9 days in Italy, asking for itinerary recommendations

What part of October, early, middle or late? Reason I ask is: Cinque Terre is all about be out of doors but that is weather dependent and October is a transition month weather-wise.

You can easily spend 9 days in Firenze and the rest of Tuscany. I'd split it between Firenze and an agriturismo in southern Tuscany, maybe around Montepulciano. From there you can day trip to wineries, other small towns, even into Umbria if you like as long as you have a car. Take the train to Firenze form Milano, rent a car, "do" the agriturismo and hill-towns, then return the car, see Firenze and return to Milano by train. October can be chancy for the CT. If early Oct, fine, but after about the 10th I'd worry about weather.

You could train from Milan to the CT when you land. Spend 2 nights in the CT. Take the train to LaSpezia and rent a car while you visit Tuscany for 5 nights. You can stay someplace central like an agristourimo around the Siena area and day trip to wine country of Chianti, Montalinco and Montepulicano. Drop your car off when done in Florence and take the high speed train to Milan to spend that day and nitght in Milan for your flight

In between Milan and Tuscany, there are a lot of great places in Lombardy and Emilia-Romagna. You'll need a book other than Rick's to learn about these, but particularly for a second visit, you may want to investigate Cremona, Mantova, Bergamo, Parma, Ferrara, Modena, etc. You'll notice I didn't put Bologna on that list; it's my least favorite place in Italy, but others love it, so you should look into that as well.

With 9 days you could see a decent amount. I would head to Florence and from there you can spend a few days just on Florence but then take day trips to places like Lucca or stop there on your way to the Cinque Terre where you would want at least two nights so that you have one full day but three nights can be better. For visiting Tuscany you can either use Florence as a home base or stay in the countryside. Since you mentioned you are open to renting a car you might want to find a home base around Montepulciano or Sienna (these two are in a good location and give you a little more of an option to visit some of Umbria too). You may want to watch some of Rick's programs to get a visual on what each area offers. Once you have a better idea of what caught your eye Rick gives his updated travel tips and recommendations in his guidebooks. Happy Travels!