This was the question I set out to answer. For this analysis, I focused in on Provinces of Italy, rather than cities. I chose this approach because cities and towns inside provinces tend to have similar characteristics, and choosing to live in a city, a suburb, or a small village is really a matter of lifestyle choice. There are 20 regions in Italy, and 107 provinces within those regions.
When evaluating the provinces, there are many different factors to consider, so I tried to zero in on as many objective metrics as possible. Since I was doing this evaluation for myself, I did tend to weight certain things that I felt were more important, and ignored other factors that mattered less to me. Here's the main factors that I considered, each one on a five point scale: Excellent, Great, Good, Okay, Poor. I pulled much of my data from the site https://expiter.com/ which I find to be a very comprensive site that has a ton of great information. Of course, many of the metrics found on this site are subjective, but it least it gave me a start.
Location
Proximity to Rome (drive time). Rome is the capital and has by far the most international flights. I gave preference to locations that afforded a short drive to Rome. Note: This does not take into account the train systems in Italy. The highest speed trains to and from Rome are the cities of Milan, Florence, and Naples, and by extension to Bologna and Torino. Also note that there are planned high speed trains through Campania and into Calabria.
Political Majority. I gave a slight edge to provinces that were right leaning. I did this for two reasons. First, the whole of Italy is currently more inclined towards the right, so finding provinces that are right leaning will be more aligned with the direction of the country. Second, I believe that right leaning areas are generally better goverened, less taxes, less bueracracy. All things being equal, I'd rather live somewhere that leans right than leans left.
Healthcare
Safety
Air Quality
Cost
Region. I gave a slight edge to Provinces in the South, because Italy is trying hard to lure people to the Southern regions and offers a 7% Flat Tax if you move to the south and to a city with less than 20,000 people. This may not matter to you, but it's a pretty big possible upside if you qualify for the FEIE (if you don't qualify, there's really no incentive, as you'll have to make up those taxes to the US government
Cost of Living. This was pulled from expiter.com, but could have also been pulled from other sites, like Numbeo.com.
Nomad Cost. "Nomad Cost" tends to follow "Cost of Living", so this might be counting cost twice, but there sometimes is a difference between general cost of living and the costs associated with an expat.
Natural Beauty
Beach Score. I counted this one twice because, well, I love the beach
Hiking Score
Culture
Nomad Score
High Speed Internet
Nomad-friendly
English speakers
Overall Happiness
I then calculated each of these scores for each of the 107 provinces, and sorted from highest to lowest score. Here are the top 20 areas:
The Top Provinces of Italy, ranked
Note: Yellow pin indicates international airport
Excellent beaches, very low expenses, nomad friendly, fast internet. Far from Rome, but only 2.5 hours from airport in Catania.
Representative Villa: 2800 sqft, 3 beds, sea views, $400,000 USD
Excellent beaches, reasonable prices, 2 hour 20 minute drive to Rome, good English speaking, excellent culture, fast internet.
Representative Villa: 7400 sqft, 1/2 acre, sea views and 15 minute walk to the beach, $600,000 USD
Very similar to Pescara, except better safety and not quite as good culture. Still 2.5 hours to Rome.
Representative Villa: 2300 sqft, nearly 2 acres, short drive to the sea, $500,000 USD
Further up the Adriatic coast, affordable living with great healthcare and safety, excellent air quality and culture, more temperate weather, 3 1/2 hours from Rome by car.
Representative Villa: 4800 sqft, 1 acre, tennis court, sea views, $865,000 USD
Island living known for long and healthy lives, Cagliari is affordable but offers excellent healthcare, great safety, incredible beaches, incredible culture, and known to be very friendly to expats. Fly in to Rome from the airport in town for $170
Representative Villa: 4400 sqft, basketball court, swimming pool, 6 bedrooms, $650,000 USD
There is a promised high speed train all the way to Reggio Calabria which will make the trek to Rome more manageable, but this area boasts some fantastic beaches, some of the cheapest costs, and being very friendly to expats
Representative Villa: 4 fully furnished and self heating apartments, 15,000 sqft, across the street from the beach, $706,000 USD
Located due east of Florence, Forli-Cesana in the Emilia-Romagna Region is a four hour drive to Rome and has excellent air quality and culture, great beaches, and an average cost of living.
