I've analyzed every affordable, strategically located coastal town in Italy for a €200-300K budget.

Taxes, airports, cost of living, remote work infrastructure. I've called a couple of friends to confirm the data.

10 towns. The definitive guide for FIRE and Digital Nomads in Italy.

Thread 🧵
First, why Italy in 2026?

Three reasons:

• 7% flat tax for 10 years on ALL foreign income for retirees in small towns (pensions, dividends, capital gains), 50% tax exemption for remote workers

• Property at half the price of Portugal and Croatia

• Ryanair is opening bases and routes across the South at record pace

Italy is becoming THE game.

This is Puglia, Italy.

7% flat tax for retirees (small towns only). 50% income exemption for workers. Flat-tax for HNW.

Magical region. Mediterranean coast. Authentic culture.

But most foreigners choose the wrong town and overpay by 30-40%.

I've lived across 5 continents and visited every corner of Puglia.

Here are the 7 best places - and the traps to avoid 🧵
First, LECCE - "The Florence of the South"

The obvious choice (that's actually right).

Lecce is where serious expats land when they've done their homework.

It's a proper city (95k people) with everything functional - hospitals,
universities, year-round economy not dependent on tourists.

The baroque center is legitimately stunning, not Disney-fied.

Here's what nobody tells you about Lecce...

This is Lugano:

- 0% capital gains tax
- 1 hour from Milan
- Swiss lifestyle with palm trees

This combination shouldn't exist. But it does.

Here’s why Switzerland's best-kept secret should be on your radar: Lugano is a paradox. And most miss it completely.

It sits in Ticino, Switzerland's Italian-speaking canton.

Officially it’s Switzerland – but it doesn't feel like Switzerland. Mediterranean climate, palm trees by the lake, Italian spoken everywhere. Swiss quality underneath, but none of the coldness.

And here's what's interesting…

Retiring in Italy with the 7% flat tax.

Here’s the full map: I had to build it manually because it simply didn’t exist anywhere online.

Green regions: automatically eligible. Any village under 20k residents qualifies (Abruzzo included). Plenty of great options.

Yellow regions (Lazio, Umbria, Marche): only specific villages in the official earthquake-area lists qualify. Very niche, almost unknown, harder to navigate, but absolutely possible.

For context: my grandfather’s village in Lazio hosted a Canadian family 50 years ago. They came every summer, built a villa, loved it, and everyone knew them. It was the only modern house in the whole valley. Nobody understood why they chose that place, but when you’re 15 minutes from a real town, have your own home, and want a quiet, culturally rich, food-driven lifestyle… it makes perfect sense. In retrospect, they were basically early adopters.

With that in mind, here’s a shortlist of the 5 most beautiful, American-friendly, high-amenity 7% towns in the yellow regions, close to real cities, fully on the eligible lists, and offering a charming, scenic, safe, year-round lifestyle.

*Important: this list ISN'T for everyone. In most cases, the lifestyle means owning a house there and spending plenty of time in the nearby larger city. Many of these villages are so small and niche that even most Italians haven’t heard of them.

The green regions include well-known, warmer, tourist destinations like Taormina. 1. Sarnano (Marche)
•Spa town + ski slopes nearby
•45 min to Macerata
•Excellent digital infrastructure
•Extremely charming and well kept

I'm Italian.

Everyone asks me about moving to Italy. But Italy isn't for everyone.

I've isolated 4 specific profiles. For these, it might be the best decision you ever make.

Here's who should actually consider it (and who shouldn't): First, let me be clear.

I left Italy a decade ago when it was considered a sinking ship. Brain drain, bureaucracy, stagnation.

But over the years, something has quietly shifted.

Italy is back. And it has built one of Europe's top arbitrage + lifestyle opportunities.

But not everyone…

Italy is back.

For years, I dismissed my own country as a sinking ship.

But I’ve discovered recently that Southern Italy is one of the best arbitrage opportunities in Europe.

And arguably in the world.

Here's everything you need to know to take advantage of this opportunity: First, let me be open.

