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🌍 Transition Planning and Moving


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 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


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


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


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


How Long It Really Takes to Move to Italy
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.
May 66 min read


🐾 Bringing Your Pet to Italy: A No-Nonsense Guide for Dog (and Cat) Parents Planning the Big Move
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.
Apr 304 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


What the F is an Apostille?
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
Apr 173 min read


Visa Maze Walkthrough: Decoding Long-Stay Visas for Your Move to Italy
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
Apr 107 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


How to Avoid the Biggest Mistakes People Make When Moving to Italy
How to avoid the biggest mistakes when moving to Italy.
Mar 204 min read


How to Prepare for Switching Your Digital Life for an Italian Move
How to keep your digital life going in Italy without glitches.
Mar 195 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
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