People love the fantasy of retiring abroad: two people strolling through narrow streets, coffee cups clinking on a sunlit table, life finally slowing down to the rhythm they always wanted. And yes, some parts of that are real. But the thing no glossy article says — the thing I’ve started thinking about more and more when I talk to couples planning their move to Italy — is that a relocation this big doesn’t magically strengthen a marriage. It magnifies it. When you remove the

I thought I knew Italy from summers, Rome, and traveling the country—then these books showed me whole new sides: the chaos, the humor, the real daily life most of us never see. They made Italy feel bigger, more human, and—without meaning to—turned my “someday” into an actual plan.

Retiring in Italy is more than visas and logistics. This piece explores the deeper truth of aging abroad, what happens when life takes an unexpected turn, and how to build a community that actually holds you when you need it.

Italy is beautiful — and sometimes maddening. After a lifetime of travel here, I’ve learned to love the chaos along with the charm. This isn’t a takedown. It’s a collection of sharp truths, from radiators-as-dryers to the eternal cigarette next to your Aperol. Consider this a love letter written in bureaucratic ink and secondhand smoke.

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.

Forget cappuccino rules & influencer traps. Real Italy starts when you slow down, look up, eat local & skip the TikTok checklist.

Italy isn’t a polished lifestyle product. It’s a living, breathing culture—and cultures come with contradictions.

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...