🛠️ Tips & Resources

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...

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.

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.

Picture this: your plane wheels screech against the tarmac at Malpensa. The flight attendants are still yelling at everyone to sit the...

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.

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.

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...

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).

Everyone wants the fantasy — sell the house, hop a flight, sip espresso on a terrace in Italy. But the reality? Moving abroad takes more than daydreams and a passport. This guide breaks down the real timeline it takes to move to Italy — from financial prep and scouting trips to Roth conversions, visa chaos, and post-arrival bureaucracy. If you’re planning your escape, this is where the real work starts.

Thinking of bringing your dog or cat to Italy? Don’t wing it — the EU pet rules aren’t forgiving. This guide walks you through every step: microchips, vet visits, USDA forms, flights, and what happens when you land. Based on real experience (with a 90-pound Bernedoodle in tow), this is the no-fluff, all-facts plan for a smooth relocation — and a happier pet.

Thinking about renting or buying in Italy? Before you fall for the Instagram daydream, you need to hear the reality most guides won’t tell you. From shady leases to crumbling villas with ‘for sale’ signs older than you are, this is the brutally honest roadmap to surviving Italy’s real estate jungle — and making smart decisions without losing your mind (or your money).

If you’re applying for a visa to Italy (or basically doing anything official across borders), you’ll run into this mysterious word: apostille. It’s not a pasta. It’s not a neighborhood in Florence. It’s a bureaucratic stamp of approval that tells a foreign government your documents are legit. In this post, I break down what it is, when you need it, and how not to screw it up — because nothing says welcome to Italy like your FBI background check being rejected over a missing s

Retiring in Italy? Start here. This first CaesarTheDay newsletter dives deep into Liguria—real towns, real prices, and why we chose it over the usual postcard fantasies. You’ll get city-by-city breakdowns, healthcare insights, and tips on cutting U.S. state tax ties (especially if California still wants your money). It’s free, honest, and packed with what actually matters when planning your escape.

Thinking of retiring or relocating to Italy? Before you start picturing aperitivo hours and rolling hills, you’ll need to face Italy’s most stubborn gatekeeper: the visa system. This post breaks down every major long-stay visa option—from the Elective Residency Visa to the brand-new Digital Nomad Visa—with real talk, real requirements, and zero sugarcoating. If you’ve been overwhelmed by consulate websites, expat forums, or conflicting advice, this is the clear, detailed walk

A no-fluff breakdown of Italy’s 7% flat tax vs. U.S. retirement costs—real math, smart strategy, and what happens after year 10.

Everything you need to know about applying for the Elective Residency Visa (ERV) to Italy. Checklist Included!

How to keep your digital life going in Italy without glitches.

Leaving the U.S. Behind & Embracing a New Future in Italy When I came to the U.S. as a teenager, I believed I was stepping into the...