Where would you spend 3 months in Italy?

Be aware that unless you are a EU citizen, you will be limited to a 90 day stay (not 3 months). There are stiff penalties for exceeding that limit even by a day.

Unless you have a car, I suggest a major railway hub. That would be: Rome, or Florence, or Bologna, or Milan, or Naples (depending on your preferred areas for day trips).

All of them will be hot in summer.. The only places that are not hot are somewhere up in the mountains (as high as possible), but unfortunately all major cities in Italy are rather low in altitude.

PS: Grazie is spelled without a “t”.

We just got back from Italy and LOVED Bologna and Ortesei!! Bologna was lovely and is close enough for you to explore other cities ! :) Great food markets , LOVED the porticos, felt comfortable and safe! :) We stayed at an amazing AirBnb and host was lovely!
We took an awesome Gelato making class there too!

Hello All-Time-Lolo, and welcome to the forum!

Full disclosure I am planning on spending a month in Lucca so my research has been concentrated there and I don't have kids going with me so that hasn't been specifically in my research.

I think Lucca (inside the walls) would make an excellent choice for this assuming the pricing works for you as "affordable". The city is very safe, mostly pedestrian, and there a multiple play areas in and around the walls and kids are often allowed to simply go on their own or play collectively with a gathered group of parents and nonnas watching out for them. It is connected by train to Pisa and Viareggio for going west and up and down the coast as well as Florence for fast trains to other parts of Italy.
I have learned a bunch from the podcast: LIFE IN LUCCA WITH ANDREA about daily life, expats and city itself.

If you are open to rural areas you might look into Bagni di Lucca which is a collection of a bunch of small towns collected in the hills above Lucca that considered together collectively as a single community. You're obviously getting out of the well connected to rail since you're outside even Lucca which is outside Florence but while Lucca is surprisingly close to nature Bagni di Lucca is in nature.

You might also look into Pistoia which is nearby and while more modern than Lucca is often listed as a bigger sister kind of city and is better connected with Florence by train. Several people who ended up in Lucca mention Pistoia as the other place they were considering.

Siena would make an interesting choice. I stayed there for several day last year and even in October I was surprised by the amount of tourists. It is a beautiful and interesting city and a guy from Brooklyn who we randomly chatted with while doing laundry sang the praises of Siena as a calm and safe place to live after moving there in 20-teens after visiting once. It is about 5x bigger than Lucca (inside the walls) but still smaller than Pistoia population-wise at least.

Arezzo is smaller, less famous and touristy town that you might look into. Its is an interesting mix of modern city in the flat and then slowly morphing into the ancient town as you run up the hill. I can't vouch for how it is for kids but it is rated as "boring" by university students versus Siena so that might give it a thumbs up in terms of being a quieter place to live.

If you've entertained someplace as large as Bologna you might look into Verona. It is an arty town with medieval buildings featuring faded frescos and that "beautiful decay" that the Veneto does so well tucked in the bend of the river. The old town area is largely pedestrian and has a very cafe culture where the Opera season takes place in the old Roman Arena. The old town core seems much smaller than the city population would suggest. Anything in the San Zeno, Città Antica or Veronetta neighborhoods would put you within the city core. There is also the Borgo Trento which is a peninsula filled with just stacks of modern housing but much of it is still tree lined and city core adjacent.

Coastal towns are often difficult rentals depending on the time of year because the owners want to rent them out during the summer for 4x the price for those months. Coastal towns also often have more of an open and closed season than inland places. San Terenzo is smaller, sleepier town south of La Spezia connected by ocean boardwalk to the resortier Lerici which has a marina. Any Italian coastal area will be filled with tourists in the summer but at least tourists will mostly be Italian.

Since it sounds like you've lived a bunch of cities I'll leave out the usual visa warnings but I will mention that rental contracts in Italy have their own oddities sometimes. I would work with a real estate agent or at least have on call to confirm all the details and make sure you're registered with the local police and other Italian oddities.

Sounds great,
=Tod

We spent eight weeks in Venice.

Twice

Loved it.

