1 month mid-Sept-Oct 2026, North/South split suggestions

First, check every iteration of multi-cityflights encompassing every remotely useful airport. Unless you are committed to having a direct flight, you might save some time that way.
The week for Rome/Naples plus is a bit tight. If you flesh out the first two weeks with specifics, you might be able to eke out a few more days.
Some may say don’t go to Sicily without more than a week, but since you have a month overall I think it’s fine.

Hello jen, and welcome to the forum,

I think your schedule looks pretty good but if you want to focus on Rome I would slide some days down to the Rome end of your trip.

Florence certainly deserves a number of days and couple of days in Bologna is easy. Most people here vote for Parma over Modena or stay in Parma and see Modena as day trip. (I'm doing them for the first time next year and staying in Modena because there are places I want to see from there.) I can 5 nights, 3/4 nights, 3 nights being a good schedule and shifting a few days into the Rome end.

The flight days to Sicily require you to stay at least a week, I think. Then a few days in Naples and then Rome for a week or so on the way out sounds good. Rome will eat as many days as you can throw at it. Even with a week there will probably be things you won't get to see.

All of this is inter-city stuff is easy to accomplish by train with the possible exception of you special visit in Sicily. If you can fly into Bologna or Pisa and maybe even Venice you can jump right in. If you fly into Milan or round trip Rome you may have to take a night before travelling on. Some people power onto Florence after landing in Rome but I fly from the west coast it's too long for me to do that. A quick check doesn't show any direct flights to Rome from Boston (summer schedules may differ) which means it should be easier to fly into the north and out of Rome which I would recommend.

A couple of notes: Most people here track nights in places where 4 nights equals 3 full days since it is clearer than what some people say they are spent "2 days" someplace. And it is helpful to track nights of lodging booking as well.
Bologna and Modena are actually in Emilia-Romagna rather than Tuscany. For travel planning it doesn't matter but Italians will call out for misidentifying their region since they are fiercely local.

Hope that helps, come back with city specific questions as they come up,
=Tod

If you can get direct flights either to or from Sicily I would move it to the beginning or end. Otherwise you are giving up two days to travel there.

I think you could steal a few days from Tuscany and add to Sicily and to Rome. For sure I would want a couple of extra days in Sicily. It looks like you are focusing on the west side, but it would be nice to add Ortigia/Siracusa to your time.

Thanks for the advice. It sounds like I need to shift a few days from the north to the south. In terms of a northern home base, would you recommend Bologna? I've never been but have heard the food is amazing (where isn't it amazing?), it's set up well for easy for transportation and is close enough to the other northern places I want to visit. I'd also be open to a more rural town instead that doesn't require driving crazy roads with lots of hairpin turns and has a bit to it (a few restaurants, cafes, etc) while still not too far from the larger cities.

Thank you!

Bologna does give you access to a lot of places: Ravenna, Verona, Ferrara, Modena, Parma, Florence, Padua and Milan are all within about an hour by train.

Bologna has some amazing markets but has so far remained mostly under the tourist radar because they don't have a ton of tourists sites. The city is interesting but it has the University and fair amount of trade shows and other events but the list big attractions is short. The core of the city is super small and walkable, which is good because buses can't really get around the old core of town.

I will say that as good as restaurants are in Bologna I do find it suffers from the "100 restaurants with 1 menu" problem where many places do their version of the greatest hits.

If you are going to be doing a lot of day trips take access to the train station into account with where you stay. As with most cities the area around the train station is not the greatest and nice places near the station are overly expensive. But you might think about bus routes to minimize the back and forth the train station when choosing a place if you choose it as a base.

Have a great trip,
=Tod

Thanks Tod for your input on staying in Bologna. Good point about staying in the train area. Are there any other towns in the Bologna/Florence area with bit more charm than Bologna that you'd recommend? I don't want to stay in the city of Florence since I've already done that 2x. Thanks again!

