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We are looking to move to either Portugal or Italy in the next few years. Being just a few hours flight away from basically any major European area is pretty sweet and that's what we want to take advantage of.

I looked at Panama as an option. I would love it mainly for the year-round kitesurfing (and hot weather to go with it). It's also a quick flight back to Canada if we need to come home. My girlfriend isn't keen on the vaccines you would need for Panama (I already had them all from going there before and other places), and potentially taking the antimalarial. Night terrors are a real side effect that my friends have had (but I did not). but honestly you don't need to take the antimalarial daily. Just use a super dose if you actually get malaria.

Also cost of living is way cheaper.

But we both prefer Europe for long-term living.... so that's probably what we'll do.

For what it’s worth, I lived in Florence for a while. My wife and I are also headed permanently to Europe (or New Zealand if we can swing it) in the next few years.

Definitely check out some less famous areas. I go to Bologna once a year for other reasons and that’s definitely the Italian city I would choose at this point. But it’s all just personal lifestyle preferences. I value walkability more than most. You never know until you actually try it. And not just as a tourist.
 
We are looking to move to either Portugal or Italy in the next few years. Being just a few hours flight away from basically any major European area is pretty sweet and that's what we want to take advantage of.

I looked at Panama as an option. I would love it mainly for the year-round kitesurfing (and hot weather to go with it). It's also a quick flight back to Canada if we need to come home. My girlfriend isn't keen on the vaccines you would need for Panama (I already had them all from going there before and other places), and potentially taking the antimalarial. Night terrors are a real side effect that my friends have had (but I did not). but honestly you don't need to take the antimalarial daily. Just use a super dose if you actually get malaria.

Also cost of living is way cheaper.

But we both prefer Europe for long-term living.... so that's probably what we'll do.

Portugal vs Italy is interesting. Ofc a lot more city choices in Italy... but I prefer Portugal tbh.
More international, far higher level of English, way more relaxed people.

If you like kite-surfing then surely it is Portugal! Some of the best spots in Europe there and in Spain which ofc is a short drive away.

Was looking at Panama actually for a holiday this year aha. Panama, Costa Rica, St. Lucia, Indonesia, Philippines and Tanzania kind of the finalists... but will have to go in August-September so weather wise etc Tanzania has an advantage.
 
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For what it’s worth, I lived in Florence for a while. My wife and I are also headed permanently to Europe (or New Zealand if we can swing it) in the next few years.

Definitely check out some less famous areas. I go to Bologna once a year for other reasons and that’s definitely the Italian city I would choose at this point. But it’s all just personal lifestyle preferences. I value walkability more than most. You never know until you actually try it. And not just as a tourist.

Thanks for the recommendation on Bologna.

Were you also working when you lived there? And was it for an Italian employer or remote working for a US employer?

Have you visited the east coast of Italy, like the Apulia region? Other than Italy, we're also open to Montenegro or Croatia (even Serbia) across the Adriatic. But I have heard great things about the south east coast of Italy.
 
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Thanks for the recommendation on Bologna.

Were you also working when you lived there? And was it for an Italian employer or remote working for a US employer?

Have you visited the east coast of Italy, like the Apulia region? Other than Italy, we're also open to Montenegro or Croatia (even Serbia) across the Adriatic. But I have heard great things about the south east coast of Italy.

Montenegro and Croatia are beautiful but I dont think I could live there permanently. Slovenia is for me the best of the Balkan states for livability, but also kind of the most boring too in some ways. I love Macedonia, crazy beautiful, but yeh... would not live there. I have some strange affinity for Belgrade... but not sure a place to live long-term.
 
If you can when in Naples... go to Pompeii... incredible to see. Only maybe an hour on the train.

Naples is a very interesting city in itself though. Bit wild though in parts. Saw an attempted murder within 5 minutes of arriving for the first time.

Florence is also very beautiful but you cant move for tourists.

I love Malta. Awesome place to be.
We already booked Pompeii! I am really looking forward to to it.
Hoping to try the pizza in Naples, and avoid the murderers lol
I think we are going tee Pisa when we stop in Florence and as history buff I am looking forward to Malta too. I hear Valletta and Mdina are beautiful.
This is a great trip.
 
Portugal vs Italy is interesting. Ofc a lot more city choices in Italy... but I prefer Portugal tbh.
More international, far higher level of English, way more relaxed people.

If you like kite-surfing then surely it is Portugal! Some of the best spots in Europe there and in Spain which ofc is a short drive away.

Was looking at Panama actually for a holiday this year aha. Panama, Costa Rica, St. Lucia, Indonesia, Philippines and Tanzania kind of the finalists... but will have to go in August-September so weather wise etc Tanzania has an advantage.

Yes there's something about the Italian culture that just keeps pulling me back - but I also really liked Portugal when I went. Visited Lisbon, Oporto, and parts of the west coast, but did not make it down to the Algavre.

Do you live in Portugal now?

For kitesurfing, I imagine the Atlantic gets a bit too cold in the winter months? I can do it in Canada until about October or maybe even November, but then even with a wetsuit it just gets too annoying to deal with setting up when surface temperature is hovering around 7-8 C. And the winds are less cooperative.

I have heard about Tarife, Spain as kind of the mecca for kitesurfing. And there's a short ferry ride to Morocco, which would be really fun.
 
