CaesarTheDay: Retire Abroad. Live Better. - Details, episodes & analysis

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CaesarTheDay: Retire Abroad. Live Better.

Caesar Sedek | Retire Abroad & Italy Relocation

Education

Society & Culture

Frequency: 1 episode/6d. Total Eps: 7

Thinking about retiring abroad or moving to Europe?

CaesarTheDay® is about what it actually takes to make that move work — financially, legally, logistically, and personally.

Hosted by Caesar Sedek, the show explores the real planning behind life abroad: visas and residency, taxes and retirement timing, healthcare, choosing where to live, learning the language, navigating bureaucracy, and figuring out what life looks like after the move.

Italy relocation is a major focus, but the bigger conversation is about building a smarter path from life in the U.S. to life in Europe.

Expect practical advice, personal experience, lessons from Caesar's own relocation planning, and candid conversations about the decisions people often discover too late.

No fantasy version of expat life. No endless shots of Aperol Spritzes pretending bureaucracy doesn't exist.

Just practical planning for people who want to retire abroad and live better.

Learn more, explore the tools, books, relocation resources, and consulting services at CaesarTheDay.com.

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Data updated on 31/10/2026

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https://www.caesartheday.com/guides
7 shares
https://www.caesartheday.com/books
6 shares
https://caesartheday.com
5 shares

https://www.facebook.com/groups/caesarthedayretiretoitaly
6 shares

https://caesartheday.substack.com
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Score global : 68%

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Rent or Buy in Italy? The Math Nobody Shows You

Season 1 · Episode 7

Tuesday, October 27, 2026 • Duration 12:22

Caesar and his wife are moving to Italy in 2030 and they are not buying a house. This episode lays out why: the equity from their California home is the bridge they live on until retirement accounts and Social Security start, the round trip on an Italian apartment costs real money before the market moves at all, and renting keeps them free to follow their daughters wherever those two end up. It also covers how long-term Italian leases actually work, and the cases where buying is the better call.

Key takeaways

Decide what your housing money is for before you decide what to do with it. Spare cash and the money you live on are not the same decision.
A simplified example on a €300,000 main home: roughly €16,000–€18,000 in fees to buy and about €11,000 in agency commission to sell. Close to €30,000 round trip, or nearly two years of rent at €1,300 a month.
The Italian house is not automatically the retirement plan. Istat had existing-home prices about 17% below 2010 levels by 2019, recovering 4.7% last year.
In an Italian rental, extraordinary repairs are generally the landlord’s and ordinary upkeep is yours. Owning means the condo fees, the facade and the boiler are all yours.
The 4+4 lease runs four years then renews for four. The landlord can refuse that first renewal only on statutory grounds, in writing, six months ahead. After eight years they can decline without a reason.
Buying makes sense if you know the town in every season, the money isn’t what you’re living on, and you’re staying put. Get a notary and a geometra involved before you sign.

Sources mentioned

Istat, existing-home price index (via ANSA, July 2019, and the Istat Q4 2025 release)
idealista.it guide to the costs of buying property in Italy (January 2026)
Italian Law 431/1998, articles 2–3, on residential lease types and notice
Agenzia delle Entrate, lease registration

Chapters

0:00 Buying a house in Italy? We’re not
0:41 The House Hunters problem
1:06 Where we are: moving to Italy in 2030
1:26 Our money is a bridge, not a down payment
2:04 Rent vs buy in Italy: the real math
3:55 Kids, flexibility and the 2042 apartment
4:52 “Rent is throwing money away”
5:27 How long-term renting in Italy works
6:46 Our rental must-haves
7:23 When buying in Italy is the right call
8:16 Now, Next, Not Yet

Free Renting In Italy Guide:

Free Renting in Italy guide: contract types, what to check before you sign, and the questions to ask the landlord. https://www.caesartheday.com/guides

Links

CaesarTheDay®: https://www.caesartheday.com
7% Escape Map: https://italy7percent.caesartheday.com
Veni. Vidi. Vici. regional guides: https://italy.caesartheday.com
Books: https://www.caesartheday.com/books

Simplified example only. Fees vary by property, agency and region, and rules change. Not legal or tax advice: get a notary and a geometra involved before you sign anything.