You mention that your SIL has not been and thus you want to include Tuscany. To me, Florence is in Tuscany but is not the Tuscany a traveler dreams of. (Of course Bologna and Modena are in Emilia-Romagna so another region entirely.) Are you going to Florence for your SIL or do you really want to return?

If you want to do both, how about a few nights (4 or 5) in Bologna or Modena, then a week in Siena? From Siena you can easily visit many more rural and visually stunning towns by bus, train, or car. Not only Florence but Volterra, San Gimignano, and perhaps a day with Tours by Roberto taking you into Chianti. OR take a look at Lucca as a base for Florence, the coast, Pisa.

A week in Sicily is not much, nor is a week in Rome, so pad those locations with as much time as you can. I like them ever so much more than Emilia-Romagna and everywhere has great food!

What hiredman says is true about Bologna

I will say that as good as restaurants are in Bologna I do find it suffers from the "100 restaurants with 1 menu" problem where many places do their version of the greatest hits.

The elusive small town with easy large city train access remains an eternal search. The real problem is that local regionale milk run trains are slow and stop everywhere and you need to get to the big city before you can get to the fast trains. I spent quite a bit of time in Lucca and it is an inexplicable 1:15-1:25 to Florence. So our friends coming from Verona spend about the same amount of time coming into Florence all the way from Verona as we do from Lucca. So while Bologna is only 30 minutes from Florence it is 2 hours (plus train change time in Florence) from Lucca.

That being said the usual suggestions for Florence are Fiesole - a small community a short bus ride from Florence - or places like Pistoia (~:40) and Prato (~:20) are along the Lucca train line but closer. But if you want to be less Florence specific I am only aware of the tourist spots near Bologna. Modena and Ferrara are both about 30 minutes from Bologna. There are also nearby places like Imola - mostly famous for racing - that is :20 by train and looks like you want/expect small town northern Italy to look. I have never been there but it is generally described as pleasant with parks and a good family town but potentially boring when events are not in town. And some place like Imola will certainly be cheaper to stay in (outside of local events like racing season) than a touristy area.

My only caution on going all in on a non-touristy place as a base is English proficiency drops off dramatically outside of touristed areas. Those areas tend to draw the kids that speak English into the hospitality industry and fewer older folks speak English. You can certainly survive in Italy with little Italian and Google Translate, but it does create a layer of separation between you and the people you want to get to know. It is also harder to do things like shop because many places you need to ask if you can pick the fruits and vegetables or they need to do it for you. You can certainly pantomime the action and ask "posso?" or "permisso?" and get a "si" or a "no" but when the answer is suddenly "You can self select whatever you want except for the mushrooms and figs." it suddenly becomes more confusing and difficult.

Just some thoughts, have a great trip,
=Tod

Thank you all for your advice. Lots to think about and consider!

Another thought. Sicily is a bit of a pain to get to from the U.S., whereas Tuscany and Emilia-Romagna are much easier. If you're going to commit to Sicily, then you may want to devote more time there because you're less likely to return. You could include more of Tuscany and Emilia-Romagna in a subsequent visit to Italy. (We were coming from western U.S., so ended up flying to London, spending the night there and visiting a friend who lived in London, then flying directly the Palermo the next day. At the end of our time in Sicily, we flew from Catania to Rome. It was definitely like fitting puzzle pieces together, getting to and from Sicily and planning the rest of the trip.)

If you do decided to cut back on your time in Tuscany / Emilia-Romagna, I would suggest one or the other area - they are both fabulous, though I will say Tuscany is more gorgeous and Emilia-Romagna has better food. And I too love Siena; we've stayed there several times as a base city for the area.

We spent two weeks in Sicily, and I could have spent more time there. It depends on your interests, of course. We love mosaics and Roman and earlier ruins, so those were must-sees in Sicily for us. But I also love Rome, Bologna, Modena, Tuscany, and Emilia-Romagna.