How Long It Really Takes to Move to Italy

A Real Timeline, Real Delays, and the Real Work No One Tells You About

Everyone loves a good Italy daydream: sell the house, hop a flight, and start your new life sipping espresso on a sunlit terrace. But if you’re planning an actual move — not just a sabbatical or long vacation — a real, permanent relocation — you need more than a suitcase and a fantasy.

You need time. And not the curated Instagram kind.

Most guides start with paperwork. I’m not most guides.

Because the decision to move abroad — especially if you’re planning to retire in Italy — doesn’t start with documents. It starts with your life. Your money, your obligations, your values, and your vision for what this next chapter is actually supposed to be.

If you’re here to understand how long it really takes to move to Italy, this is your timeline.

Not the “two months to sell everything” fantasy — the real, boots-on-the-ground, wine-in-hand, crying-in-the-questura truth.

Want the full tactical plan? It’s all in my book:

Escape Plan: How to Move from the U.S. to Italy Without Losing Your Mind or Money

The Real Timeline: From First Thoughts to Full Residency

This isn’t a checklist. It’s a multi-year strategy. For most people, you’ll need 2–4 years of planning — especially if you’re doing this thoughtfully and legally. Here’s what that really looks like.

36–30 Months Out: Reassessment Mode

This is the phase most people skip — and then regret skipping later.

What to Do:

• Audit your life. Where are you tied down — emotionally, financially, logistically?

• Ask the hard questions. Are you escaping something or building something? Do you want slower living or just different scenery?

• Model your retirement. Can you actually afford to stop working early? What income will support you abroad — IRA withdrawals, rental income, Social Security?

• Meet with a fiduciary financial advisor who understands expat living, not just U.S.-based retirement math.

• Start Roth conversions if you’re in a low tax bracket now. Roth money is extremely powerful once you’re living in a higher-tax country.

• If you’re serious, take your first scouting trip. Don’t just sightsee. Investigate livability, walkability, cost, access to healthcare, infrastructure, noise, and culture fit.

  • If you're able - make it a full 90 days tryout. Spend time in one or two places that you believe may tick most of the boxes:

  • These people are doing it right. Marty and Paula are TryingOnItaly and sharing their adventure on their blog - check it out!

24 Months Out: Decision and Direction

Time to move from dream to direction.

What to Do:

• Commit to a timeline. Decide if this is a 2-year, 3-year, or 5-year move and stick it somewhere visible.

• Choose your visa path. Elective Residency Visa (ERV), citizenship by descent, or another legal route. Don’t rely on wishful thinking — verify that you’re eligible.

  • With recent changes to the citizenship route, many people are no longer eligible, and consulates are innundated potentially extending the application process.

• Start minimizing your U.S. footprint. Consolidate financial accounts. Cancel or streamline subscriptions. Begin planning an exit from your high-tax state.

• Begin purging stuff. Sell, donate, digitize. Every closet you clean now will save you panic later.

• Research 7% tax towns if you qualify. This could massively lower your Italian income tax burden for ten years.

18 Months Out: Bureaucracy Warm-Up

Welcome to the slow grind of Italian admin — which, weirdly, starts in America.

What to Do:

• Order long-form birth and marriage certificates (with raised seals). Get them from every relevant state or country.

• Research apostille and translation requirements for your visa documents. Start early — timelines vary by state.

• Deep-dive your consulate’s visa process. No two are the same. Print out requirements and track updates.

• Audit your income. Does it meet the ERV threshold? Is it truly passive? Can you document it properly?

• Talk to an expat tax advisor. Understand how to position your income, how the U.S.-Italy tax treaty works, and how to avoid double taxation.

• Begin preparing your exit strategy from your current state, especially if it’s California, New York, or another aggressive tax jurisdiction.

12 Months Out: Paperwork Phase

Now you’re on the clock. Everything starts to get very real.

What to Do:

• Secure housing in Italy. Most consulates require a one-year lease or property deed before you can apply.

• Prepare your visa packet. Include:

  • Proof of passive income

  • International health insurance

  • Notarized letter of intent

  • Apostilled and translated documents

  • Bank letters and balances

  • Copies of your passport

  
  

• Schedule your consulate appointment. Some require booking months in advance — others only open appointment windows 30–90 days out.

• Prepare your pet. Italy requires a microchip, rabies vaccine, and EU health certificate — all timed precisely.

