A framework for staying legal, managing money across two countries, staying connected, and building income that travels with you.
You don't have to choose. You can live in America and Italy — not as a fantasy, but as a reproducible system.
The core principle: Americans with a U.S. passport get 90 days visa-free in the Schengen Zone (which includes Italy). You can spend those 90 days anywhere in Schengen, return to the U.S. or visit a non-Schengen country like Morocco or Turkey for 90 days, then come back for another 90-day window. Perfectly legal. No special visa required. Repeat this pattern as long as you want.
We call it the Schengen Shuffle.
Here's how it works in practice:
The immigration officers at Fiumicino don't care why you're there. They stamp your passport. You have 90 days. Use them.
We (Pamela and Garry) both have dual citizenship — American and Italian. That changes the equation.
With an Italian passport, you're an EU citizen. You can spend up to 6 months per year in Italy without visa stress. No Schengen Shuffle. No exit/re-entry dance. You're legal simply by being a resident of an EU member state. Half the year in Italy, half in America, on repeat.
Many Americans don't know they qualify for dual citizenship through family trees — a grandparent, a parent, even a great-grandparent who was Italian at the right time. It's worth exploring. The process is bureaucratic and takes time, but the payoff is significant: you unlock the ability to design a truly flexible split-year life without visa anxiety.
We recommend testing the idea before committing infrastructure. Use those first 90 days to answer real questions:
Many expats spend a year or two on the Schengen Shuffle just to answer these questions. There's no rush to commit to a 1-year lease, dual citizenship paperwork, or a permanent move. The Schengen rules give you the freedom to experiment.
Living in two countries means navigating two financial systems. Money moves slower across borders than you expect. Exchange rates swing. Tax rules overlap. You need a system, not just luck.
Forget your bank's wire transfer. They'll charge you 2–3% in hidden spreads and take 4–7 days to settle. Use Wise.
Wise gives you:
Open a Wise account from the U.S., connect it to your U.S. bank, and set up your Italian account (or use their IBAN if your Italian bank doesn't accept international transfers smoothly).
Don't move all your money when the rate is bad. Use Wise's limit orders to automate the decision:
We use TradingView and Fibonacci retracements to identify likely support levels for EUR/USD, set limit orders there, and let the market come to us. It feels like overkill for people who only transfer once. For people rotating between two countries, it's the difference between feeling like you're constantly losing money and knowing you're getting fair rates.
Don't nickel-and-dime with monthly transfers. The fee math is terrible. Instead:
This approach also minimizes currency fluctuation risk. You're not exposed to the exchange rate for the next 12 months; you've locked it in on the day you transferred.
The U.S. taxes citizens on worldwide income regardless of where they live. But the tax resident status matters for Italian purposes.
To stay a U.S. tax resident:
If you do this, Italy generally won't claim you as a tax resident either. You'll file U.S. taxes on your worldwide income (including income earned in Italy) and claim any Italian taxes paid as a foreign tax credit. No double taxation; the treaty handles it.
If you become an Italian tax resident (180+ days in Italy, or other factors like owning property, family ties, center of economic interest), consult an international tax accountant immediately. The U.S.-Italy tax treaty prevents double taxation, but you'll need professional guidance on reporting, filing deadlines, and coordinating filings in two countries.
As a U.S. visitor (not a Schengen resident), you can claim a VAT refund on purchases over €150 made in Italy within the 90-day window. At checkout, ask for a tax-free form. When you leave Italy, you'll have the receipts stamped at the airport or port, then claim a refund (usually 12–15% of the purchase price). It's not life-changing, but it offsets shopping costs for large purchases.
You need an American phone number, Italian data, reliable internet for work, and a way to receive mail from the U.S. You also need to be present enough in your U.S. home (if you own one) to keep it secure and functional.
Google Fi keeps your U.S. number active in 200+ countries, including Italy. For the first 1–2 months in Italy, use Google Fi. It works. You can make calls, send texts, use data. But after 2 months, Google Fi throttles your data speeds significantly — you'll notice it, especially if you're trying to work.
