 bedroom in Ortigia Utilities: ~€194/month combined Groceries: ~€300/month for one person Dinner out: from €15 at a local trattoria
A comfortable life in Siracusa costs €1,500–1,800/month. Property in Ortigia runs €2,100–2,700/sqm for renovated historic apartments.
Why it works for retirees:
Walkable, car-free historic centre
Strong expat community — British, American, German
Close to Noto, Ragusa and Modica for day trips
Excellent fresh food and outdoor markets year-round
Surrounded by towns qualifying for the 7% flat tax
Siracusa rewards slow living. If you want beauty, history and the Mediterranean at your doorstep — without paying Taormina prices — this is your town.
Your Question Answered
Every week I will answer one question from my Youtube Channel subscribers, or from my SKOOL Community members.
How does Italy calculate the tax
basis on foreign assets — purchase price,
current value, or tax records?
Question:
"How does Italy calculate the tax basis on foreign assets — purchase price, current value, or tax records?" — Ray, community member
Great question Ray — and one that trips up a lot of Americans moving to Italy.
The short answer is: it depends on the asset.
For capital gains on stocks, funds and financial investments — Italy uses the original purchase price as the cost basis. The gain is the difference between what you paid and what you sold it for. The standard capital gains tax rate is 26% flat. Taxing
For real estate — Italy calculates capital gains the same way: selling price minus original purchase cost. However if the property was your principal residence or you owned it for more than five years, the gain is completely exempt from capital gains tax. Travelsphere
For IVIE and IVAFE — these are annual wealth taxes on assets you hold, not sell. IVIE applies to real estate you own outside Italy, IVAFE to financial accounts and investments abroad. These are calculated on the current value of the asset each year — not the purchase price.
One important flag for Americans: Italy requires you to report all foreign assets annually in Section RW of your tax return. Missing this is not a minor oversight — the penalties are significant.
This is exactly why speaking with a US-Italy cross-border tax specialist before you make the move is so important. Email me at op2001il@gmail.com and I'll connect you personally.
My Latest Youtube Video
Italy vs Portugal vs Spain — Which Is the Best Retirement Option?
This is the question I get asked more than any other. So I decided to answer it properly.
In this video I compare all three countries head to head across the categories that actually matter for retirement:
Cost of living — what your money really buys in each country
Taxes — Italy's 7% flat tax vs Portugal's defunct NHR vs Spain's Beckham Law
Healthcare — quality, access and what it costs as a foreigner
Visas — how easy it actually is to get residency in each country
Lifestyle — climate, culture, language and day to day life
Spoiler: the results might surprise you. Portugal used to dominate this conversation. That's changed.
Italy vs Portugal vs Spain — Which Is the Best Retirement Option?
One Thing To Do
Check out and maybe join us in the Italy Relocation Planning Club — your first 7 days are completely free.
Tax questions, visa questions, town recommendations, real budgets from people already in the process. If you're serious about making this move, this is where the real conversations are happening.
https://www.skool.com/italy-relocation-planning-club-4251/about
