top of page

CAESAR THE DAY
Search


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


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


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


Veni | Vidi | Vici Newsletter #1: Liguria Region Breakdown + Tips on Breaking State Tax Ties
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.
Apr 162 min read


Italy’s 7% Flat Tax for Retirees: What’s Real, What’s BS, and What You Actually Need to Know
Italy’s 7% tax deal for retirees sounds amazing—but most advice online is dubious. Here’s what’s real, what’s BS, and how to qualify.
Mar 305 min read


How to Choose the Ideal Italian Location for Your Move
How to decide where in Italy you should call home.
Mar 185 min read
bottom of page