Family Trip with young kids (Tuscany, Umbria, & Maybe Elba or Sardinia?)

If staying in Florence San Marino is the outlier. It’s also possible that it’ll take another 1h 45m from Bologna so if there’s a place I would see another time, it’s San Marino.
I suggest staying in Florence. You’ll need to read up on ZTL laws to prevent making mistakes, otherwise expect hefty fines when you return home because it sounds like you’ll be driving a lot.
San Marino (3h 15m)
Parma (2h 15m)
Modena (1h 45m)
Bologna (45-minutes by direct train or if driving it can take up to 2h 30m).
Montalcino (2h)
Pienza (2h)
Montepulciano (2h)
Assisi (2h 30m)
Parking can be a hassle especially since you have to park further away so pay attention to where you parked and your kids will definitely be getting a work out.
As far as Corsica goes Paul Theroux wrote about Corsica in The Pillars of Hercules and said the coastline was stunning but definitely was not a beach destination. This is common for the Mediterranean Sea since much of it is a rocky coast.

The part of Italy that has some beautiful beaches is the east side, Puglia or Le Marche.
Have you thought of staying at an agriturismo for the first part of your trip? Many of them are very child friendly.

I have a rule about day trips: not more than 1.5 hours in one direction. A 2 hour journey means 4 hours of driving in a day, too much for little kids and too much for me.

Pienza, Montalcino , Montepulciano, Assisi
The above destinations are in about in the same area.
I would choose an agriturismo (farmhouse) in this area (around Pienza is fine) and visit the area for up to a week. You'll need a car to visit these places efficiently. They are rural small towns with limited public transportation options.

Florence, Bologna, Modena, Parma
These destinations do not need a car at all (actually it would be a hindrance given the traffic and parking restrictions), if you have one it will stay parked all day. The most central of these would be Bologna, but I would stay in Florence (don't ask me why, but my name should be a clue).

San Marino.
This one would be easier if visited from Bologna (train to Rimini, then bus). Not sure this place would be my priority however.

Sardinia/Corsica
Fly from Florence or Pisa or Bologna to Olbia.
I would recommend Santa Teresa di Gallura or immediate proximity. That is where I stay whenever I go. From there you could also take a ferry and spend a few days in Corsica, then return to Sardinia. From S. Teresa to Bonifacio (Corsica) it's only 45 min crossing on a car ferry. Flying to Corsica from Tuscany or Emilia is more problematic (requires changes), so I would fly to Sardinia and maybe visit Corsica via ferry as described above.

Thanks everyone for all the help thus far.

One question still remains, deciding between the mainland of Camogli, Porto Venere… OR going to one of the islands Corsica, Elba, or Sardinia for a week.

If Camogli, Porto Venere, etc.. this could allow us to do more side trips on the mainland.

I don’t want a resort beach town or resort island. Looking for more authentic towns, old villages, good local/organic food. Elba could be the best of both worlds as an extension of Italy.

As far as Tuscany, I don’t want to base in Florence due to the difficulty of parking/driving as mentioned. We have stayed in several agriturismo’s before, and do enjoy them, but also enjoy staying in an small town/village. Either one will be a good option for us. For Parma/Bologna/Modena, we would add a couple extra nights and base around Emilia-Romagna.

Thanks!

One question still remains, deciding between the mainland of Camogli, Porto Venere… OR going to one of the islands Corsica, Elba, or Sardinia for a week. If Camogli, Porto Venere, etc.. this could allow us to do more side trips on the mainland. I don’t want a resort beach town or resort island. Looking for more authentic towns, old villages, good local/organic food. Elba could be the best of both worlds as an extension of Italy.

This is a decision only you can make. My choice would be Sardinia, which is not a beach town or resort island (although there are also resorts). Towns in Sardinia are authentic, believe it or not, real people live there year around. Obviously in summer (very late June through August) there will be lots of vacationers as well. If you go May/June it's not busy at all. I suggested Santa Teresa di Gallura, since I know it fairly well and would offer an easy hop to Corsica as well, but there are a bunch of them you can choose from (Castelsardo, Bosa, Stintino, Alghero, just to name a few in the northern side, are all gems). A week would hardly be enough to visit the whole island (which is larger than Massachusetts and Rhode Island combined), but if you focus on the northern half, you can cover quite a bit, maybe even visit Corsica just for a day (Bonifacio is beautiful) or spend a couple of days roaming around (Alert: Corsica is rather more expensive than Sardinia).
https://www.sardegnaturismo.it/en

Elba is instead the definition of a resort island. It's small and there isn't much to do except for enjoying the beach and diving. That's what people do there, although there are real villages. It's very popular in summer as well. Outside of late June-August, it's quiet.
https://www.visitelba.co.uk/

The Ligurian Riviera is another good choice. It's even busier than the rest in early summer. It has nice villages (Cinque Terre, Porto Venere, etc.). The sea and beaches are nowhere as jaw dropping as the islands, but it's a beautiful scene. Cinque Terre and Porto Venere get very busy in Spring as well.

As far as Tuscany, I don’t want to base in Florence due to the difficulty of parking/driving as mentioned. We have stayed in several agriturismo’s before, and do enjoy them, but also enjoy staying in an small town/village. Either one will be a good option for us. For Parma/Bologna/Modena, we would add a couple extra nights and base around Emilia-Romagna.

