How to "split" Italy

Hello,
Your post says you are looking into the future, so that suggests it's not coming up soon. The goods news is that you probably have plenty of time to: peruse some guide books, watch some YouTubes and narrow your 2-3 weeks according to:
what exactly do you want to see? what time of year? What is your budget? Will you drive, or take trains? Lots of things would factor into any responses.
But, as a wildly general suggestion, if you are to spend 3 weeks in the north, you could fly into Venice and out of Milan. In between, numerous places from the Adriatic, to the Dolomites, to the lakes, northern Tuscany and ending in Milan.
If you choose the south, you could fly into Rome and out of Naples, and visit all the fabulous places in the area.
If you mean even further south, encompassing such regions as Puglia, Basilicata and Calabria, that would require a bit more logistical planning.
But it sounds like you have time to do some research, so that your trip will truly be yours, rewarding, efficient and leave you wanting more.

Thanks for your reply and here are more details....
-next year or so
-we love history, architecture (the older, the better!)
-we would like to see some wineries
-we love the smaller cities
-combination of rail and car most likely

If you haven't already done so, you could look at the routings/itinerary for the RS Italy tours to see what/where/how things are grouped and get some general idea of time. Hopefully some inspiration.

https://www.ricksteves.com/tours/italy

DIY will take longer as you won't have the door to door service of a dedicated bus etc.

I agree with everything that's already been said. History is everywhere in Italy, though if by "the older, the better," you're referring to the Roman era (or maybe Etruscan), for Roman you'll want to focus on Rome. Wineries are in many regions, so think about which Italian wines you like the best, and perhaps include those areas.

"We love the smaller cities," I'm guessing that you're not saying that you want to skip Venice, Florence, or Rome (though Venice is actually relatively small), but instead would like to include some smaller cities in your trips. Yes?

For our first trip to Italy, we visited Venice and Florence and points between, spending a couple of nights in Tuscany south of Florence. On a subsequent trip, we visited southern Tuscany, Rome, and Sorrento / Pompeii. We've made a number of trips, to different parts of Italy, since then. But I feel like those trips were good initial trips to Italy.

Italy is my favorite country to visit, and first, I’ll say to make both of those trips three weeks. I will add the link to the trip report when I brought my adult daughter for her first time to Italy (I’ve been there 10 times). We had planned for a 3-week trip for 2020 which of course couldn’t happen. For 2022, she could only get away for two weeks. We had planned to fly info Milan (Malpensa) and begin at Stresa on Lake Maggiore and also stay in Verona before going to Venice - the city where this 2-week trip began.

https://community.ricksteves.com/travel-forum/trip-reports/mother-adult-daughter-italy-trip-aug-sept-2022

You could add time for Montepulciano, etc. in the Tuscany area or head into the gorgeous Dolomite region and save the Amalfi Coast & Rome for the lower half trip, but the Amalfi Coast continues to get even more popular & crowded.

So long answer summarized - if you want a divider, it would be southeast of Tuscany & northwest of Umbria, and you would fly into Rome for your southern trip. (I am considering Sicily a separate trip.)

We have visited Italy several times and it is our favorite foreign country.
In my opinion 2-3 weeks in the north would clearly included Rome, Florence and Venice. Tuscany and Umbria are my favorite areas of the country as well as Rome. Consider visiting Siena, Lucca, Pisa, San Giminanico(sp), Assisi, Perugia, Spoleto and Orvieto.

Verona, Bologna and Milan are worth a visit. Not sure you could do all that I listed in 3 weeks.

As for the South, the Naples, Pompeii, Sorrento, Capri and Amalfi Coast deserves several days.
I haven't been to Sicily, but you could do 2 weeks there easily from what others tell me.

I would definitely make each trip 3 weeks. Longer would even be better. To give you some context as to what is doable, we spent 5 weeks in northern and central Italy last May/June. Our itinerary was Milan, Parma, Manarola in Cinque Terre, Lucca, Siena, Florence, Bologna, Venice, Verona, Merano in the Italian Alps, Varenna on Lake Como, and our last night in Milan. These are all places where we overnighted from 1 to 4 nights each.

