Venice-Florence-Rome-Milan for 1st trip mid-Dec

Hard to say how weather may impact what you will be doing. First, we don't know what you will be doing? Weather is always a factor especially entering into winter. None of us can predict the weather. You might have two sets of plans with outside activities on one plan and lots of indoor activities on the other.

IMO, you have way too much planned for such a short time. I would skip Florence and the CT and spend your time in Venice, Rome and Milan. As it is you only have 8 full days in Italy. To try to divide it between 5 different areas is too much. You lose at least half a day when changing locations so most of your trip will be spent on the train and checking into and out of hotels. I would cut way back. Donna

I'd skip CT, given the time of the year and add those days to Florence or Venice (depending on your interests). May not be the best time for outdoor activities in the CT. I'd then take a late pm train to Milan, rather than spending the day in Milan, and also add that day to Venice or Florence. Weather is hard to predict, although when I've been in Rome in at that time, the weather was very comparable to San Francisco. Venice and Florence would probably be a little more inclement.

You're all over the place in only 8 days! Agree with above poster regarding taking some things off your list. December is not good weather for either Venice or Cinque Terre IMO, however, Venice/Florence/Rome are "must sees" also in my opinion. Do you already have your tickets purchased? If not, I'd also skip Milan, not much to see there, and just go in and out of Rome to maximize your vacation time. If you have purchased tickets, I would do Venice for two days remember first day will be pretty much a waste {unless you have Ambien on the plane} due to jet lag, then on to Florence for 3 days lots and lots to see there and in surrounding areas like Sienna where you could day trip,
then spend the remainder in Rome and take the train to Milan on the 19th and stay in a hotel close to the airport. Save the Cinque Terre for another time, because it's all about the out doors and hiking/walking, and if it's cold and raining, won't be much fun.

Thank you for the wonderful replies! Tickets are bought, but I'll check the cost of changing flight out of Rome.

Venice in December can be quite agreeable. It can be clear and cold (high 30s), or a bit rainy but warmer. Nothing nearly as cold as an Iowa winter! We spent 6 nights there last Dec and really enjoyed it. We had some cold (needed gloves) but very little rainy weather. Skip the CT. They close up almost completely because it is geared to the outdoors and December just is not the season. Spend 3 nights in Venice so you have two FULL days there. 4 nights in Rome is my recommendation, leaving you 2 nights for Florence. Florence is all about the art and museums. Only you can decide how many days of that is for you. In Venice the city is the show, but lots of great history, churches, concerts. In Rome it's art and history, plus shopping. Since is is Christmas time the lights will be FANTASTIC. You will just want to walk around and see all the lights at night. As others have said, try to skip Milan. If you have to go there for a flight back spend the day in Rome and take a late train (4:00PM or so) to Milan, have dinner, sleep, and leave. Milan is the most likely to have inclement weather.

I wouldn't worry about the weather in Venice. It won't be as cold as Iowa. And it could be quite warm and pleasant. I've been to Italy twice in February and there were days that I didn't even need a jacket. I also saw snow in Rome - but it wasn't really cold, just slushy. I agree, there's little to see in Milan, compared to Venice-Florence-Rome. When you check the fee for changing your tickets, take into account the cost of the train from Rome to Milan. Right now, a super-economy ticket, purchased well in advance, no refund/no change is €39, the regular fare is €89 per person.