Milan, the lakes on the Swiss border; Verona, Venice, Ravenna, Bologna, Cinque Terre, Sienna, Pisa, Lucca, Florence, Perugia, Assisi, Spello, Spoleto, Orvieto, Rome, Sorrento, Capri, Naples, Pompeii, Amalfi Coast, Salerno. If you have time a week in Sicily.

Lucca is a great choice with small children, mainly because it is flat (in addition to it being lovely). We've been twice when our kids were smaller and loved riding bikes around the walls. I definitely would not choose Venice as having two young children there would give me constant anxiety.

We loved Verona and thought it was a place we could live in. it has good rail connections and is near to Lake Garda which we also visited.

Of your four choices, I would say Bologna offers the best connections to other places—-it is a major train hub for trains in all directions. Siena is lovely, but it is a case of “you can’t get there from here”——you pretty much have to start a journey to anywhere else by heading to Florence and connecting there. You will pass San Gimignano and Certaldo on the way, but if you go the other direction from Siena, the regional train wanders off to villages you never heard of.

Lucca and Pisa would also require a return to Florence to visit elsewhere, unless you wish to go up or down the coast.

What I like to do when studying places to visit or stay in Italy is to start with the Satellite View on Google or Apple Maps, and look closely at the town for city for green spaces—-parks, gardens, street trees, or trees in piazzas. These green spaces make anyplace much more comfortable in summer. Look closely at Lucca and you will see almost no green inside the city walls, apart from the far eastern end, and the trees planted on the wall itself. We spent 2 June days in Lucca and found it unbearably hot because of that—-all that unshaded concrete soaking up the sun and radiating the heat back.

Bologna also has little green space inside the city walls, but it does have the famous porticos——breezy covered walkways or colonnades lining the streets of the city center and elsewhere. These provide shade and also a safe and pleasantly wide sidewalk, separated from vehicle traffic. We find walking around Bologna a pleasure thanks to these.

Two places I will add to your list for consideration: Verona and Ferrara, both quite near Bologna. Verona has already been mentioned, and I agree with that recommendation. The city itself is quite charming, and just outside the walls, where most people live, you will see lots of healthy green space. My husband’s Italian tutor, who hails from Milan, says we should consider Verona for our own next long-stay in Italy (last time we stayed in Venice and loved it, but that was not in summer).

Ferrara has not been mentioned yet, but I think it might be perfect for your needs and wishes. It has direct (no changes) connections to Padova and Venice to the north, and Bologna and Rimini (with Roman sites and a castle as well as a huge beach) to the south. There is also a line to Ravenna, but it appears to not be in service right now.

The town itself is lovely, with a large pedestrian-only area around the main piazza, and a fair amount of green space inside the city walls, with more jut outside. We walked the walls and saw some very nice neighborhoods inside the walls. We found the people there to be among the friendliest we have met in italy, perhaps because the city is not overrun with tourists. My husband was able to use his Italian there good effect—-people continued to converse with him in Italian even if they spoke English.

I think I may have just talked myself into proposing Ferrara for our own next long stay. . . .

Be aware that unless you are a EU citizen, you will be limited to a 90 day stay (not 3 months).

That's true for routine Schengen entry, certainly, but cannot one visit an Italian embassy in the US and request a visa for a somewhat longer stay in a case such as this?

Bologna isn't too bad, you'll have to deal with the heat as you're looking at the heart of the hot weather months. As already mentioned, it's a transportation hub not only for train-travel but, also by vehicle. Centrally located in Emilia-Romana, you're not far from Florence, Milan or, Venice, not to mention the Dolomites aren't too far away, as are other parts of Tuscany.

The coast is nearby, either historical Ravenna, beach-side resort town of Rimini or, micro-country San Marino. Your kids are quite young, beaches are easy entertainment for them and weekend rentals are common.

Milan would be a second choice, you're at the base of the Dolomites and has all the big city amenities. Switzerland and France aren't too far away as are the many coastal communities of the Cote D'Azure or, travel on the highway under Mount Blanc to Annecy (Venice of France), Grenoble, Chamonix and Geneva.

Milan is close to Lakes Como and Maggiore, as well as Switzerland and France. But not to the Dolomites. And if they want a place to speak Italian with the locals, they will do better elsewhere. I would not suggest Milan for OP's home in Italy for 3 months based on proximity to the Dolomites. 4+ hours away by train is not a reasonable day trip, especially with small children.

