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The CaesarTheDay YouTube channel and podcast: the move to Italy, out loud. Visas, taxes, retirement accounts and real timelines.
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The Move, Out Loud.
Videos and podcast episodes on actually moving to Italy — my own timeline, what I'm doing and skipping, visas, taxes, retirement accounts, and the decisions that don't fit in a checklist.
Latest Videos
Retiring in Italy? Build This 5-Year Financial Plan First
Retiring in Italy isn't just about whether you have enough money. The five years around retirement can determine how you handle taxes, withdrawals, Roth conversions and the move itself. https://caesartheday.com In Episode 3 of CaesarTheDay, we build a…
The CaesarTheDay Podcast
Retiring in Italy: Your Five-Year Financial Roadmap
October 1, 2026 · 00:17:05
Thinking about retiring in Italy in the next five years? Before an apartment with a terrace makes all your financial decisions for you, let’s work out how you’ll pay for the life attached to it. In Episode 3 of CaesarTheDay , we walk through a practical…
I'm Four Years From Leaving America - Here's What I'm Doing Now
September 24, 2026 · 00:22:18
I’m about four years away from leaving the U.S. and building the next chapter of my life in Europe, most likely Italy. So what does planning actually look like this far out? In this episode, I walk through what I’m actively working on now, what I’m…
You’re Starting Later Than You Think: Planning Your Move to Italy
September 23, 2026 · 00:13:31
If you’re three, four, or five years away from moving to Italy, the move has probably already started — whether you realize it or not. In this first episode, Caesar explains why the visa should not be the starting point, and why the bigger decisions often…
Prefer Your Roadmap in Writing?
Books, tools, and one-on-one planning that turn the conversations here into a step-by-step plan.
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