I am new to posting and realized that I did not post this the first time under Italy.Sorry for the cross posting.

My wife and I are planning a 1 month trip to Italy about Oct 15th to Nov. 15th. We will fly into Milano go to Lake Como and stay for two nights. We will then plan to travel and spend the nights in the following towns:
Parma, Bolzano/Bozen maybe Castelrotto,Venice, Florance, Vernazza, Sorrento, Naples, and Rome. I was just planning on having reservations for the Lake Como nights,and our last nights in Rome before traveling home. We will be spending a week in the Hill country around Siena area with a car. We plan all other travel by train. My question is will we have problems getting a place to stay if we do not have reservations. I want to have some flexiblity in case we desire to spend an extra day some place. Knowing we may need to cut a day some place we might not have planned on. Where might we have problems with this idea? Will we be spending more time just trying to find a room? Your comments are greatly appreicated. THANKS!

Depends upon your budget and accommodation type to some degree. In large towns and cities (unless there is some special event) you will likely get accommodation in a hotel, possibly at a higher rate than an internet pre-book.

Smaller places may be a gamble, but you are not travelling in peak season (unless you head into the Alba area of Piedmont, where it will be truffle festival season).

Yes, I think you can manage without making advance reservations - especially being off-season. To best do this, you should come armed with a list of places where you might want to stay (along with their phone numbers) and, of course, a cell phone.

I've stayed in places all over Italy without ever booking a hotel in advance. In most Italian cities, there are numerous hotels near the railway station so, even if the first place you try is full, there are others nearby. Of course, if you arrive late in the day, the choices become more limited.
I was once stranded in Bolzano by a rail strike and had to find a hotel for the night (no hardship because it's a very attractive city); the hotels near the railway station looked expensive but I found a reasonably-priced hotel overlooking the bus station.
If you want a room with nice view or other special requirements, then finding hotel rooms becomes more difficult.
Venezia can be difficult, mainly because it's a very popular tourist destination, but also because there are no normal city streets and the hotels are often hidden away. I've used the hotel booking office at Santa Lucia station which will book rooms, but hotels in Venezia are never cheap - the rooms are generally small and are a lot more expensive than in other cities.

Hi B,

Mid-Oct/mid-Nov is off season, mostly.

If you don't want to make reservations in advance, at least make a list of hotels that you would want to stay in in each city/town.

FYI, October is a very busy time for conventions in Rome and Florence. I would book those cities in advance.