A rule of thumb used by many experienced Italy travelers is that changing sleeping locations eats up about half a day, not including the actual travel time between the destinations (this is packing up, getting to the train station, etc). Example: If the station to station train time between sleeping destinations A and B is 2 hours, changing locations eats up 4 hours + the 2 hours of travel = 6 hours, most of your daylight hours in October (when the sun sets earlier than in the summer).
You have 10 days: you mention 3 destinations and then added a 4th, CT. You'll be able to do the math: with 10 days, and if you want to spend x # of days in the locations, and it's y # of changes in location, you run out of days at a certain point, normally before you've seen every destination on your wish list.
One solution is to assume you'll be back. If you're not going to be back, you may be tempted to add more locations, at the cost of less time per location. I think you see where I'm going with this. There's tradeoffs and decisions you'll have to make.
Oh, October is an iffy month in the CT, which is all about the outdoors, which is a function of the weather. Some will post on this thread and tell you they had great weather in October in the CT; others who didn't have such a happy experience with the Oct weather in the CT probably won't post because they don't want to rain on your parade.
This link may help you: help with itineraries & travel times in Italy
Get back to us after you think this over a bit.