Representative Villa: Large villa with swimming pool on half an acre, $490,000 USD
Very nomad-friendly great internet, great beaches, great hiking, and low cost of living. International airport right in town.
Representative Villa: 3400 sqft, gated entry, sea views, $380,000 USD
Also with an international airport, the province of Palermo has rich culture, incredible beaches, great air quality, very nomad friendly, and very inexpensive. One hour flight to Rome is $100 each way.
Representative Villa: 4000 sqft, gated property overlooking Cefalu, swimming pool, $650,000 USD
Our highest scoring Northern Italian province, Genoa has great healthcare and culture, and excellent marks in happiness, internet, and beaches. The prices are a little steeper, but the weather is also much more temperate with August highs in the low 80s and January lows still above freezing.
Representative Villa: 3200 sqft, 3/4 acre, privacy and serenity, $700,000 USD
On the Adriatic, Bari is very nomad friendly with excellent internet and beaches. The air quality and the culture could be better, but the price is certainly right.
Representative Villa: Start your Wedding reception business at this 4300 sqft, 3 acre property with 6 bedrooms and 6 bathrooms. $750,000 USD
Cracking the top 15 is the fourth province of Sicily. Excellent beaches, very inexpensive, nomad friendly and very safe.
Representative Villa: Bring everyone to this 7000 sqft villa with 5 separate apartments and two courtyards. $590,000 USD
An hours drive to Rome, Terni offers excellent happiness, plenty of English speakers, and an affordable price. There's no beaches, but an easy transition for the expat.
Representative Villa: 3600 sqft and half an acre, small swimming pool and sauna. $440,000 USD
Northeast Italy offers good beaches and good hiking in Ferrara. This province offers great healthcare and excellent culture for the average Italian pricetag. Plenty of english speakers and a generally happy environment.
Representative Villa: 6000 sqft house and barn in the country surrounded by 1.25 acres, $540,000 USD
Located in the NorthEast corner of Italy bordering Slovenia, Trieste offers a great expat experience with more fluent English, friendly to foreigners, great internet, and decent beaches, albeit far from Rome and a bit more pricey.
Representative Villa: 4800 sqft fairy-tale type house and grounds with a peekaboo view of the sea. $740,000 USD
The province of the Eternal City, Rome offers fluent English, the best cultural treasures in the entire world, and a friendly environment to expats. You are also a short train to catch a plane anywhere. More expensive but deals are available in the outskirts.
Representative Villa: 3800 sqft, a short drive to the sea, panoramic views, and positioned on an acre of land. $400,000 USD
Just due west of Milan is the province of Vercelli, which does not have a beach but does boast excellent hiking. Also you will find great healthcare, many English speakers, and happy vibe, and close proximity to the amazing culture and the airport of Milan. Prices are average for Italy.
Representative Villa: 6700 sqft, 1 1/4 acres 1930's villa in the middle of wine country. Includes a caretakers house, a small pond, and a tiny cottage. $650,000 USD
On the island where people routinely live to 100, Nuoro is extremely inexpensive yet boasts excellent healthcare, fabulous culture, great hiking, and first class beaches.
Representative Villa: A house that would fit in Wailea, 3200 sqft and 4 bedrooms with a view of the beach. $580,000 USD
A two hour drive to Rome, Teramo offers good culture and excellent beaches at a fairly affordable price.
Representative Villa: 7400 sqft and a ten minute walk to an incredible dog beach, this villa has four bedrooms over three levels and produces income as a B&B. $600,000 USD
In the south off the Ionian Sea is Matera, which is very inexpensive but still boasts great safety, culture, and beaches. Healthcare and air quality may be a problem.
Representative Villa: 4300 sqft and a few km from the beach, this property has an ornamental garden, a tennis court, and a bowling green. $310,000 USD
While receiving lower marks in air quality and culture, Cosenza is an incredibly inexpensive place to find great hiking, excellent beaches, and plenty of sun on the mainland. It is also considered to be very nomad friendly.