If you prefer to stay in a town, rather than isolated in a farmhouse, you can certainly find accommodations in any of the towns you mentioned: Pienza, Montepulciano, or Assisi, or even Siena, if you prefer a larger town. If you want to stay higher in elevation due to high temperatures in Summer, you might even consider nearby Abbadia San Salvatore, on the Mt. Amiata (a dormant volcano). If you go early June or earlier, temperatures shouldn't be an issue

For your days in Emilia, I would consider Bologna over the others. Logistically it's perfect (even for San Marino), being the most important rail hub in Italy. The only draw back is the heat. To me Bologna is even worse than Florence, but Modena and Parma aren't any different. They all sit at the bottom of the Po plain, which becomes a furnace in summer. If you go before mid/late June, then temperatures are ok.

Thank you much Roberto. Extremely helpful

If I may, can I throw another wrench into the mix.
What are your thoughts on ischia?

Maybe even have an itinerary of Tuscany -> Ischia -> Corsica/Sardinia (ferry from Naples) -> Provence (ferry to Marseille) -> Annecy

I keep gravitating towards adding places in Southern Italy, places like Tropea and even Sicily. Most Americans don’t make it past Amalfi. Even with a month plus, this starts to make the travel logistics really spread out as we want to immerse ourselves and enjoy. I know the right answer is southern Italy and Siciliy should be another trip.

Again, looking for a spot that is still authentic and has antiquity
Has a beach (or close), but isn't a beach vacation only destination.
Hasn’t been overrun by American tourists
Local Food.

Thank you again!

Ischia is good.
The only places that might be overrun with American tourists are:
Venice, Varenna and Bellagio (Lake Como), Florence and Tuscany (Siena and the towns in its province in particular), Cinque Terre, Rome, Sorrento and the Amalfi Coast, Taormina in Sicily. Anywhere else you will find very few American tourists, even fewer now with the pandemic still persisting. In Sardinia the only Americans I used to see where the US Navy personnel and their families serving at the Maddalena NATO base, but that was closed in 2008, so I doubt you will see any now.

Thank you Roberto Again, extremely helpful.

I think I've decided to start our trip down in Puglia (Puglia -> Marche -> Tuscany/Emilia Romanga -> Corscia/Sardinia -> Provence -> Annecy

My other task is to keep the trip logistics relaxed as possible with the kids. I assume driving from Puglia to Marche and around Tuscany should be fairly easy. As you mentioned, Emilia Romanga would be the one area to make use of the trains. Ferry to Corsica should be enjoyable.

Instead of Marche, we could do Ischa after Puglia, but makes things a little more work. I figure we could enjoy the coastal areas of Marche.

Maybe my itinerary strays too far away from tourist spots:)

Again, happy to have any input.

Thanks again

Ischia bike maps. Keep in mind yo don’t have to do the whole route.

https://www.bikemap.net/en/search/?distance=0%2C50&center=-97.822%2C37.751&zoom=7&location=3175458

Again, looking for a spot that is still authentic and has antiquity
Has a beach (or close), but isn't a beach vacation only destination.
Hasn’t been overrun by American tourists Local Food.

Responding to the above. I realize you have a month, but the list looks so long, so definitely look at places close to your initial focus in detail. For example, people think Tuscany's coast is only the flat formal beaches like Forte dei Marni, but the south is marvelous.
In late May, the sea can be so cold still. I always travel in late May, and the place I have enjoyed the sea the most was southern Tuscany. I think the seabed may be shallow just off Ucellina park because the water was warm and shallow. We stayed in Pitigliano, Massa Marittima, Vetulonia, and Orbetello. This area is full of Etruscan ruins and natural sandy beaches.
The Marche area is also righfully known for its interior hill towns, but I loved the coastal bit between Pesaro and the Conero area. Senigallia is a stunning old town practically on the beach. The Monte Conero beaches were beautiful, smooth pebbles and clear water of the Adriatic.

I agree about the list being long, even with a month. We will probably have 5 weeks, BUT, I would prefer to stay at least 5 nights at each base so we can really enjoy and do day trips from there.

PLEASE help me EDIT. . For example, Maremma/Tuscan Coast vs. La Marche (Adriatic), delete one and save the other for next time. Again, ideally keeping this logistically as easy as possible while traveling with the kids

Current Itinerary: Puglia -> Marche / Ischia (or neither) -> Tuscany -> Emilia-Romagna -> Corsica (via Elba ferry) -> Provence (via overnight ferry or flight) -> Provence > Annecy

I'd also love to include the Dordogne, but again, that is really stretching things. Open to all suggestions. Trying to combine being antiquity, history, outdoors, hiking, biking, slowfood.

Thanks
Max

Thank you!

PLEASE help me EDIT. . For example, Maremma/Tuscan Coast vs. La Marche
(Adriatic), delete one and save the other for next time. Again,
ideally keeping this logistically as easy as possible while traveling
with the kids

Current Itinerary: Puglia -> Marche / Ischia (or neither) -> Tuscany
-> Emilia-Romagna -> Corsica (via Elba ferry) -> Provence (via overnight ferry or flight) -> Provence > Annecy

All I know to do is write it all out, mapping the route and looking at drive times. The places I mentioned are adjacent to places you already had on your list. I would firm up the France logistics first if that is a must, then work backward.

Thanks. Yes, I'm already mapped out the times between locations.

Was looking for some help editing out a base/location. (For example, Umbria, Tuscany, Marche while different do share many similarities, so maybe the recommendation is just choose one this trip).