8 nights/7 days in October - is this too much to try and do?

In my opinion, yes. Italy is best when you allow yourself time to savor it. You will be moving around as much as sight-seeing. I personally wouldn't do more than 2 big cities or maybe 3 smaller cities in Italy in 8 days. You could spend the entire time (and more) in Florence and the countryside, or in Piedmont, or in Milan and surrounding areas. It's just up to you whether you want to see a lot but not much in each place, or less places but delve into them a bit more deeply.

If that is all the time you can possibly manage and those are the places you want to see, then go for it...Yes, it will be a whirlwind 'taste of Italy' trip, but at least you have 2 nites in each place. I've definitely done plenty of trips like this, and while I would prefer unlimited time and money such is not the case. If you are getting a car, it will be pretty useless in CT, Florence and Siena and probably more of a pain than its worth. If you want to stick with the car (which I typically do, especially in Tuscany, I would not stay in Siena and I would figure out the logistics for CT. I have driven there a few times, but also taken the train from LaSpezia as well as Alessandria, and train trips were definitely more enjoyable.

Thank you both for your replies. It does seem that we will be moving more than sitting if we try and do too much. I think the plan is to take a train to Florence and pick up a car and then we may just focus on Siena/Florence and Cinque Terre areas and skip Piedmont altogether. If you have any suggestions on nice, off the beaten path lodging alternatives in either area I would be grateful. Thank you - Jason

I kind of travel like that, so it sounds ok to me but. I would try and stay another night or two in the Tuscany area. Florence is worth a good day and a half and so is Sienna. Florence has the art but Sienna is more charming.

Hi Jason
We just got back from three weeks in Italy and had a fantastic time. With a car you would do best to base yourself in the outskirts of Siena at an agritourismo and use the car for exploring the small towns and wineries nearby, Take the train or Sita bus into Florence and do a long daytrip there (Florence with a car is a major pita). If you're planning on going to the Ufizzi or Academia prereserve your spots and work the rest of your day around either or both. (Keep in mind that a lot of the museums are closed on Mondays.)

Thanks for all of the replies. I think we have decided to do either Tuscany + Cinque Terre or Piedmont + Cinque Terre do give ourselves more time in each area. We are not planning to do Tuscany + Cinque Terre + Piedmont. Not enough time. We can't decide on Tuscany or Piedmont. Would enjoy some thoughts on these areas - seems Siena is extremely popular but don't hear too much about Piedmont. We are more interested in scenery and experience over the museums. Wine is also a huge motivating factor. Sightseeing isn't our thing as much. I realize a car in some areas (Florence, Cinque Terre) is either not advised or not possible but we will figure out a way to incorporate a car and park it where we can. Thanks again for all of the great suggestions!

I'm just trying to figure out what a "major pita" is. :-)

ah, I think I can contribute here... a major pain in the a$$

Oh, duh. Thanks for the translation. (Kids today.) :-)