Hi All. I am planning a third trip to Italy and have spent a decent (never enough!) amount of time in the country. This trip, however, will be a little different. We are planning to come in the real off-season - early December. I am hoping to spend a couple of nights in a couple of different Tuscan towns/villages after flying into Rome. We don't need nightlife obviously but do want to be able to get a nice meal. Are any villages/towns better than others for this time of year? The cold doesn't bother us. We plan to head to the Como area afterward before traveling on to Switzerland for some early season skiing in Zermatt - if there's no snow we will just sight see. I have similar questions for Como area - any places better or worse to stay at this time of year? Anythings we won't be able to do due to the time we are planning to go?







All of this is pretty preliminary at this point and not at all booked or reserved. Unless I get a lot of feedback saying, don't do this at this time of year, I would like to take this trip in 2020. That should give us plenty of time to plan.







Thanks very much in advance for any and all feedback!!

I can think of some small cities and towns in Tuscany that I would enjoy in December. Arezzo is the first that come to mind, and Siena has a lot of fans here. From there you might want to venture into the Tuscan ski areas, although I'm sure it's very early.

If you're wine lovers, I would pick Montepulciano over Montalcino and the Chianti towns, simply because it's larger and livelier. Prato and Pistoia?