Representative Villa: 3 separate apartments spread over 3300 sqft, an acre of land with two outdoor showers and 90 olive trees, and views of the Ionian Sea. $470,000 USD
The province of Naples has it's own international airport and is a very short high speed train from Rome. Great beaches, nomad friendly, and somewhat reasonable prices outside of the city.
Representative Villa: 4 separate apartments (2000, 800, 800, 600 sqft) with courtyard. $511,000 USD
South of Naples and a reasonable distance from Rome is Salerno, known for great beaches, English speaking, and nomad friendly. Not known for great air quality or healthcare.
Representative Villa: 3700 sqft, fantastic views of the sea, an olive grove, and in a quiet residential area. $550,000 USD
Great healthcare, air quality, and hiking can be found in Northwest Italy. Also known for being very friendly to nomads and fluent in English. Two hour drive to Milan
Representative Villa: 6400 sqft, 1.25 acres, suitable for three families or as a farmhouse B&B. $710,000 USD
On the west side of Tuscany is Grosetto, known for excellent healthcare, great beaches, and happy people. The prices are a bit higher and the air quality may be suspect.
Representative Villa: Originally the residence for the Counts of Bologna, this villa offers 6 bedrooms on a quarter of an acre. $320,000 USD
Amanda Knox story withstanding, Perugia is centrally located with happy people, great internet, and fantastic hiking. Just over a two hour drive to Rome. Air quality not the best.
Representative Villa: 4600 sqft and 11 acres (including a productive olive grove and woods), 5 bedrooms, and close to the city. $740,000 USD
Evaluating Tax Advantages
Italy and the United States have a tax treaty, which means that you cannot be double taxed on the same money. As a US citizen, you are always required to submit a tax return each year in the United States, but the implications of what you pay in taxes can vary based on where you are spending your time and what tax breaks you may qualify for in Italy.
Both Italy and the United States have a progressive tax, which means you pay more in taxes as you earn more income. Italy's tax rates are generally more progressive and steeper. For example, a couple that earns $200,000 USD would pay $44,800 in the United States in federal taxes, and pay $83,283 in Italy. This is because the tax rates increase more quickly and are much higher in Italy than the United States, as you can see below:
United States Income Tax Brackets, 2024
10% on income up to $22,000
12% on income over $22,000 up to $89,450
22% on income over $89,450 up to $190,750
24% on income over $190,750 up to $364,200
32% on income over $364,200 up to $462,500
35% on income over $462,500 up to $693,750
37% on income over $693,750
Italy Income Tax Brackets, 2024
23% on income up to €15,000
25% on income over €15,000 up to €28,000
35% on income over €28,000 up to €50,000
43% on income over €50,000
However, Italy does offer a few different incentives (called "tax regimes") to lure people to move to Italy, especially to smaller towns in the south of Italy. One of the primary regimes is called the 7% Flat Tax. This is for people who move to smaller towns (<20,000 people) in southern regions (and <2000 people in the central regions) from another country. The 7% flat tax is good for a ten year period.
Scenario 1: Take the same couple who makes $200,000 and lives 200 days in Italy (let's say a northern region) and the remainder of the time in the United States. This couple now has a tax obligation in both countries, but will not be doubled taxed for the same money. So, they first pay a 7% flat tax for the $200,000 in Italy, and owe the Italian government. They would first pay taxes to Italy and be responsible for the $83,283 to the Italian government in taxes, as calculated above. They would then claim a Foreign Tax Credit in the United States of $83,283, and begin calculating their tax obligation to the United States, which was calculated above at $44,800. Because they already have a foreign tax credit that is bigger than this amount, they would pay no money to the United States. Total tax liability: $83,283 (equivalent to Italian taxes).
Scenario 2: Now, let's assume this couple moves to a smaller southern town and qualifies for the 7% flat tax for the 10 years. They would pay $14,000 to the Italian government (7% of $200,000), and then carry a $14,000 Foreign Tax Credit to the United States. In the United States, they would have a tax obligation of $44,800 (again, calculated above), and removing the $14,000, they would pay the US government $30,800. Total tax liability: $44,800 (equivalent to US taxes).
