I have all of January off and have been thinking of spending time in Italy most of that month and the real question I have is where I shouldn't bother going during that time of year, if anywhere!
Joseph,
As someone else mentioned, unless you enjoy winter sports it probably wouldn't be advisable to go anywhere in Italy from Rome and north in the winter months. However, Sicily and the south will be a bit warmer but you should still allow for 'layering' with clothing.
Another area you might consider in the winter months is the Algarve in Portugal. The temperatures are usually consistently decent in the winter, with temperatures ranging from 15 - 19ºC.
Happy travels!
As previously noted in another thread, there are a few places in Italy that probably are not as 'wonderful' in January. That isn't to say you shouldn't go there, but that they are better at other times of the year (YMMV).
Venice is one--far enough north to be colder, & a higher risk of flooding. I would not bother with northern Italy at all, unless I enjoyed winter sports like skiing, which I don't. This excludes Milan and the northern Lakes.
Cinque Terre may be worth it, although I hear it's not as good as other times of the year.
Also, many of the small back road villages will be quite dull--for instance, Rick says that one of his favorite towns, Civita and Bagneregnio (I think I spelled that wrong), is completely quiet and dull in the winter, and recommends side-tripping in quickly from Orvieto or skipping it all-together.
On the whole though, if you love Italy as I do, there really isn't such a thing as a "bad" place to go. If you want warmer temperatures, stay to Rome and the south. Florence was about 5-10 degrees colder in December and you definitely notice the difference!
I also wouldn't bother with Venice. Frankly there is little charm in rain and ankle deep water,, LOL
I would go to Rome, there is so much to see there, and having only gone in the heat of summer, I can say I would rather go in the winter next time. so much to see, and being broiling hot makes it unpleasant.
Claire lives in Italy and she and Ron say the same thing about Italy in January: it will surprise you with how cold it can be, both outside and inside. Outside because of the wind and inside because they don't use heat the way we do here. Here's Claire's description of the cold, the 5th post down in this thread: Italy cold in January