As an Italian, you have no idea how happy it makes me to write...

Italy is back.

Rome is finally cleaning up. Milan is the new London. Over 100,000+ repatriates moved back with tax incentives (mainly Milan). 4,000+ applied for the €200K/year flat tax in the first half of 2024 alone.

But the real story is what's happening in the South that nobody's paying attention to…

This is Italy:

- 7% tax for foreign pensioners
- €200k flat tax on unlimited global income
- 60 UNESCO World Heritage Sites (most in world)

Now secretly one of Europe's strategic havens…ITALY IS BACK!

Here are 8 reasons why Italy should be on your radar: First, Italy’s history is totally unique:

- Ancient Roman Empire foundations
- Renaissance cultural revolution
- Post-WWII economic miracle
- 2024 strategic tax overhaul targeting global talent

As Mr History shares, even the origins of Italy are absolutely fascinating:

This is Bulgaria:

- 10% flat tax (tied for lowest in EU)
- Adopting Euro (January 2026)
- Full EU citizenship in 5 years

One of Europe's best-kept secrets just joined Schengen in 2025.

Here are 8 reasons why Bulgaria should be on your radar: First, Bulgaria's fascinating history:

- Medieval Bulgarian Empire (one of Europe's most powerful)
- 500 years under Ottoman rule
- Communist state until 1989
- EU member since 2007

From Soviet satellite to Europe's (secretly) most business-friendly tax regime in just 35 years.

Mr History does a great breakdown of their recent transformation:

I'm Italian.

Everyone asks about underrated Italian villages to move to.

My Dad bought a house in one. Every weekend: €10 truffle pasta photos.

He's living the greatest lifestyle arbitrage opportunity in the world.

Here's his list of 4 Italian villages that are hidden gems: My parents renovated an old house near their hometown.

Not Amalfi Coast. Not Tuscany. In the province of Frosinone (see pic).

I thought they'd lost their minds.

But then I realized I was missing something...

So I asked my Dad for his list of underrated locations across Italy:

I lived in Dubai for 4 years.

Built businesses and helped many relocate there successfully.

I get asked often: "What's the best way to actually move to Dubai in 2025?"

Here are the 3 best pathways:

(Most overlook no. 3 – the best option) 10 years ago, most entrepreneurs had to incorporate a company to get Dubai residency.

Now? Three pathways exist:

1. Digital Nomad Visa
2. Company Formation
3. Freelance License

Let me break down why option 3 is the overlooked opportunity:

This is Ireland:

- 0% tax on foreign income (non-dom regime)
- Only English-speaking EU passport
- EU citizenship in 5 years

One of the most overlooked tax havens in the world.

Here are 8 reasons why "The Emerald Isle" should be on your radar: Ireland went from famine to one of Europe's top financial hubs:

- 1988: "Poorest of the rich" (The Economist)
- 1997: GDP per capita surpassed UK for first time in history
- 2024: Corporate tax revenue hit €39bn (€4.4bn in 2014)

Mr History breaks down the recent transformation:

I'm European.

I recently visited San Francisco and what I saw left me stunned.

Spent my whole life hearing about this city like it was mythical.

But the reality there is...complicated.

Here's the raw truth about San Francisco in 2025:

(An Italian’s perspective) My take:

San Francisco is where America's contradictions concentrate into a brilliant, chaotic mess.

But it's also where the future literally gets built.

After 5 days back here...

8 raw takes on why it's either humanity's greatest opportunity or its strangest experiment:

I'm Italian.

Born in Rome, lived in Dubai for 4 years, built businesses across 3 continents.

You don't realize what you have until you leave it.

Here's the raw truth about Italy in 2025 - the magic, the dysfunction, and why it might be exactly what you need: My honest take:

Italy is where all of Europe's problems concentrate into a majestic, chaotic mess.

But it's also the most beautiful country ever built by human civilization.

2,000+ years of history. Irreplicable.

