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


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


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


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


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


Renting vs. Buying in Italy
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).
Apr 269 min read


Why We’re Leaving the U.S. for Italy: A Family’s Story of Burnout, Planning, and Purpose
We didn’t have a single “we’re moving to Italy” moment. No dramatic speech. Just a slow unraveling of the American dream—burnout, layoffs, active shooter drills, and a creeping sense that this system no longer serves us or our kids. So we made a plan. Not an escape, but an intentional departure. This isn’t just my dream. It’s our family’s next chapter—built together, on purpose.
Apr 188 min read


Retiring Smart: U.S. vs. Italy (7% Flat Tax Scheme vs. Progressive Tax)
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.
Apr 415 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


Elective Residency Visa (ERV): The Ultimate Document Checklist Before You Say “Ciao” for Good
Everything you need to know about applying for the Elective Residency Visa (ERV) to Italy. Checklist Included!
Mar 286 min read


Finding a Home in Italy: How We Chose Where to Live
How we found our corner of paradise on Earth in Italy. What factors matter, what speaks to you, what feel "right."
Mar 205 min read


Why Italy, Why Now?
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...
Mar 177 min read
bottom of page