Question-Would it be crazy to just head off from Venice without reservations between there and Rome and take our chances finding places/accomodation along the way? Or is Italy so busy in September that doing so would be a huge mistake?

September is "highest" season in Italy.

Are you driving or taking trains? If you are driving, you can probbly always find a room at an agriturismo, but it will be time-consuming, since many of them are not on the main roads; you have to look for the signs with arrows that say "agriturismo" and the name.

If you are traveling by train, most of the stops will be in cities or towns with large numbers of tourists. You'll find a room but, again, it will be time-consuming.

I would at least travel with a longish list of accommodations (with telephone numbers).

Huge mistake at that time of year. Unless, of course, you want to spend 20 percent of your vacation time running into hotels and asking if they have a room and then asking if they have any recommendations for what other hotels might have rooms. You probably won't end up sleeping on a park bench, but you'll cut down the amount of time you actually get to enjoy your vacation significantly.

If your idea of a great vacation is not caring about what kind of place you stay -- happy with the only place in town that wasn't already booked by the people who do care -- and you enjoy spending your time looking for a place to stay rather than enjoying the sights --- then yes, that's a great idea.

If you want to stay in a reasonably central location in those cities in September without reservations I would assume you have an unlimited budget - since finding clean, decent properties at a reasonable price is hard enough searching months in advance.

In fact, you've left things quite late to even find places to book ahead.

I'll be in Venice in October. I started looking for hotels in April and was surprised how many were already booked 6 months in advance.

Hi T,

It's 6 hr by car, 4:30 by train. Where were you planning on stopping?

Illogical.
Busy season+very popular vacation destination=few good rooms available
How much time do you want to invest in looking for a place to stay?
Do you speak Italian?
If driving, why are you driving?
If training, how do you plan to find a place as you shlep your baggage with you?
If it's this year, you already will find most prime places booked.