6 reasons why Italy in 2025 is either your dream or nightmare:

This is Czechia:

- 0% wealth tax
- Up to 50% cheaper than Western Europe
- Birthplace of Trezor wallets & first Bitcoin café

Previously socialist, it's now one of the most libertarian societies in the EU.

Here are 8 reasons why the Czech Republic should be on your radar: First, some context…

Czechia has a fascinating history spanning:

- Medieval Kingdom of Bohemia
- Industrial heart of Austro-Hungarian Empire
- 1989 Velvet Revolution peacefully overthrowing communism

It's become a quietly thriving country that chooses freedom over conformity.

The wealthy don't protest. They exit.

10,800 millionaires left the UK in 2024 - a 157% surge from 2023.

But if you’re leaving and want to match London's infrastructure and have a European lifestyle...

Where do you go?

Here's my realistic list of alternatives in 2025: I've been commenting on this exodus for months…

The UK punished success.

- Non-dom status? Gone from April.
- Capital gains jumped from 20% to 24% overnight.
- Someone earning £5M abroad now pays £2.25M+ in UK taxes.

The impact?..

This is Uruguay:

- 0% tax on foreign income for 11 years
- Permanent residency in just 2 years
- Less corrupt than the US

One of the most underrated countries in the world.

Here are 11 reasons the "Switzerland of South America" is a hidden gem: First, some context!

Uruguay is South America’s 2nd smallest country but has a rich history spanning from:

- The indigenous Charrúa peoples
- Spanish conquests
- Declaration of independence from Brazil in 1825

Since then, it has become a quietly thriving country.
(Great overview here by Mr History)

The rise and fall of Australia:

- One of the world’s richest countries in natural resources
- Biggest household income drop (2024)
- Sydney: 2nd most expensive city globally

From the “Lucky Country” to alarming trends.

Here's a breakdown of what’s happening there and why: Australia was dubbed "the Lucky Country" in 1964, but as a warning.

Author Donald Horne criticized relying on luck:

- Vast resources, minimal innovation
- Geographic isolation from conflict
- "Australia lives on other people's ideas."

But what happens when luck runs out?

This is Singapore vs Dubai:

- Singapore: The billionaire's hub (in flip-flops)
- Dubai: The tax-free oasis (in Lamborghinis)
- Two paths to freedom

I spent 4 years in Dubai, incorporated 2 businesses in Singapore.

Here's my breakdown of who should choose which city (and why): First, a quick background comparison:

🇸🇬 Singapore: Small trading port to global financial hub in decades. Now manages $2T+ in assets.

🇦🇪 Dubai: Humble port town to metropolis in 50 years. Sheikh's vision of a tax-free haven brought to life.

Both have seen incredible rapid growth.

Just landed back in Lisbon from Dubai.

Some cities are for retiring.
Others are built for hyper-growth.

Finding both?
Nearly impossible.

Here are my raw notes from Dubai ’25: 1. 1. Dubai is FAST.

Like, seriously fast.
Deals close in 24h.
Investors commit before you finish the pitch.

Being back after a while, I was reminded of the sheer speed…

This is Taiwan:

- 0% tax on foreign income
- Digital Nomad Visa launched in 2025
- Cost of living ~60% lower than Singapore

It's one of the safest and freest countries in the world.

Here are 7 reasons why “the beautiful island" should be on your radar: First some history:

- Dutch and Spanish colonization in the 1600s
- Qing Dynasty rule (1683-1895)
- Japanese occupation (1895-1945)
- ROC government relocation in 1949

Understandable why it was named Ilha Formosa ("beautiful island"). Mr. History breaks down the early history:

I'm European.

For 30 years, I've lived in various countries across the continent.

I get asked daily:

"Where should I actually move to in Europe?"

Here's a realistic list of countries I'd consider moving to in 2025 and why:🧵 The European reality:

North = Economic engine, efficient systems, but boring and cold

South = Weather, food, quality of life

The Southern lifestyle is THE European dream everyone knows.

Let’s dive into the best options and some other hidden opportunities 👇