Tuscany - Emilia Romagna - Veneto in June

I'm confused:
Do you want to stay in Milan, or do you want to head toward Parma, Modena, or Florence upon arrival? You probably want to get at least as far as Florence the day before needing to be in the small village.
Are transportation arrangements for the Mercatale Valdarno part made?
I don't understand braking up the Venice part--I would instead go to the Dolomites and then Venice last.
I would try to reduce the number of one-night stays.

I'm sorry if I confused you.
We do not need to stay in Milan - but certainly would if there is good reason to (I do not know how difficult /time consuming it will be getting to the train from MXP, while jet lagged).
No plans to "do" Venice before the Dolomites - but we know that is a good spot to rent the necessary car. We've been to Venice before, so don't feel the need to block days for it.
The family celebration is a definite as is visiting relatives in the Dolomites. We prefer to NOT change hotels each day, but rather every 2-3 days. We are asking for advice on good locations, and activities, to try and flesh this out before we make hotel reservations.

I just think you need to answer those questions before proceeding--have you been to Milan or the others? Milan, Florence, Parma, and Modena are all very different. I would choose the one that is easiest to get to from MXP and from there to your Mercatale Valdarno stay. Milan is obviously the easiest to get to, but if you do not have any interest in staying there, it is easy to hop on a train.
Cars are reportedly very expensive this year, so I would decide soon, good luck!

It seems like you have a lot of sleeping place changes. Have you traveled like this before? It's a lot of overhead, with check out, driving, parking, checking in ... . It's also unclear how many drivers there are. I haven't been to Parma or Modena, but are the stays in an urban or rural setting? I mainly ask because seniors on their own might benefit from a chance to get up early and WALK around a city with things to see and do. It's a modern small city, but I enjoyed Reggio Emilia a lot when I was there on business. And we took the train back to Florence from there once, for an event we found out about the existence of during our three nights in Florence.

Yes, I recognize the last few day may have to be in new hotels each night (depends on the relatives' schedules!), but otherwise, we are asking for input on WHERE is a good place to base ourselves the first week. Hopefully we can stay in one place and enjoy it, and maybe take a day trip to another small town. We do not plan to rent a car except near the end of the trip to get to the relatives.

As stated above, we want to spend time in smaller cities/towns. We have been to Florence & Venice and do not need to spend time there on this trip. We are looking forward to hearing suggestions about the merits of Parma, Moderna, Bologna, Ferrara, Ravenna, someplace outside Venice (stayed in Padua already) - and then we can pick where would be best to sleep and for how long. Thanks!

For the first few nights, I would sleep in Parma if you want a smaller town feel. It has a lot more to offer than Modena and I don't see the benefit of spending a night in Milan only to go on farther south. On June 2 I would vote for Ravenna. It has the most sights and the most charm of the three options. Outside of Venice, since you've already been to Padova, you might try Vicenza for a smaller town. I don't know what the rental car options are since I've never done that from there, but it's very easy to get to on the train.

Following this thread with interest because I am trying to decide among Modena, Reggio Emilia, Parma, and Bologna as a home base for 7-10 days later this year (without car).

Accidental, I stayed in Bologna for 7 nights this summer and used it as a base to visit Parma, Modena, San Marino, Ravenna and Ferrara all by public transportation. I would highly recommend!!

Thanks Bill! I sent you a PM

Another vote for basing in Bologna. Best transportation options in all directions, by far, and one of Europe's largest medieval centers.

Although it doesn't get large numbers of foreign tourists, it must see a lot of Italian visitors and business travelers, because lodging can be really picked-over if you start looking shortly before your arrival date (my usual modus operandi). Don't choose a place near the train station; that area's not nearly as nice as the historic center.