Yes there's something about the Italian culture that just keeps pulling me back - but I also really liked Portugal when I went. Visited Lisbon, Oporto, and parts of the west coast, but did not make it down to the Algavre.

Do you live in Portugal now?

For kitesurfing, I imagine the Atlantic gets a bit too cold in the winter months? I can do it in Canada until about October or maybe even November, but then even with a wetsuit it just gets too annoying to deal with setting up when surface temperature is hovering around 7-8 C. And the winds are less cooperative.

I have heard about Tarife, Spain as kind of the mecca for kitesurfing. And there's a short ferry ride to Morocco, which would be really fun.

Yeh, right in the centre of Lisbon! The Algarve is very cool too. Different as not technically full on Atlantic Coast.

The sea temperature in Portugal does not drop that low... it doesnt drop below around 15c all year! People are often out surfing on Christmas Day.

For example this is the main beach just south of Lisbon: Costa da Caparica Beach Water Temperature / May 2025/ Portugal | World Beach Guide

From Lisbon down the country has basically Central California winters... not quite LA or Santa Barbara but warmer than places like Monterray... maybe similar to San Luis Obispo looking at the map?

Even in Winter almost no days drop below 10c air temp... average day from December-February is about 12-14c air temp.

I love Morocco. Helps my girlfriends family are from there... but just a very special country.
 
We already booked Pompeii! I am really looking forward to to it.
Hoping to try the pizza in Naples, and avoid the murderers lol
I think we are going tee Pisa when we stop in Florence and as history buff I am looking forward to Malta too. I hear Valletta and Mdina are beautiful.
This is a great trip.

Yeh, Malta has so many amazing archeological ruins too... such an interesting country with the mix of Arabs and Italians over time. Language is wild.
 
Thanks for the recommendation on Bologna.

Were you also working when you lived there? And was it for an Italian employer or remote working for a US employer?

Have you visited the east coast of Italy, like the Apulia region? Other than Italy, we're also open to Montenegro or Croatia (even Serbia) across the Adriatic. But I have heard great things about the south east coast of Italy.

At the time, I was a US citizen working remotely for a firm based in NYC.

Croatia was beautiful but just not my kind of lifestyle. That doesn’t mean it’s bad or anything of course. It just means any info I give is going to be skewed. That’s not fair to you. Montenegro I’ve never seen.

Southern Italy is something I would STRONGLY suggest you attempt to immerse yourselves in before uprooting your lives. I have never been to Apulia to the best of my recollection, but I have family in Calabria and spent some time in places like Scilla and Amantea. Maybe it varies from east to west coast, but I found it to be a completely different animal compared to the north. There was some culture shock for me personally. Nothing off-putting. But definitely different in ways I don’t think would fit my personality well permanently.
 
We are looking to move to either Portugal or Italy in the next few years. Being just a few hours flight away from basically any major European area is pretty sweet and that's what we want to take advantage of.

I looked at Panama as an option. I would love it mainly for the year-round kitesurfing (and hot weather to go with it). It's also a quick flight back to Canada if we need to come home. My girlfriend isn't keen on the vaccines you would need for Panama (I already had them all from going there before and other places), and potentially taking the antimalarial. Night terrors are a real side effect that my friends have had (but I did not). but honestly you don't need to take the antimalarial daily. Just use a super dose if you actually get malaria.

Also cost of living is way cheaper.

But we both prefer Europe for long-term living.... so that's probably what we'll do.
I lived in Italy for 2 years and did a reno project that lasted over 10 years and involved a court case. Portugal is one of the most open countries for expats (although US remote workers driving up housing prices and rents have pissed some people off). Italy is one of the best countries to visit, but they do not like foreigners. It is voted as one, if not the worst countries for expats to live.

Edit: 48th of 53 countries: Expat Insider 2024: Of Visa & Working Woes in Italy

Portugal:
 
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Portugal was a dope vacation. Crazy nice people happy to speak English, beautiful, amazing weather, and cheap as hell.
My wife and I are probably going to do Portugal in Feb, we like to escape the gloomy, cold weather for some nice sunshine. We went to Switzerland (partial work), and Florence last year and we'll do Scotland and Switzerland (partial work) this year.
 
This thread has improved 100% with the travel talk.

After doing a year long world trip (25 countries, 366 days) that ended last year, I am off again for most of June. Portugal, Sweden, Finland (most of my time will be spent there), a quick stop in the Netherlands and then a couple nights in Venice before back to Canada.

I’m moving to Malaysia in 2027 to begin a life abroad. Travel is the life for me.
 
This thread has improved 100% with the travel talk.

After doing a year long world trip (25 countries, 366 days) that ended last year, I am off again for most of June. Portugal, Sweden, Finland (most of my time will be spent there), a quick stop in the Netherlands and then a couple nights in Venice before back to Canada.

I’m moving to Malaysia in 2027 to begin a life abroad. Travel is the life for me.

If you are in Lisbon sent me a PM and will buy you a drink if I am around.
 
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Portugal was a dope vacation. Crazy nice people happy to speak English, beautiful, amazing weather, and cheap as hell.

Yeh, the level of English is by far the highest in Southern Europe... tbh in Lisbon and Porto the level of English amongst basically everyone under 50 years old is what you would expect in Scandinavia really.

The main reason aparently? They sub and dont dub TV aha.
 

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