Itinerary ideas after the f1

Been to Bologna, it was OK, but not that impressed.
We loved Ravenna.
Siena and Lucca are worth a day each. Also, San Marino is interesting, but not near the top of my list. Consider Umbria (Perugia, Orvieto, Assisi, Spoleto)

Thanks I did wonder re Bologna and Lucca was on the list then came off etc. Wondering whether picking a car up in Milan and making our way down gradually via smaller places may work? We decided not to do Umbria on this trip as I think we will be back to Italy a few times etc

We’ve don’t city/ road trips in Portugal the last few years lol. Any opinions on Ferrara, Modena and Parma?

I think Bologna is a great transportation base for visiting all the surrounding places you mention including San Marino. I've stayed in Bologna and enjoyed it, as have many others who post here, and I know two couples who separately used Bologna as a base for month long visits to Italy and don't regret their decision. It's easy to day trip by train to Ravenna, Modena, Ferrara, etc. For San Marino, the couples took a train to the nearest station and then a taxi from there. You could rent a car and make multiple stops, but frequently changing hotels takes up a lot of time. I'd suggest sticking with your plan for two bases with good access to the places you want to visit, one in Emilia-Romagna and another in Tuscany or Umbria.

"Any opinions on Ferrara, Modena and Parma? "

I liked Modena, really liked Parma, and really really liked Ferrara. Ravenna not only has the famous mosaics (which are definitely worth seeing), but is a nice town to boot. so, all of these are great ideas.

I didn't like Bologna, but I'm in the minority. If you aren't driving, it does make the easiest base for seeing all the other places in Emilia-Romagna. If you are driving, you will probably want to stay somewhere with easier driving and parking, and day trip in to see Bologna.

Closer to Milan, also investigate places like Cremona and Mantova.

Are you sure you want to spend a night in San Marino? There doesn't seem to be much to see or do there, except to be able to say you've been to this micro-state. I haven't been, so maybe it's an undiscovered gem - but nothing I've read or seen indicates that.

So I think we are sort of there but could do with a bit of feedback and poss some hotel suggestions...

6 f Arrive

7 s Milan Grand Prix
8 s Milan Grand Prix
9 m Milan Milan
10 t Travel to Bologna Bologna
11 w Ferrara Day trip from Bologna
12 t Ravenna Day trip from Bologna
13 f Parma or Modena? Day Trip from Bologna
14 s Travel to Florence Florence
15 s Sienna Day trip from Florence or rail and stay in Sienna??
16 m ????
17 t San Gimiglano and Volterra organised day trip from either florence or sienna rather than hire a car????
18 w Castell Gandolfo organised day trip from rome rather than hire car????
19 t Rome

20 f Rome

21 s fly home

So still a few gaps and after some advice on whether to do day trips organised or not and/or hiring a car etc and also one missing day. So any ideas suggestions/recommendations gratefully received

maybe the alternative to using bases and day trips is alternate hire car itinerary from bologna to taking in pistoia, volterra and san gimignano, sienna, orvieto down to castell gandolfo maybe with a few other stop offs? what do people think?