Welcome to Slow Travel, NLarimer!
We all experience some trepidation, maybe even a bit of anxiety before a trip, any trip, not just the first one, the first vacation together, all full of symbols, of course.
The main thing is to concentrate in what you would like to do.
Winter extends over a long 3-4 months, with a miriad of variations from region to region, and even within the same region there are wide fluctuations due to the fact that they all have their own micro-climates.
You could centre your trip on the South of Italy, inherently warmer.
I would suggest first that you arm yourself with a few Italy travel guides (for this initial purpose any of them would do), and maybe do some reading of a long gone author, H.V. Morton, specifically his "A Traveller in Italy" and "A Teaveller in Southern Italy". They will be a wonderful introduction and almost surely help you to narrow down your itinerary.
Our web site
www.slowtrav.com has a wealth of planning resources and you could start from the Italy section by clicking
here. Ask questions; we will always be happy to attempt to answer.