I agree that Rome or Tuscany would be a logical dividing line. Depending on your interests, a possible itinerary for the north and central could be Venice, Florence, one other place in Tuscany such as Siena, perhaps the Dolomites, Lake Como, and a night or two in Milan. You could fly into Florence or Venice, and fly home from Milan.

I can't really make suggestions for the south as we haven't been any further south than Rome.

Perhaps a new angle: why not split trips to Italy into western and eastern coasts instead of north and south? If you linger too long in either the north or the south, you start to get used to it - but with this longitudinal variation, things can change (sometimes dramatically) within the same trip.

There is no need to split the country into any arbitrary divisions. You could go to one region ten times and never see everything. Choose where to go based on time of year and other characteristics specific to the region and season.

Dan-love your suggestion! Thanks all for the replies, extremely helpful!

How about this --- it's more about two "chunks" of Italy and two different ways of travel suited to each. Emilia-Romagna and the Veneto together make a really nice chunk that you can do entirely by train. Then, next trip, go to Sicily and rent a car --- it is really helpful to have a car in Sicily. Very different cuisines in these two chunks, and lots of ancient and medieval architecture. Three weeks each would work well. I hope you can travel in the late fall, winter, or spring!

nancys8-I love this!! Really, thanks so much! I am right across the border from you in Wisconsin!

For the Emilia-Romagna + Veneto trip, you could stay in Ferrara, Ravenna, Venice, Treviso. Visit Verona and maybe Padua (my favorite city in the Veneto besides Venice). Yes, it is impossible to see everything, even in many many trips.

I’d suggest 2 weeks may be a bit skimpy.

We’ve been to Italy 3 times as adults. (I will skip the twice as a child). As to N/S divide, we did Rome north followed by entirely the south - no further north than Naples. Let me explain a bit …

First trip: 18 nights in total. Rome Florence Venice, plus Pisa/Lucca, Cinque Terre and 4 days in more rural Tuscany, based near Certaldo. Day trips - Siena, Volterra, San Gimignano.

Second: 18 total nights again. Rome, Florence Venice again, mostly to see what we missed the first time. Plus Orvieto, Padova day trip, Verona, Bellagio, Milan.

Why those big 3 cities and that Rome and North divide for us? Largely because they shared the Renaissance art and history. Smaller cities … Orvieto, Padova, Verona, Siena, as well as Milan share a lot of that Renaissance tradition and art (especially in churches) and some have a bit of the Roman ruins. Etruscan history (pre Roman) in Orvieto and Volterra. Pre Renaissance and late medieval art: Pisa and Lucca.

Third trip: 30 days. Naples, the Cilento, Matera, Puglia and Sicily. Ancient history, Magna Graecia and Rome; Pompeii, Paestum, Agrigento. Later history: Part of the orbit of the Eastern Roman Empire (Constantinople), San Nicola, Arabian influences and Islam, Spanish influence - Kingdom of the Two Sicilies aka Kingdom of Naples. Far less influence of the Renaissance. Influence of Caravaggio’s art in the early 1600s. Did I fail to mention pizza?

Whatever you do, you can never do it all. But if you can do 3 weeks rather that two, it’ll be more satisfying. And I think Rome and North is a sensible divide. LATE NOTE Dan’s thoughts on East and West coasts as two trips and Nancys8 about Emilia Romagna/Veneto as one trip and Sicily (which deserves a two week minimum by itself) as another have lots of merit.

Also, smaller cities and rural areas are a great mellowing agent to include in your travels.

Buon Viagge.

Ive been thinking about this off and on. And after 2 trips (one in 2023 and one this year) I always thought of doing it in 3 or 4 (better) trips.

1 - Rome, florence, naples east to san marino. Basically the center. Easily accessible by train, even for day trips. Lots to keep you busy.

2 North - Genoa, venice, milan bologna, ravenna. Using milan or bologna as a hub you can get to anywhere you want to go in the north. Keeps things within 3 ish hours.

3 south - Bay of naples. There are way to many places to see in this small area alone. But you could also head to taranto and calabria fairly easy if you have 2 weeks and manage to split it. Naples is a great place to base day trips from (paestum, herculaneum, pompeii, amalfi, Capua.

4 - Sicily. Probably impossible to do in a single 2 week trip but mixing it into another italy trip doesnt make sense either. Way to much to see. However if time isnt a problem heading down to Malta is relatively easy.