The solution: Dual SIM.
You now have U.S. reachability and Italian speed. If you're on a Zoom call, you're on Italian data. If someone calls your U.S. number, it rings through Google Fi.
If you're working remotely, internet reliability matters more than your phone.
Always test internet speed at a potential rental during your first visit. Not all Italy moves at broadband speed.
Italy has co-working spaces in most towns. WeWork, Impact Hub, local indie spaces. Use them for focus work and Zoom calls.
Reality check: Most Italian co-working spaces close by 7:30 PM. If you're managing U.S. time zone calls (especially West Coast), you'll be working very early mornings (5–8 AM) or late evenings (after 7:30 PM). Many spaces also close for holidays, August, and random days. Plan accordingly.
For regular afternoon Zoom calls with U.S. teams, many Ameritalians work from a quiet café with good coffee and a power outlet. Bring headphones. Respect the café. Tip well.
You're not physically in America to collect bills, tax documents, or packages. Use a virtual mailbox service:
If you own a home in the U.S., you need to manage it remotely while you're in Italy for 6+ months at a time.
It took us months of trial and error to get this right. Expect to set up automations, fail, adjust, and iterate. It's worth it.
The Ameritalian™ lifestyle is affordable, but not because Italy is cheap. It's affordable because you're designed to live well, not to maximize savings.
You're not moving to Italy to save money. You're moving to live better.
It depends entirely on where you live and how you live. Use Numbeo.com to compare costs in specific cities.
We live in Ferrara — a Renaissance city in Emilia-Romagna, about 90 km north of Bologna. It checks every box:
Ferrara isn't famous like Florence or Venice. It doesn't have the prestige markup. But it's beautifully preserved, culturally rich, and genuinely livable for people actually building lives there, not just visiting.
Some expats obsess over budget — €300/month villages, eating €1 pasta, taking the cheapest flights. They're leaving money on the table in comfort, sanity, and opportunity.
The Ameritalian™ mindset is different. You have American income (or revenue). You're arbitraging that income to live better, not to spend less. Choose a city where you actually want to spend time. Choose an apartment that doesn't feel like a compromise. Choose restaurants where you enjoy being. The money you save by living in Italy (compared to New York or San Francisco) should buy you quality, not just maximum savings.
The critical constraint of the split-year life isn't visas or money transfer. It's income. You need work that doesn't require you to be in an office in New York, San Francisco, or Chicago.
We learned this the hard way.
I (Garry) built and ran an online business, The Paperless Agent, while we were in Italy. The business made money. It was automated. It should have been location-independent.
But it wasn't, because I hadn't designed it to be.
Problems I faced:
The business survived, but it required a lot of friction. If I'd designed it for location independence from the start — with async customer communication, video-on-demand content, timezone-agnostic support, and seamless international payments — it would have been effortless.
Pamela (co-founder) started with local coaching — one-on-one sessions with clients in-person or on Zoom. Location-independent on paper, but the time zone problem was the same as mine.
She pivoted to building a digital community and creating content that scales: email, video, group coaching within set time windows, and async community spaces. This model:
She's now running a global community while living in Italy, working 20–30 hours per week instead of 50+.
Build these into your income design from day one:
It took us a full year of living in Italy before we had a working infrastructure:
This isn't instant. It required:
But on the other side of those months? Freedom. Real freedom.
Finding the right home in Italy is not about price. It's about fit. About location. About understanding neighborhoods. About knowing the right people. That's exactly what we cover in La Tua Casa—the live training that teaches you how to navigate the Italian housing market like an insider.
Whether you're renting your first apartment in Rome or negotiating a purchase in Tuscany, you'll have a clear framework for making the decision that fits your life—not the fantasy.
Our Andiamo™ community has saved over €150K collectively by applying these principles. You don't have to learn this the expensive way.
ENROLL IN OUR NEXT WEBINAR →— Garry & Pamela, The Ameritalians™