Guidance needed for two weeks in Italy ( Rome/ Florence) late December and beginning of January

Not really sure what type of information you're asking for.
Donna

Good idea to limit travel during the holidays. Siena and Pisa are not in the same direction, you may want to consider a full day in Siena and another half-day in Pisa. Keep in mind that days are shorter and so are opening hours for sites. Restaurants will be open on holidays in major cities but you may need reservations, your hotel or apartment owner can help with that. With a family, you may prefer an apartment at least for one of the cities.

I haven't been to the smaller towns in the winter (yet).

Thanks, Donna and Zoe: I'd appreciate opinions as to whether we should focus an extra day in Rome vs. Florence, whether I'm making a mistake to skip Venice entirely, etc. I am hoping people who have traveled to Siena and Pisa (and the Tuscan countryside) in winter could comment as all the information I've found centers on the larger cities at this time of year.

My computer hiccupped and I think my previous reply was sent unfinished. I apologize it if was.
Short reply - Venice is less crowded in the winter, although cold and damp. But, your teens may enjoy the novelty of travelling a city by boat.

I enjoyed Venice in February during Carnevale and would not hesitate to go again during the winter holidays. (Some ladies were wearing their fur coats, but I got by without one.) Rick's cheat sheet summarizes Venice's average high temp in the low 40's and average low temp above freezing.

I love Venice in the winter. It has a totally different moody and atmospheric aura. Yes, it can be misty and dreary, but it might be decent weather... but whatever it is, it's Venice without tons and tons of tourists. You can enjoy it in a whole different way. I would add it if you can. I also like the small towns when there aren't as busy, but I am a photographer so the lack of people everywhere is a bonus for me. I get to appreciate the town in a more quiet way. Just be sure to have the appropriate clothing and you will have a great trip... and if you get cold just think of the trip I had there once when it was almost 100 degrees and there were sweating, sticky tourists everywhere...most who were crabby because it was humid as well:))

Regarding your question about smaller towns during the winter: I visited Orvieto in January, and found a number of the restaurants, shops, and small lodging establishments to be closed for the winter. It worked out for me, since my interests were the cathedral and scenery. But I'd suggest if you are planning a winter visit to a small town, get really specific information about what will be open. That said, I loved January in Rome; it was amazing to enjoy the city without the crowds, and the weather has been mild both times I visited in winter.

This was our trip last Christmas (my boys were exactly that age) - although we did Venice and Milan as well - but our trip was 18 days so it was doable. Not sure what your priorities are in terms of what you wish to see, but with 5 1/2 days in Rome (with two that are holidays) you might be shortchanging yourself on Rome. My best advice would be to determine exactly what you want to see in Rome and go from there. Given your time - I would advise adding an additional day to Rome and skip Tuscany - not that Tuscany isn't wonderful but there is more than enough to do/see in both Rome and Florence given your time constraints. At that time of year the weather can be very iffy - which could definitely impact a day trip to Siena and/or Pisa. Also, you will encounter crowds so you will need to plan accordingly - I definitely recommend arranging for tours ahead of time. I purchased tickets for the Coliseum, the Vatican, etc. ahead of time. When we went to the Coliseum, the lines were quite long despite it being a few days before Christmas! Italy is wonderful at Christmas time!!!!

We were in Rome Dec 22-31, 2011, and traveling in Italy the entire month of December. (We moved here last May). 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 Roman thing to do is have a fish-based multi course feast on the 24th. 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. 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 the holidays approach there will be lists of restaurants open, special exhibits, etc. One blog to watch is Parla Food. Katie always lists great ideas especially for dining.

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.

Tuscany can get snow, especially in the hill towns. Personally I'd stick with two locations and add more days to Rome since there are so many options here. Una vita non basta!

I recommend buying advance tickets for the Uffizi and for the Accademia (David). Lines for these can be hours long.
We recently spent 20 days in Florence and 10 in Rome and never ran out of places to visit in and nearby. Allow a full day for Siena. If you are looking for more, you might want to check out Assisi.

Thank you all very much...I find your suggestions great food for thought!