Scenario 3: Now, let's assume that this couple absolutely loves the food, the culture, and the people of Italy and decide to stay in Italy pretty much full time. Because they are living full time in Italy, they qualify for the Foreign Earned Income Exclusion (FEIE) of the United States. The FEIE provides a tax exclusion of $120,000 per individual on earned income (not retirement or investments, but actual earnings). The couple would still pay the $14,000 to Italy, but the remainder $186,000 is less than $240,000 ($120,000 x 2), so the couple would not have to pay taxes in the United States. Total tax liability: $14,000.
Income Potential and other Considerations. Of course, the potential for earning an American sized salary in Italy (especially in a smaller southern town) is not always practical. However, the amount of money that you would need to earn to afford the same quality lifestyle may not be as much in Italy as it is in the United States. Here's a basic cost of living breakdown between Bellevue, Washington (where I happen to be from) and Palermo, Sicily (numbers from Numbeo):
Cost of Living in Bellevue, WA is 46.6% higher than in Palermo (without rent)
Cost of Living Including Rent in Bellevue, WA is 112.1% higher than in Palermo
Rent Prices in Bellevue, WA are 393.3% higher than in Palermo
Restaurant Prices in Bellevue, WA are 74.5% higher than in Palermo
Groceries Prices in Bellevue, WA are 43.5% higher than in Palermo
Local Purchasing Power in Bellevue, WA is 208.1% higher than in Palermo
The same couple that earns $200,000 in Bellevue, Washington would only need approximately $94,287 in Palermo to maintain the same quality of life. These calculations are not including taxes and tax savings that you would be afforded should you also qualify for the 7% flat tax (which again is good for only ten years). Here's the equivalent amount of money you would need in some of the provinces above (where the data is available) to maintain the same quality of life that $200,000 would provide you in Bellevue, Washington:
Messina: $85,459
Pescara: $101,112
Cagliari: $110,125
Reggio Calabria: $73,842
Forli-Cesena: $108,789
Catania: $86,371
Palermo: $94,287
Genoa: $113,736
Bari: $99,331
Turin: $83,767
Trieste: $106,044
Rome: $116,677
Vercelli: $91,820
Teramo: $88,363
Matera: $86,896
Cosenza: $82,507
Naples: $106,759
Salerno: $96,809
Turin: $107,400
Perugia: $91,770
Which place checks the most boxes?
It is largely up to personal preference which location you might consider above others, and the scoring above represents an view based on a variety of factors. Another way to look at it is to identify which factors mean the most to you, and then find the location or locations that check each of these boxes.
For me, I like to look at factors which can be easily mitigated and which cannot. For example, proximity to Rome is a factor that cannot be easily mitigated. If you decided you wanted to live within 3 hours from Rome, then to mitigate a location farther away would require charter planes. However, a factor that can be somewhat easier to mitigate is how many English speakers that live in an area. To mitigate this factor (with somewhat relative ease), you simply need to immerse yourself in the culture and learn Italian.
So, here are the factors that I believe are important and also difficult to mitigate:
Air Quality
Proximity to Rome
Beaches
Culture
Safety
I consider these 5 factors to be the most important factors when choosing a location. So, with this in mind, I went back and looked at the provinces that have a rating of "great" or "excellent" in these five areas.
Only one province (Ancona) scores Great or Excellent marks in all five areas. Ancona was ranked as "Excellent" in Air Quality, Culture, Internet, and Happiness. It received the ranking "Great" for Safety and Beaches. It is roughly a 3 1/2 hour drive from Rome, and is considered "Affordable" in terms of cost. It has a July high of 81 and a January low of 36. It is never freezing and never hot. It does get muggy in July and August, but rarely oppressive.
Chieti lacks the Culture (ranked "good"), but makes up for that with "Excellent" air quality and beaches. It has less chance of humidity than Ancona, and is just over a two hour drive to Rome.
The one location in Tuscany is Sienna, which doesn't have the beaches, but makes up for it with "Excellent" health care, happiness, and culture, and "Great" air quality. Sienna can get hot, but will not get muggy.