Italy looks perfect on paper — the food, the lifestyle, even the 7% flat tax.
But living somewhere is different than visiting it.
After building a life abroad in Portugal, we spent six weeks living in Southern Italy and Sicily to see what daily life is really like. Not a vacation. Real routines, housing, driving, taxes, and bureaucracy.
In this video, we share what we learned by staying long enough to stop being impressed — including the truth about Italy’s 7% tax, passive vs active income, Social Security taxes, and what life feels like in places like Naples, Palermo, Cefalù, Taormina, and Aci Castello.
Italy can be amazing — if you choose it for the right reasons.
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46 Comments
The "It'll Be Fun" Mission & Italy Scouting Update
Welcome to the community! If you’re new here, let me give you the lay of the land. We are a family that moved to Portugal 4 years ago, and honestly, we’ve never looked back—we absolutely love it here.
Who We Are
This channel is a true family effort, and we’re grateful for the time it lets us spend together:
Wolf: Our 25-year-old son is the creative engine and the architect of our financial success. He builds the channel, handles all filming/editing, and manages our investments and daily trades. Lately, he’s been stepping in front of the mic for voiceovers while Alan manages some health issues. He takes care of us as much as we have taken care of him—the tide turns, as we all know.
Leslie: I am the architect of our stories, writing the scripts and managing the business while working daily with Wolf on our investment strategy.
Alan: The voice you’ve come to know and love on the channel.
Our Goal & Mission
Our goal is to let people know you don't have to be a millionaire to build the wonderful life of your dreams. For Alan and Leslie, it was about figuring out how to retire with a minimal amount of money and seeing the world. We are big into creating generational wealth to stop the "no work-life balance" grind we had in America. This move allowed us to invest and trade to secure our future, and Wolf is the one leading that charge.
Italy Scouting Update –
Bom dia! We recently spent six weeks in Southern Italy and Sicily—traveling from Palermo and Cefalù to the slopes of Mt. Etna. Our goal was to stay long enough to "stop being impressed." For us, that is the ultimate test: seeing a place from a real-life perspective rather than through the lens of a vacation. That shift changed how we think about the reality of taxes, the 7% retiree tax zones we scouted, and the daily grind of life there. We’ve seen the beauty, but we’ve also seen the "hard" parts. It’s all part of the homework we do so we can build a life with our eyes wide open. We can't wait to head North next!
Join the Conversation
If you’re considering Italy, Portugal, or anywhere else in Europe, ask your questions below.
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We should have done this sooner.
I have lived in north-east Italy for 56 years and I have always been happy.
Fuck you Americanos why dont you just go to your trump planet ,sick of your stupidity ,did not even get to thev half of the video…
Yeah, thought this might be an okay video to watch but it was inaccurate and felt like a typical attitude of 'using' rather than asking oneself, 'what can I bring?'. Those broad assumptions and generalisations about houses and renovations etc. are just that, generalisations that are mostly not true. You are missing out on something special with this attitude. I have lived in almost 5 years. You have had a short visit.
Spending six weeks in a place is a vacation, not living there; spending six weeks on the road … is a road trip.
Living somewhere entails experiencing every season, managing utilities, paying taxes, being friends with the locals. Existing in a place involves speaking the language in order to communicate with the locals, not expecting everyone to gesticulate for the newbees, & not only knowing the local history but respecting it as well.
It seems to me that most Americans who move to Europe don't really know what they want. Perhaps that is true of most non-Europeans who arrive in Europe, looking for Nirvana.
Probably best that you return to USA or look to live in Mexico.
Would be better if real italians from US, Canada and Australia move back to Italy and reclaim their own culture instead of it being diluted and commercialized to interlopers.
why dont you go back to wherever you come from, Leave italy to those who appreciate the important things in life.
US people living or just moving through Europe are no doubt getting fallout from geopolitical stuff – like threatening to invade European-held territories, and reversal of support for Ukraine. I know this is a travelogue not a newschannel- but it's also now unfortunately part of your reality in Europe when dealing with the locals. No personal offence to anyone, but I can't say I blame them (the Europeans).
I have lived n Italy for 3 years. I am ready to go back to america.
Apologies 6 weeks in Italy does not even touch the surface. It's not even enough for a holiday. Please go back and spend 6 months instead. See more places .
"Italy doesn't replace Uncle Sam, it just joins him": Could you please clarify specifically? – Although it might seem self-explanatory.
The Europeans were bankrupted by the EU Project. The most heavily hit first were Italy, and France, but most all were impacted. At first, the weaker economies got money, like Ireland and Greece. The rest is history.
Lived in Rome, Naples and now Genoa (total 10 years); Preparing to move to Northern Europe, Overall not suitable for me; decaying infrastructure, aging demographics, No English, nightmare with utilities and dysfunctional apartments and difficult landlords who try to overcharge while not fixing things. Climate, food and scenic landscapes may go a long way but if you are from more modern countries, you will have disappointing times…
Is that your mom and dad with you? They have kind faces. I like the relationship you have with them.