• Choose your health insurance. Make sure it’s valid for ERV requirements and covers the full first year.

9 to 6 Months Out: Submission and Waiting

This is where things feel suspended — you’ve done your part, now you wait.

What to Do:

• Submit your visa application.

• Keep backups of all documents, both digitally and on paper.

• If you’re eligible, consider starting the process of getting an EU driver’s license (Polish, in your case) while still in the U.S.

6 to 3 Months Out: U.S. Logistics Ramp-Up

Assuming your visa is processing or approved, this is the practical phase.

What to Do:

• Put your house on the market, prepare it for rental, or line up long-term storage.

• Sell everything you don’t want to ship. Don’t overestimate how much you’ll want to bring.

• Get quotes from international movers — or go full minimalist and plan to buy in Italy.

• Set up a virtual mailbox (e.g. Traveling Mailbox, Anytime Mailbox) to manage U.S. mail once you’re gone.

• Notify all U.S. institutions — banks, Social Security, tax prep software, etc. — of your international move.

• Execute your state tax exit plan.

3 to 1 Month Out: Launch Mode

You’re down to final logistics, emotions, and a thousand tiny loose ends.

What to Do:

• Book your flights (ideally refundable).

• Pack documents: originals, certified copies, and digital backups.

• Organize medication, power adapters, unlocked phone, SIM cards.

• Get your International Driver’s Permit. AAA can issue it in the U.S., and you’ll need it to legally drive in Italy and it's valid for a year. Then you'll need the Italian DL.

• Finalize any prescriptions and get records from your doctor.

• Say your goodbyes. Celebrate, mourn, reflect. This is real now.

After Arrival: Italian Bureaucracy Begins

The visa gets you into Italy. Residency makes you legal.

What to Do:

• Within 8 days, file for your permesso di soggiorno (residence permit).

• Register with your local comune as a resident.

• Apply for your Tessera Sanitaria (regional health card).

• Get your Carta d’Identità (ID card).

• If you don’t have one yet, get your Codice Fiscale (Italian tax code).

  
  

All of this can take weeks or months. Bring patience. And a sense of humor.

Before You Pack: A Note About Escape

Look, I cheekily titled my book Escape Plan because it captured how this all started for me. I was fed up — with the cost of healthcare, the state of politics, the burnout culture, the creeping sense of dread. I wanted out.

But moving to Italy won’t fix your life.

It won’t save your marriage.

It won’t erase anxiety or career regret or loneliness.

Geography doesn’t heal wounds. It just gives you new scenery while you unpack them.

So before you go all-in on this dream, make sure it’s not just about escape. Make sure you’re not just running. Because if you don’t face those demons now, they’ll follow you — and they’ll still be there after your cappuccino.

Move toward something. Build something. Don’t just evacuate.

And if that’s what you’re already doing? You’re on the right path.

Bottom Line

This move isn’t a two-month packing sprint. It’s a two-to-four-year lifestyle transition. One that starts with asking better questions, then slowly — methodically — building the next version of your life.

It’s not easy. It’s not fast. But it is absolutely, completely worth it.

---

Want the full roadmap?

I wrote Escape Plan to give you the strategy, not just the story. Inside, you’ll get:

• A full 24-month countdown planner

• Financial modeling tips for expats and retirees

• A complete ERV visa checklist

• And with the site membership, downloadable Notion dashboards, tax town maps, and more

Get the book here: Escape Plan

Grab the full ERV tracker inside the Resources tab at CaesarTheDay.com

🛠 How to Use This Tracker

To get started, you’ll need a free Notion account (if you don’t already have one, you can sign up at notion.so).

Once you click the button above, you’ll be taken to the CaesarTheDay ERV Tracker. In the top-right corner of the page, click “Duplicate” to add it to your own Notion workspace.

You’ll then be able to:

• Customize tasks for solo or couple applications

• Track your documents, income proof, and consulate deadlines

• Use pre-filled templates for your cover letter and emails

• Add your own notes, links, and files

⚠️ Important: This is a self-service planning tool, not legal advice. Always check with your assigned consulate for current requirements and timelines.

🆕 New to Notion? No problem

1. Click the button above to open the ERV Tracker

2. In the top-right corner, click the “Duplicate” button

3. If you don’t have a Notion account yet, you’ll be prompted to sign up for free

Once duplicated, the tracker is yours to edit. You can update checklist items, add documents, or tweak it for your personal situation.