I’ve lived in Italy for 20 years—and it changed me in ways I never expected. This isn’t a list of tourist tips. It’s what you really learn when you stay long enough to notice the details: the unspoken rules, the beauty obsession, the coffee curfews, and yes… the sidewalk parking.
In this video, I’m sharing the mindset shifts and daily habits that Italians just do differently—and how those lessons rewired the way I think, eat, and live. Some things I love. Some still drive me nuts. But that’s the beauty of it.
🛵 Want to experience Italy to the fullest? Download the Italy Insider E-Guide now! https://bit.ly/3Zom90m
Tenuta Cefalicchio, where I stayed: https://maps.app.goo.gl/AtN4bmML3YnVuK3C6
📧 Newsletter
Join my newsletter email list for free travel tips, hacks, and exclusive content. https://gregor-brown.kit.com/53b0eef2d7
👉Ways you can support me:
⭐Join my Patron Inner Circle
https://www.patreon.com/c/gregorbrown/membership
🙋🏻Join The Global Insiders for direct travel help and free guides.
https://www.patreon.com/c/gregorbrown/membership
📺Watch the next unreleased video by becoming a channel member
https://www.youtube.com/@GregorBrown/join
👍 Or simply just give a thumbs up, that’s free and much appreciated, too.
🙏And please subscribe for all the latest videos https://www.youtube.com/@GregorBrown?sub_confirmation=1
✈️ My TRAVEL INSURANCE recommendation 🩺 https://bit.ly/42FeDx0
🔗 Useful links
Agriturismo La Pimpinella di Semifonte: Agriturismo La Pimpinella di Semifonte
⚙ Gear I use for travel:
Plug adaptor: https://amzn.to/3HeyMAr
Power strip (plug into an adaptor): https://amzn.to/3JefEVP
Portable USB Charger (a must!): https://amzn.to/3kzrZcM
Italian phrase book: https://amzn.to/3wynZMv
Sleep eye mask: https://amzn.to/3IS7u4n
Ear plugs for sleeping: https://amzn.to/3IMOUuu
Toiletry Kit bag (I got the camo one): https://amzn.to/3Z2AM6B
Travel Bottles for Toiletries: https://amzn.to/3xT3WZN
…or get clear refillable ones: https://amzn.to/3ktjEHU
Samsonite hard shell luggage: https://amzn.to/404ZlRa
Rimowa Essential Cabin Luggage: https://amzn.to/3b1v94l
(If you buy using this links above, I receive a commission via the Amazon Affiliate Program.)

28 Comments
20 Years Living in Italy: What I Wish I Knew Sooner https://youtu.be/h4u4bLivLpQ?si=T24qXqr5vaPID1I4
Gregor, truley enjoyed this episode. Im from Stati Uniti. Im in process of moving to Castrovillari Calabria Italy. Love spening time in Tropea. Im solo and learning Italian is essential to your survival.
ty
If you still live in Italy, you say
I've lived in Italy fore 20 years.
I lived … means you no longer live there.
I bet Italians drink Capuchinos after 11 in secret too.
It sometimes happens that I haven't eaten at lunch, and so I order a cappuccino with a croissant. But it doesn't happen after 3:30 PM
The bartender doesn't look at me badly: but I'm Italian and therefore I'm allowed what is despised in a tourist 😆
Buongiorno, Gregor!! Loved this video and found your observations not only interesting but relevant. Years ago, after a divorce, I rented a room, which included "cena," for several years in the home of "familia italiana nativa" living in the US. I'm Italo-Americano, which is not considered a "thing" to native Italians, but I learned a great deal about the culture. Although I hesitate to call myself fluent, a year of studying Italian did help a great deal. I always dreamed of living in Europe, but life got in the way. I did make seven trips over the Atlantic in my time and I'm grateful for those travel opportunities.
Chuck in Northern New England (within striking distance of Canada)
I live near Miami, Florida. It must be the Latin influence because do many people here believe that traffic laws are merely a suggestion. Turn signals? I used them once. 😂😂😂 Love your stuff. My wife and daughter are pursuing dual citizenship. Although I'm second generation Italian American, my Grandfather became a naturalized US citizen and disqualified me for bloodline citizenship. Love your videos.
Is it true, that while walking down the street, strangers never make eye contact? I've watched some videos lately and notice they treat each other as if they owe them money, whereas, in the U S, even in New York, a smile usually gets you a return smile from a complete stranger.
What jobs are available for those who want to live there?
A perfect pizza is the greatest food ever.
A cat person here.
Watching this from a Sicilian balcony after watching your content for months
Gregor, we missed seeing you recently when we stayed next to the "My Bakery". We left and enjoyed "Fonte Bertusi" outside Pienza. How sweet it was!
Glorified Mexico 😂
I literally loved everything you said!👌🏼 And about the cappuccino rules, I heard they drink it early because milk is hard to digest. Whatever the truth is, I don't have any problem following this rule because italians know how to eat properly. I also believe I can fare uno strappo alla regola 😉
In Torino you can ask for a cappuccino whenever you want and you won’t be judged….so, come here, you are welcome😜🤗
I’m trying hard to live that life in Oklahoma. (Sips espresso in my cinquecento)
Gregor, I’d love to know what countries or areas outside Italy you’ve visited and would recommend in a multi country trip. Italian focus, but a few close places across borders or quick flights.
I love the connection to food and the slowness (maybe except for trains) and taking time to savor. We will be there for two weeks+ and hopefully we can enjoy some of that, for sure the food. Thanks Gregor!
I remember when I was in Italy looking at "new" buildings that were built in the 1,700s
Isn't it ironic?? I parked on an empty crosswalk spot for two minutes in TURN and got a ticket….so much for FREEDOM!!
Very happy to be living in the USA.
How can one be productive with a 3 hour lunch and one hour cappuccino??
Economics don’t make any sense
Someone else is subsidizing this lifestyle
Hi. I spent 7weeks studying Italian at a language school in southern Tuscany. It was a wonderful experience. I just went back for a refresher course and was surprised how many people remembered. While sitting in a park my first morning there, a car drove by , honked, and the driver shouted, “Ciao Douglas.” I was home!
Great video. I drink cappuccino into the night. Heading to Italy for the first time in September.
I really like your videos Gregor! They are so uplifting!
I'm so ready for Italy! Luongo piace mia! e anche mange bene! My high school Italian just might get me there!!
❤
20 years in Italy and you still don't know how to twirl your pasta? 🤨