What if health care is on top of the list. Will you find better health care outside the 7% tax region? Brad from Brad's World channel, his wife had a very big emergecy. They were lucky to had found medical attention quickly.
We still have lot's to learn as far as health care is concerned.
Thanks for sharing your experience. We really appreciate it.
cause italy and italians are the best
somehow Italy or Portugal or anywhere in Europe, doesn't look as good with Americans in the background or foreground..
As a true born Italian citizen, I love my country and know that it’s not perfect but the positive things surpass the negatives.
They were basically visiting the touristy spots. The beauty of Italy is the people and the culture . I have home in Sicily with a population of about 3000. We stay there every year and it because of the peoples and culture. That being I would never give living in America.
This video is very confusing as his delivery hems and haws at getting to the point.
Interesting information. If I could make a suggestion, I had a hard time understanding or hearing what you are saying. Maybe speak slower with more enunciation? Anyway thanks for the info
Im heading to Umbria region from Australia in June to volunteer on a farm for at least a month to get me grounded in Italian culture and look for a place to buy
YOU SPEAK WAY TOO FAST; after a bit, I changed sites…WHAT’S the point…? DRAMA…! 👎🏻😳
We are going back for our 4th visit only doing 10 weeks this time being my age at 81 my hubby being Italian we love it sadly to 9ld to go to live there .but would tomorrow .6 weeks is not long enough to really get the fee, of the 0lave we have travelled top to bottom .this trim coming in from Nice Nd Geneo to Milan again .travelling by train as ilove train travel.going to visit thr cousins near Venice to start then to Trieste to see more cousins still planning where else to go. Seeing we have been to most places trying to pick our favourite places we love .
hi, it would be great that you write the name of the town in France, sorry it is very difficult to understand the way you pronounce:)😀
Smaller towns Pompei 😅
So how are the social security and health benefits ?
Isnt Italy overrated compared to Bulgaria, Spain, Kroatia, Greece, Marocco, Turkia, Malta. It ssems to me Americans goes after the big headlines instead of going after more beneficial places.. as for instance South Africa.
It is fun, if you enjoy challenge and adventure.
Sorry but you need to talk a little slower. It’s a struggle to understand what you are saying and to catch the names of places etc.
This myth of the flat tax plan as some panacea, or the draw to Italy is a mirage, if you look into the particulars it becomes clear its not worth it, hence only around 1000 people participate in the scheme.
Guy reminds me of tiny Tim oh my
Uhhh you chose Naples as your first stop😂🎉😮 you were in for a seminar!!!!!
Love the pictures of the places I missed 2 years ago. Contemplating going back but not sure about southern Italy. I think I love Italian wine more than the Italians though. 😉
Thank you for making and sharing this video. You are the first person I have seen so far that explains the 7% tax for retirees based on city or locality population. And I have seen dozens of these expat videos. Cheers to you!
Idk how you didn’t know all of this. Did you not do your research? The dream is to do it in spite of the difficulties. To embrace the challenge and choose to become Italian… not stay an American. I understand following the numbers, but if that is your sole focus, you will not be happy anywhere.
Thanks for this interesting video. Are you related to Chris Hayes? You could be brothers!
Why oh why would you start in Napoli? Basta!
Italy 🇮🇹 is beautiful my Mother was from Calabria
Great video i truly enjoyed it
So ill stay in America where i was born….I have no problem in America….👍🏻 We have a GREAT PRESIDENT TRUMP ❤
I WILL WEAR WHAT I WANT
I WOULD NEVER Be DISRESPECTFUL Entering a CHURCH ⛪️
Instant follow. You are spot on!
Im 63yo Croatian New Zealander looking at my next chapter ….Ive always thought a town in Europe but as it comes closer I’m not so certain.
I didn’t realise how much I love the English language , efficiency , manners , excellent health care, stunning uncrowded outdoors.
I have been static for decades with raising a child , career, paying off a mortgage ….I’m craving history, culture, art …so I will go to Europe for 6 months and complete a couple of Caminos – Spain 🇪🇸 and Portugal 🇵🇹 and time in Croatia 🇭🇷 etc
Im realising my time is very limited – Ive had my nesting phase and now Im keen for a more nomadic period …6 months travelling overseas and 6 months travelling in a van in New Zealand 🇳🇿
You are so young. There are many phases to go ..good luck and I will enjoy following your journey
Too much effort for me.
I understood and followed you, despite your fast chat. It moves as a conversation, but not if intending being an informing media. I guess people have told you, as constructive criticism.
Thank you! Great video! I want to move to Portugal 🇵🇹
This is a truly great video! Thank you! Your story & descriptions, telling what a place is like, very good and easy to listen to. May I make one suggestion? Sometimes you rush through a word or phrase and we didn't understand what you said, sp please slow down and enunciate, ok?. And it would be great if you could tell us the proper pronunciation of a city or town you visit, so we can find it on the map! Just a thought….thanks again, looking forward to more of your videos!
Starting in naples is gutsy. Crime ridden and poverty
THANK YOU. is SARDINA PORTO🏖️🏝️🌅☀️ CERVO ANY BETTER ⁉️🕊️🙏🏻 6:56