Italy in November/December

If you intend to travel at that time of the year, it is better to start from the north (Milan) and end your trip in the south (Rome) where the weather is more amenable in December.

Milan: 2 (3 max) nights are more than enough for Milan, at least for me. If you want to take just a day trip to Lake Como (Varenna) you can add one night, although I’m not sure about visiting the lakes in November. See what the weather looks like then decide. Milano to Varenna is a 70 min train ride. Or if you plan multiple days separately at the lake (see below), then 2-3 nights are plenty for Milan.

Lakes: lake Como is the closest to Milan. The weather in November is a big “if”. 3 nights are probably sufficient.

Dolomites: 4 nights are fine, not sure if you plan to drive a car or not. You might need one in this area. Snow is a likely possibility in November, near certainty in December. Cars must carry chains or have snow tires after Nov 15 nationwide in most roads. Cold! Visit Castel Brando on the way to or out of the Dolomites.

Bolzano 2 nights is ok. You have time for Merano as well. You can couple this with the Dolomites (before or after). They are close.

Verona needs a day, so 1 or 2 nights are plenty. If you want to see Venice try to find 2 or 3 nights to spend in Venice rather than just a day trip from Verona. It’s worth it.

Umbria. 8 nights for those small towns is a lot. Borrow some for Venice above. You probably need a car for those day trips, especially if you stay in a small town. If relying on public transport stay in Perugia, Umbria’s regional capital. Also I don’t know how Brisighella ended up in this group. But if you must go to Brisighella, do so from Bologna. It’s much closer.

Bologna. To visit what you want to visit you don’t need a car at all. Much easier by train. You need a day to see Bologna, so a night or two is sufficient. Add a night for each day trip from Bologna.

Florence: 4 nights is good, but I’d borrow more if you plan lots of day trips. Florence is a perfect hub for day trips throughout Tuscany, by train or bus. Florence alone needs at least 3 nights.

La Spezia: why? Is your husband interested in joining the Navy? Or you just like to see ugly industrial port towns? If interested in the Cinque Terre just stay in one of those villages a night or two. Just be aware that the Cinque Terre are pretty dead in winter and the trails are closed after the first rains.

Rome. 5 nights with a day trip is adequate. Rome alone needs 4 nights (or more).

Put all the place you listed on a map.

Then connect the dots. If the result seems an abstract painting overlaid on the Peninsula there is something wrong.

I'd Stay in Venice and make a day trip to Verona. Venice is a unique, floating city teleported from the 18th century; Verona is an overrated, polished tourist trap.

Since you are interested in food, check if / when Slow Food will held its International Autumn Fair/Event in Turin. As a side note, the Langhe wine country is loosely located between the Cinque Terre and Milan and food is almost a religion there.

I don't know what your interests are, but if you like cathedrals, you must go to Orvieto. I think it's in Umbria.

Congrats on the Phd's! Roberto has made some excellent suggestions & I would only add that Pompeii is not my idea of a pleasant day trip from Rome. Others on the Forum have done it, usually because it was all the time they had available. December can be lovely, especially at lower elevations near Florence, (I've hiked 3 days outside Florence in Dec, even had a bit of light snow, we were warmly dressed), but north of there the weather will be very ify. Personally, I would skip the Dolomites at that time of year, too early for skiing, too late for comfortably hiking, and add Sorento / Naples for the archeological museum & day trip to Pompeii & Herculean. AND you mentioned food as a deciding factor - Naples has wonderful food, maybe a food walking tour to sample it's delights? I would also skip the northern lakes in December, you might have great weather but more likely not. We usually give ourselves city / museum alternatives in case of increment weather.

Congrats! How nice to spend three weeks in Italy. We have been there in late Oct & early Nov last year and in Sorento & Rome in late Dec a few years ago. It was a great time to visit. You are moving around a lot and it can get tiring. Every time you move you lose at least half a day.
I would suggest some of the food and/ or wine tours. Also we loved Orvieto & Siena on our recent trip I did not see them mentioned.
Enjoy

As to the Dolomites, not an ideal time of year. November is decidedly off-season and ski season starts in early December. The villages are prettily decorated for Christmas but hiking, especially at higher elevations, is hit or miss based on the lift schedule in the area you choose.

I would spend time in Venice, at least 4 nights. Daytrip if you like to Verona, but Venice is not to be missed nor rushed. We actually like is best in the winter when there are no cruise ships docking.

As another responder queried, why La Spezia? Doesn’t make sense unless you have a special reason and it is “off piste” so to say, from the rest of your plan.

The lakes do not make sense at that time of year. Most services geared to the traveler are closed, including many hotels. Cities make the most sense in November through February unless you ski.

Thank you all so much for your suggestions! You've given us a lot of food for thought! Time to revamp the travel spreadsheet :)

My husband's grandparents immigrated to Australia from La Spezia. Unfortunately, they've passed away, but he still has some distant relatives in La Spezia. We thought it might be nice to go and visit where his grandparents grew up as it's not too far away from Florence.

Congratulations on graduating. What a great way to celebrate.

We’ve been to Italy multiple times. The best trips have been the ones where we stayed in a place for 5 or 7 days and then took day trips by train. We loved Verona and Bergamo, both are which are worth several days and are good bases. So are Orvieto, Padova, Parma and Spello. Each is different and worthy of a visit of several days; even a week IMO. Of course Rome is a must-see! You could spend days there. Depending on your interests, same for Milan— the Cathedral takes a full day.

I do agree with the poster who suggests starting north and ending up in Rome in December. Northern Italy gets pretty damp in the winter. (Don’t be discouraged though. It has its own charms every season.)

That being said, I suggest you identify several towns to use as bases and then plan a couple of day trips from them.

It’s a wonderful country. Take your time to just wander, meet interesting people, go to local markets and cook some pasta, and find the best apertivo and gelato in each town! Have fun!