I am not sure where I will be headed after December 27th...Bologna, Milano, CT??? I will be driving, thus want to know if I can get a room on the spur of the moment??
That is a tough one and you would need some direct experience to answer well. I can come close for you. We spent the week of New Years in Spain last year. Since there was four of us traveling and needing two rooms, we booked everything ahead. We were in Madrid, Cordoba, Seville, and Granada. At each hotel I checked to see how full they were. Only the hotel in Seville was sold out but it was over New Years eve and day. And it was our smallest hotel with 15 rooms or so. My gut feeling is that you could always find something. But it could be more difficult that week.