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Can You Get the Italy ERV? What Consulates Really Want.

Season 1 · Episode 6

Tuesday, October 20, 2026 • Duration 15:41

Summary. The Italy retirement visa, officially the elective residency visa, depends on the Italian consulate that covers where you live, which is why every checklist you find online disagrees with the next. Caesar walks through the income test as of January 2026, the seven documents almost every consulate asks for, the Prenot@mi appointment, and how to present the packet in your consulate's order. He ends with a Now, Next, Not Yet plan and a walkthrough of Visto Facile, his own tool (disclosed in the episode).

Key takeaways

Your consulate sets the requirements. Facebook groups, Reddit and old blog posts are each right about their own consulate at the time they applied.
As of January 2026, the consulates Caesar emailed said about €31,000 a year per applicant in dependable passive income, so about €62,000 for a couple. It's a minimum, not a pass mark. Vancouver still used an older formula. Check your consulate.
Consulates assess income, not your bank balance. Work income doesn't count.
Housing in Italy is needed before the consulate says yes. An unregistered lease is a common mistake.
The appointment is the hardest item to get. Slots can disappear in minutes.
Order the packet the way your consulate orders it, make every figure match, and keep it simple.

Official sources mentioned

Your own Italian consulate's published instructions for the elective residency visa (download and date them)
Prenot@mi, the appointment portal
Agenzia delle Entrate, the Italian revenue agency

Start the 14-day free trial of Visto Facile, no card needed: https://vistofacile.caesartheday.com

Links

The Cost of Living in Italy for Retirees: The Real Monthly Budget

Season 1 · Episode 5

Monday, October 12, 2026 • Duration 11:53

Summary

What does it actually cost a retired couple to live in Italy? I walk a fictional couple through six budget lines in three kinds of town, from a small southern town to Rome or Milan, with the arithmetic out loud. Then the setup costs nobody puts in a monthly number, how the elective residency visa's income requirement compares with what you'll really spend, and where his own family's budget lands (hint: the sea view is not cheap).

Key takeaways

A fictional retired couple spends about €2,030 a month in a small southern town, €2,565 in a mid-size city and €3,700 in Rome or Milan, before a cushion, income tax or a car.
Rent is the line that moves. Housing is about 39% of the budget in the small town and 55% in Rome or Milan.
Healthcare doesn't care which town you pick. Voluntary SSN enrollment starts at €2,000 a year and rises with income. One contribution can cover a dependent spouse, but two retirees with their own income may each pay, so ask your ASL whether your spouse counts as a dependent.
Budget the move separately: a deposit (legally capped at three months' rent), registration and fees can run €2,800–€4,700 on a €900 rental.
The ERV's roughly €31,000 per applicant is the ticket in, not your budget. Compare what's left after tax with what you'll spend.
Use the median of five real rentals in one town, not the cheapest listing.

Sources mentioned

Immobiliare.it rental market data, asking rents, August 2026: https://www.immobiliare.it/mercato-immobiliare/
Istat, household consumption survey, 2024 data (published October 2025): https://www.istat.it/comunicato-stampa/spese-per-consumi-delle-famiglie-anno-2024/
Voluntary SSN enrollment minimum: Budget Law 213/2023 (Legge di Bilancio 2024), art. 1, paras. 240–241. Contribution formula and dependents: ASL Città di Torino and ASL CN1 Cuneo voluntary enrollment forms

Where to Retire in Italy: The 5 Filters That Matter

Season 1 · Episode 4

Tuesday, October 6, 2026 • Duration 17:28

I built a map of 2,528 Italian towns that can qualify for the 7% tax regime, then my family picked a region that isn't on it. This episode is the order of decisions we used to choose where to retire in Italy, and where the 7% belongs in that order.

Summary. Choosing where to retire in Italy is a series of eliminations, and the order matters. The five filters are the care radius, family gravity, the no-car test, the life you actually live, and only then the money, including the 7%. Caesar walks through a fictional couple, Tom and Lisa, to show how a cheaper town in a 7% region can cost more by year eleven.

