Italy for a one month long stay October 2025 -

Verona and / or Vicenza. Perhaps two weeks in each? Good rail transportion, good food, good architecture. and not overrun with tourist. Lots of places close enough to do day trips. Just one opinion.

You haven't been to Florence. It is an amazing place and deserves several days.

You could stay in Siena, near Florence and take day trips throughout Tuscany.

Another choice is to explore Umbria and stay in Perugia, Assisi or Spoleto.

I don’t see Ravenna on your list. In my opinion, it is definitely a must-see. The mosaic sights are mind-boggling beautiful. The town, itself, is very attractive, with a pedestrianized historic center. Staying at least one night would be preferable to a day trip, as there are a number of sites, somewhat spread out.

I would choose Bologna for ease of transportation to other places and amount of stuff to do and places to eat in town. I also enjoyed day trips from Bologna to Ravenna, Parma and Faenza. I would have also gone to Modena or Ferrara if I hadn't been dodging train strike days. I could have happily spent an extra day in any of my daytrip towns, but for a month-long base, I would choose Bologna.

I vote for a month in Emilia-Romagna!

Wonderful food, interesting places, easy to get around by train.

Bologna, Modena, Parma, Piacenza, Ferrara, Ravenna, etc. and Mantova nearby too (technically in Lombardy).

We were just in Northern Italy and loved it!

Bologna was one of our favorite spots. Food, history, architecture, walkability - all great!

We also went to Verona, Padua, Bergamo and Varenna.

Verona - Super walkable, charming, good shopping, Roman sites, Romeo and Juliet connection. Second favorite after Bologna.

Padua - Bigger city, great cathedrals.

Bergamo - Stay in old town area within walls, walkable, scenic hill town.

Varenna - Lake Como, take ferries to other lake towns like Bellagio. Very pretty area. Not sure what the weather would be like in October.

Enjoy!

Before you decide to stay in Bologna, check if there is a major trade fair as hotels will be heavily booked and rooms priced higher than usual.

I just got back from a trip that included a month in Lucca and it was an interesting experience. My criteria was basically small Tuscan town life without some of the drawbacks of real small Tuscan town life - flat, train access, larger city around etc. - and Lucca was a great choice for what I was looking for. Some place like Verona could be a good choice or Bologna or you might consider Brescia. I've only been there briefly but it is much less touristy and would certainly be cheaper and it is on the same fast train line as Verona and Padua.

The advice to check the schedule is a good one. Lucca has a comic-con that swells the population of the town a ridiculous 8x and we specifically shifted our time to avoid it due to the renting difficulty since that weekend people can charge huge rates - same issue with beach towns in summer. Verona has opera in July and August and Bologna has events plus it is a college town so renting while school is out could be real possibility but looking for a longer rental right after school is in could be an issue.

Having just stayed in one place for a month one of my concerns would be getting into a situation where you're renting something sight unseen and it turns out not meet your expectations. AirBnB has erased the longer vacation market for real estate agents in Italy so you probably won't find anyone willing to work with you for such a short term rental. So you're likely stuck with AirBnB, VRBO or Booking.com as your only real choices. I reached out to a realtor based on an article he wrote on Italian rental terms and issues and he referred me to the rentals specialist who just sent me AirBnB links. All the sites I found that advertised longer term rentals received no reply or "We don't do that anymore but if you want to rent for 1 year+ or buy let us know."

I would also recommend learning some Italian. It is not required to generally get around but sometimes it really helps when you really need something. It also really helps if you are trying to live somewhere and experience being part of the community. Italians love to talk more than anything and if you can't talk with at all it really leaves you outside the main social function.

I would try and articulate the experience you want and then develop a criteria for the place you think you could best find that and then start from there in terms of a town search. If your time is set than that might very well narrow the list and budget might figure in as well. If you want more details on my stay hit my on a private message. I may do a trip report in the future since people seem to have the same kind of idea about longer stays.

Hope that helps,
=Tod

Verona has some wonderful sights but there are some troublesome teens hanging around various places. It's not a bad location to branch out to Bolzano and the Dolomites, some of the lakes, and maybe Bergamo. In fact you could even get into Austria through Bolzano.

I was just in Florence recently and it way way way too nuts with tourists everywhere. I would avoid there and Pisa.

With Siena and Tuscany you probably need a car to hit the many other hilltop towns. Siena is a tourist magnet too.

We really enjoyed Bergamo's upper city - nice city walls to walk with great views, nice restaurants.

There is also the Ligurian riviera with many improvement over CT.

Lucca is ok - big (but ugly) city wall, interesting round center - but otherwise not exciting.

If you want to go to Puglia, Bari is a very reasonable larger city which is not touristy and has a variety of attractions - including ferries across the Adriatic.

I would also recommend learning some Italian. It is not required to generally get around but sometimes it really helps when you really need something. It also really helps if you are trying to live somewhere and experience being part of the community. Italians love to talk more than anything and if you can't talk with at all it really leaves you outside the main social function.

This is true everywhere, not only in Italy. I spend my holidays in Austria and I observed that understanding and speaking a little German - just a little and nothing too literary - goes a long way, not only in interactions with locals, but also being much better informed about what is going on around and knowing about local events not meant for tourists. [Just for example, in Salzburg there are reduced car park rates for people buying in some central shops, but the thing is advertised in German only].

Thank you for all the great suggestions so far! I’m really taking them into consideration.
I’ll give you a little more information about us which might be helpful in adding to any of your comments or new comments.
We have been to Siena, Florence and Orvietto as well that I didn’t to mention previously. We love Italy!

We like monuments, history and occasional museums, but also enjoy hiking, culinary exploration and photography. We are in our early 70s but active and fairly seasoned travelers. We really enjoy getting to know the locals. And you’re right -speaking the language can be really helpful. We speak a wee bit of Italian and Spanish which has gotten us by. And thank goodness for Google Translate. We’ve had some fun with that with people! I find that they really appreciate that you are at least trying, and not expecting them to speak English -in our case.

Regarding the Airbnb’s Tod /Hiredman, (we are from Oregon, so hello neighbor) Thank you for the reminders about checking into the long-term rentals and changes. I know that there are areas that are not as open or are clamping down to rentals like Airbnb because of the difficulty the locals are having in finding living arrangements. Or just too many tourists.
Just as an FYI that might be helpful to others, when we look at an Airbnb we do a really deep dive into the reviews. We look at the photos carefully and if there are windows, we try to see what the views are outside such as which floor they might be on, whether it’s very urban or industrial etc. Also if we can see a street sign if they show outside views, or specific shops we will look it up on Google maps and drop a pin and “walk” the neighborhoods. For us we don’t mind walking up three flights to get to our apartment, but we’d draw the line at bedrooms and bathrooms on different floors. Just not something we want to deal with in the middle of the night. Also we cook most of our meals at home, so a well equipped kitchen for a long stay is essential for me.

Considering the location to stay for the month, I am beginning to feel that maybe Bologna might be too big.? The comments about Verona having troubles with teen groups doesn’t fit with what I’m looking for, but all larger areas probably have something.

I’m wondering if anybody has any feedback on the Modena area?
I’ve heard lots of good things about Lucca but is it pretty far removed from what I’m thinking about for the autumn food/festivals and culinary experiences? Again we’d really like to have a town that is pretty walkable but has train access for those quick getaways.

October can be beautiful. I am so sad about the flooding that has taken place in the Bologna area and throughout Europe. We can’t predict the future but hopefully that is not the trend for these areas.
Please keep the comments or updates coming, you’re helping me determine which spot to call home for a month. Thank you so much!