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Borderless Wealth: How to Think (and Invest) Like a European
The first time I walked into an Italian bank, I thought I’d made a wrong turn and ended up in a museum. The marble counters were chipped from the 1960s, the chairs squeaked, and the teller—an older man with a mustache that looked unionized—stamped my form with a satisfying thud that echoed through the room like a declaration of independence. No rush. No digital screens counting my impatience. Just the rhythm of a man who has never once said the words “time is money.” And that
5 days ago5 min read


The Death of Crowdsourcing (and Why I Built My Own Tools Instead)
My not-so-gentle manifesto on Facebook advice, AI regurgitation, and why I’d rather build than bullshit. For the past year I’ve been...
Oct 14 min read


The Quest for the Perfect Place to Live: A Journey Through Imperfections
There is no perfect country — only different imperfections arranged in new ways. From U.S. burnout to European bureaucracy, here’s a candid look at what it really means to retire abroad, why politics sting less when you can’t vote, and how to decide which flaws you’re willing to live with.
Sep 254 min read


The 7% Flat Tax in Italy: What It Really Means for Retirees
The 7% flat tax in Italy sounds simple — pay 7% on your pension income and live happily ever after. But once you dig into the details, the picture gets a lot messier. Social Security, IRAs, private pensions, annuities, government pensions, VA benefits, and Roth IRAs are all treated differently under the U.S.–Italy tax treaty.
Sep 156 min read


Facebook Wisdom and the Great Italian Treasure Hunt
Tired of noisy expat Facebook advice? Discover why one-liner opinions won’t help you decide where to live in Italy, and how CaesarTheDay offers real strategies, context, and a growing community focused on clarity and expertise.
Sep 23 min read


The First 90 Days in Italy: A Survival Guide for the Newly Arrived (a.k.a. How Not to Lose Your Mind or Get Deported)
Picture this: your plane wheels screech against the tarmac at Malpensa. The flight attendants are still yelling at everyone to sit the...
Sep 14 min read


House Hunting in Puglia: A Scouting Trip with Backup on Speed Dial
Retire in Puglia? Discover how a scouting trip to Ceglie Messapica—with Ostuni, Martina Franca & Cisternino as options—helped a couple plan with clarity.
Aug 234 min read


Italy vs. Portugal vs. Spain vs. France: Who Wins the Retirement Hunger Games?
Thinking of retiring in Europe? Compare Italy, Portugal, Spain, and France on cost, healthcare, taxes, and lifestyle to find your best fit.
Aug 204 min read


Beyond ERV: Why the Italy Investor Visa Should Be on Your Radar
Explore Italy’s Investor Visa as an alternative to the ERV. Learn requirements, process, pros/cons, and how it can lead to residency in Italy.
Aug 196 min read


You Made It to Italy - Now What?
How to apply for the Permesso di Soggiorno, Tessera Sanitaria, set up banking, and get your life started in Italy as an ERV visa holder.
Aug 55 min read


Do You Need an Italian Bank Account - Or Is Wise Enough?
Thinking of retiring or relocating to Italy? Here’s when a Wise or Revolut account is enough — and when you’ll need to bite the bullet and open a real Italian bank account. We compare fees, IBANs, utilities, and bureaucracy-proofing your finances.
Aug 13 min read


10 American Luxuries You’ll Mourn—And Why That’s Okay
Moving to Italy? Discover the 10 absurd American comforts you’ll miss—and the quirky Italian perks that might just win you over.
Jul 236 min read


Codice Fiscale: Italy’s Social Security Number, Sort Of — and Why You’ll Need It Before You Even Move
Before you can rent an apartment, open a bank account, or register with the Italian health system, you’ll need a Codice Fiscale — Italy’s version of a Social Security Number. This post breaks down what it is, why you need it, and how to get one before you even move. Whether you’re applying for a visa, securing a long-term lease, or just trying to open a wine club membership, this little code matters more than you think.
Jul 113 min read


One Town, Three Lenses
How do solo retirees, remote workers, and couples with pets experience the same Italian town differently? This guide explores the practical realities of life abroad through three unique lenses — helping you choose the right place for your version of la dolce vita.
Jul 75 min read


Scouting Italy: What to Look for (Beyond the Gelato and Piazza Vibe)
You’re not just touring. You’re test-driving your future life. So here’s what actually matters. There’s a seductive rhythm to Italian...
Jun 297 min read


Renting in Italy: Red Flags and Green Lights
Renting in Italy can be a dream — or a bureaucratic, mold-infested nightmare. This guide breaks down everything you need to know to evaluate a long-term rental, including contract types, heating systems, energy ratings, and internet access. If you’re scouting, applying for a visa, or planning your escape from the U.S., this checklist could save your wallet (and your sanity).
Jun 265 min read


New Book Alert: Greener Pastures Is Here — And It Might Just Change Your Exit Strategy
What if Italy isn’t the only answer? Greener Pastures is the new no-BS guide to retiring in Europe — with side-by-side comparisons of Italy, Portugal, Spain, and France. Inside: clear timelines, real cost breakdowns, tax strategies, healthcare comparisons, and everything U.S. expats need to plan a smart escape.
Jun 233 min read


What $200k Really Buys You in Italy’s 7% Towns
Thinking of retiring to Italy under the 7% flat tax? Here’s what $200,000 can actually buy you in walkable small towns—from restored homes in Puglia to fixer-uppers in Le Marche. Real listings, real advice, no sugarcoating.
Jun 105 min read


Why Cutting State Tax Ties Matters (Even If You’re Leaving the U.S.)
Think moving abroad means you’re done paying U.S. state taxes? Think again.
If you’re leaving California, New York, or another high-tax state, you need more than a plane ticket—you need a paper trail that proves you’re gone for good. From surrendering your driver’s license to scrubbing your digital footprint, this guide breaks down how to legally and permanently cut tax ties before you move abroad.
Jun 37 min read


Understanding Italy's Taxation on U.S. Retirement Accounts
If you’re retiring in Italy with U.S. retirement accounts, read this first. Learn how Italy taxes IRAs, Roth IRAs, and 401(k)s, how the U.S.-Italy tax treaty works, and what to expect under Italy’s progressive and 7% flat tax regimes.
May 203 min read
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