@jphbucks
I mentioned the 90 day Schengen restriction because there are a lot of people out there who are not aware of its existence.
Yes, there are circumstances where one can ask for a long term visa, but those are limited to specific situations (e.g. work, study, elective residency, adoption, family reunion, diplomatic visas, NATO military personnel and family members, medical care, missionary and volunteer work).

If for tourism the limit is 90 days. There is not a tourist visa for periods longer than 90 days over a 180 day rolling period. To stay longer one must apply for a long term visa based on the reasons described above in parentheses and all of those long term visas require a bureaucratic and approval procedure to obtain.

Two lovely smaller towns that will be less crowded with tourists in the summer, but have easy train access are Vicenza and Bassano del Grappo. There is also Parma which has a beautiful, large park always filled with families.

Roberto, I think it's always a good idea to mention the 90 day Schengen limit in posts like this one. I have never, and don't envision ever, traveling for 3 months, but if it weren't for this forum, I would not know the limit existed.

Roberto, I think it's always a good idea to mention the 90 day Schengen limit in posts like this one. I have never, and don't envision ever, traveling for 3 months, but if it weren't for this forum, I would not know the limit existed.

We're actually spending 89 days in the Schengen Zone this year. The calculator available online is a godsend.

Probably for your request you have to chose. Good train connections are in cities, towns and villages located in the flatland and obviously very warm in full Summer. Smaller places, colder at least during the night, are located far from train lines or on secondary railway not very well connected.
Bologna, as suggested, could be a nice place to stay and probably in full Summer the rate for rooms won't be too high (in ine of the most expensive Italian city where to rent a flat). On the coast even the Rimini - Riccione area could be interesting: crowded by tourists but not too expensive. And a lot of fun for babies.
In general if you stay in a city where there aren't so many tourists (Venice, Florence and so on) people is kind with tourists and you will have no problem to become part of the group. And in any town and city during Summer are arranged several activities and local fairs suitable for families.

Padua is where we would stay for 3 months if Rome, Florence, and Venice were off the table — we spent 9 nights there and wanted to stay longer. It seemed very livable and friendly, and the food market is great. Many small piazze besides the two big ones.

Scrovegni Chapel, with Giotto’s frescoes

narrow medieval porticos like Bologna’s

Piazza delle Erbe and Piazza della Frutta for fruit and vegetable markets and general enjoyment (gelato shops, etc.)

13th century Palazzo della Ragione with indoor food market on ground level and huge frescoes in the upstairs great hall

Torre dell’ Orologio with its medieval clock

2nd oldest university (1222) with Mannerist loggias, Galileo's chair, & 16th century anatomical theater with skin-free human sculptures

Romanesque Gothic St. Anthony’s Basilica, with domes like San Marco's in Venice, 14th century frescoes, works by Donatello

16th century botanical garden

easy train connections to Verona, Venice, etc.

except for art lovers visiting the Scrovegni chapel and pilgrims visiting the basilica, Padua is not a touristed town

I like the San Terenzo suggestion above. Right on the beach, low key.
Italy can be really hot in the summer so coastal towns like San Terenzo seem much more appealing.

Thank you so much for all the extremely helpful responses!

I think we’ve officially eliminated Siena and Pisa. Adding Verona, Ferrara, San Terenzo, Vicenza, Bassano del Grappa, and Padua. Still very interested in Bologna and Lucca.

Big thanks especially to @hiredman, @Lola, and @nancys8 for the incredibly thorough and helpful responses. Really appreciate the tip about the rental contract oddities and recommendation for the satellite-view-green-space test! Both very helpful!

After listening to several episodes of the Life in Lucca podcast and reading and watching some videos about Ferrara, those two have risen to the top of our list. Still considering some of the other options, but leaning heavily toward Lucca or Ferrara.

Thanks so much for all the insight! It was incredibly helpful. Hopefully after this trip I'll be able to pay it forward and help someone else!

PS- We are aware of the visa requirements, but definitely appreciate the thought! You never know who knows and who doesn't.