Hi Nick
Seems a good logistical plan well served by fast trains. At that time of year a focus on cities makes sense - albeit a small question mark about whether Sirmione in winter is something that would appeal?
Is there an option to fly into Milano and out of Bologna (or vice-versa) to save time on transfers?
I’d argue against having a car in Bologna, as there’s a big ZTL from memory, plus the traffic on the ring road can be a bit lairy. Then there’s the train network, which is excellent, plus the city itself rewards good exploration (and the porticoed streets protect against the weather). I suspect the same would be true of Bolzano, and also Milano.
Trento is certainly lovely, and makes enough of a contrast to Bologna that I’d be suggesting it if you weren’t already looking at Bolzano. If Trento were subbed in, there are certainly options to get to ski slopes, or just the lovely old cable car that goes up into the hills from behind the train station… plus Foradori are easy to get to on public transport.
Plenty of wine bars / shops in Bologna, with some wineries in the nearby countryside, but also worth considering a balsamic vinegar producer. On our visit we got a bus out to their winery, where they picked us up to go to the place where they make the vinegar. There are also organised tours.
Certainly a risk of snow up in Bolzano. Aside form that, we’ve just had one holiday that time of year in Northern Italy, and common sense re: clothing and shoes holds just as true there as at home. As well as the xmas markets, do see what else is on (other markets and indeed other events). They can give you a greater feel of embedding in the community, especially for smaller events.
Bologna has a few self guided walks. We did one looking at the old, now mostly hidden, canals. We liked it, as it got us to explore the city, away from where we’d normally go. I expect many tourists might be underwhelmed by the destinations, but for us it was just as much about the exploration.
We’ve had surprisingly mixed results with restaurants in Bologna, and added to that, one we liked shut very soon after we discovered it. In comparison the grazing of food shops there is exceptional, such that we’ll always aim for an apartment. I will recommend sette tavoli on via cartoleria, and imagine it would be lovely and cosy in winter (in the other months we would eat outside on the quiet street). Not sure if they still do the ‘different region each month’ focus, but the food was good, as was the wine list, but there will be fancier places if that’s what you seek.
My gut feel on the skiing, is either you have half of the holiday assigned to that because you love it, or simply focus on enjoying diverse **Italian cities in December. The holiday should still be rich and rewarding without skiing.
I hope this helps
** accepting that Bolzano/Bolzen is just as much seen locally as South-Tyrolian