Key takeaways

A town has to work for you at 78, not only at 65. You are choosing for twenty years or more.
Pick your emergency-department number before you open a single listing: the most minutes you will accept to the nearest pronto soccorso.
Count family distance door to door, in hours and connections, not in kilometers.
A train station is a building. A service is a train that arrives when you need it. Check Sundays and evenings.
The 7% is a way to compare towns that already passed the first four filters. It is not a reason to choose one, and it lasts up to ten tax years.
Now, Next, Not Yet: write down three numbers, run the free Escape Map quiz against them, and stay off the real-estate sites for now.

Sources and facts mentioned. Law 34/2026 (7% regime now covers municipalities up to 30,000 inhabitants, effective April 7, 2026). The regime requires qualifying foreign pension income and no Italian tax residence in the prior five years. U.S. citizens still file U.S. returns and may owe U.S. tax. Tom and Lisa are fictional and their numbers are examples, not a forecast.

Do this next. Take the free quiz on the 7% Escape Map. It gives you ten matched towns, and you don't need Pro for it. Run each one through your three numbers: https://italy7percent.caesartheday.com

Retiring in Italy: Your Five-Year Financial Roadmap

Season 1 · Episode 3

Sunday, October 4, 2026 • Duration 18:46

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 five-year financial roadmap: understanding your accounts, building a realistic budget, turning savings into income, and preparing for the costs and paperwork that continue after you arrive.

Simple examples, plain English, and a little humor. No accounting degree required.

YOUR FIVE-YEAR ROADMAP

Five years out: Take inventory of your retirement accounts, savings, pensions, and future Social Security. Identify your visa route and the income you’ll need to document.
Four years out: Price everyday life—including healthcare, flights home, and occasional expenses. Keep moving costs separate from your regular budget.
Three years out: Build your retirement paycheck. Cover the gap before pensions or Social Security begin, and examine taxes, Roth conversions, and Italy’s seven-percent program.
Two years out: Test the plan against a weaker dollar and disappointing investment returns. Spend time in the towns you’re considering and see what ordinary life actually costs.
The final year: Confirm account access, money transfers, healthcare, and the documents you’ll need for your residence permit and renewals.

THE VISA NUMBER ISN’T YOUR LIVING BUDGET

We discuss the roughly €31,000 in annual financial resources per applicant referenced in U.S. consular elective residence visa guidance—roughly €62,000 for two applicants. Boston specifies more than €31,000 per person.

Meeting that figure doesn’t guarantee approval. The source and reliability of your income matter, and the ERV does not permit work. Check the consulate serving your home address.

We also briefly cover the digital nomad route and why you’ll need to keep documenting financial support when renewing your , or residence permit.

Retiring Abroad: I'm Four Years Out — Here's What I'm Doing Now

Season 1 · Episode 2

Thursday, September 24, 2026 • Duration 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 deliberately not doing yet, and why timing matters so much when you’re planning a move abroad.

We’ll talk about the financial runway before retirement, tax planning, Roth conversions, language learning, location research, scouting trips, healthcare, residency, and the difference between understanding the process now and collecting documents too early.

I’ll also get into the personal side of the decision: why I’m leaving, what I want life to look like after the move, and why this is less about “escaping” America and more about designing the next phase intentionally.

If you’re a few years away from your own move to Italy or elsewhere in Europe, this episode is about using that time wisely.

Resources:
CaesarTheDay® — https://caesartheday.com
Escape Map 7% — https://italy7percent.caesartheday.com
Visto Facile — https://vistofacile.caesartheday.com
Books — https://caesartheday.com/books

CaesarTheDay® — Retire Abroad. Live Better.

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Planning Your Move to Italy: You’re Starting Later Than You Think

Season 1 · Episode 1

Wednesday, September 23, 2026 • Duration 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 begin years earlier. From taxes, retirement timing, Roth conversions, and healthcare to language, location, housing, and the emotional side of leaving the life you already know, there are multiple clocks running at once.

You’ll also hear why choosing a town as a resident is very different from choosing one as a tourist, why learning Italian needs to start earlier than most people think, and why collecting documents too soon can be just as unhelpful as starting too late.

If Italy is part of your next chapter, this episode is about getting the order right.

Learn more at CaesarTheDay.com

CaesarTheDay® — Retire Abroad. Live Better.

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CaesarTheDay: Retire Abroad. Live Better. - Details, episodes & analysis

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