Italy in December

I recommend to visit the cities since the countryside and the small villages will be dead in December and also not that enjoyable because of the weather. Cities always have something to offer, indoor and outdoor, regardless of weather conditions.

Since this is your first Italian trip, I recommend to start with the top 3 city destinations (Venice, Florence, Rome, in this order). Florence is also an excellent base for day trips to other Tuscan smaller cities and towns (Siena, Pisa, Lucca, Arezzo, Cortona, Pistoia, etc.), so you may want to stay in Florence a few extra days for that (Florence itself deserves at least a couple of days).

Don't bother with coastal destinations like the Cinque Terre in December.

If you can find an open jaw multi-city flight with arrival at Venice-VCE and return from Rome-FCO that would be great, as it would save you some back tracking.

I think winter is a wonderful time to experience Italy and even the big cities are less overwhelmed by tourists. We spent 4 weeks traveling in Italy in December before we got lucky enough to move there. It was a terrific month with little rain and we thoroughly enjoyed Venice, Umbria, Sorrento and the Amalfi Coast, and Roma. December 8 the Christmas lighting traditionally begins and ye you will not be overwhelmed with Christmas music. It's nice.

Will you be there over Christmas and New Years? That requires some special planning but also adds to the experience. Let us know so we can be more targeted in recommendations. Exactly how many nights will you have in country?

I, also, was a teacher when we took our first trip to Italy in 1984, during my Xmas break. It was great. We did Rome, Florence, and Venice, with a short stop in Siena on the way back to Rome. We had a car, gratis from the airline; but you not only don't need one, it would be a real burden. (In those days, the airlines actually competed for customers by offering such incentives.)
With just two weeks you can hardly do more. A day trip to Verona or Padova from Venice could be possible if you allot enough days there. Depending on your home airport, you may be able to fly open jaw, into Venice and out of Rome. That would save more time for touring.
Don't expect to see no crowds. Even in cold, gloomy Venice with the gondolas shut down, there were plenty of visitors from even colder places. And, after all, Rome? Christmas? One wonderful feature of the season is the Christmas decorations in the churches.
Weather, of course, is unpredictable. We had good weather, for the most part, just some cold and rain in Venice, cold meaning down to the 30's at night. However, you should be prepared for winter. A hat, gloves, and a scarf take up little room and go a long way towards keeping you comfortable.

Thanks for the replies thus far. Good to be prepared for both weather and some crowds in Dec but this gives me hope about our decision to travel in off season.

To go back to Laurel's questions: we do plan do be in Italy for both Christmas and New Years. And we plan to take the train as much as we can to minimize the need for a car.

Please keep the suggestions coming!

We were in Rome for Dec 22-31 one year and traveling, as I mentioned, in Italy the entire month of December. (We later moved there and spent several winters, 2012-2016).

The 24th - 26th take some planning, but there's plenty to do. The 24th we spent the morning at the Borghese, shopped, had lunch, rested up, went to church at 6:30PM, then dinner at 8:30, followed by a nice walk to see more lights. The city is so decked out at Christmas! A very nice day. FYI, by afternoon most sites were closing.

A very Roman thing to do is have a fish-based multi course feast on the 24th (reserve in advance).

The 25th we cooked a nice American breakfast, then took a walk through the Ghetto where it was pretty much business as usual. Lots of people were out and about . The ghetto was a great choice for dinner, too, but make a reservation because a lot of Italians dine out for Christmas! There are two precipi (nativity scene) museums open on Christmas Day so we visited one in early evening, taking in the lights at Piazza Venezia as well. The 26th we took a self-guided walking tour up the Gianicolo to Villa Doria Pamphilj, then toured the Palatine and Forum in the afternoon. It was in the mid-60s and sunny! We were exhausted! The point is, with planning, there is plenty to do even if some sites aren't open. Just walking (check out the book "24 Great Walks in Rome" for ideas ) is entertainment. .

As to accommodations, we rented an apartment near Campo dei Fiori and it was perfect! Great to have a small kitchen, washer, and space to hang out. I think this is particularly important over a holiday with a whole family.

Also, take a look at http://www.italylogue.com/planning-a-trip/everything-you-need-to-know-about-spending-the-holidays-in-italy.html.