Need suggestions for extra 2 days in Tuscany

Hello deborahstange, and welcome to the forum,

Even in October you will find a decent amount of tourism in many places in Italy. Porto Venere is very small and very touristy as I suspect Cortona is but maybe someone has more experience on the ground in October. Lucca has a fair amount of tourism but also a real, thriving Italian community underneath and might be a good choice, but watch for your proximity to comic-con at the end of October/beginning of November which is crazy.

Pienza - like many of the small, rural Tuscan towns is hard to reach without a car.

Of the places you suggest I think Lucca is closest to what you're looking for but if you want some other places to consider you could think about:
Arezzo - a larger town easily accessible by train from Florence that is a blend of newer city and old town on the hill.
Pistoia - just a town outside Florence on the same train line as Lucca and often considered by people who live in Lucca.
Chiavari/Sestri Levante/Moneglia - there a series of towns on the Liguria coast north of Cinque Terre which are closer to what you describe if you were considering PV.
San Terenzo/Lerici/Tellaro/Sarzana - these are towns on southern side of the Bay of La Spezia across from PV which I found much more interesting. Anywhere on the coast of Italy will have tourism but in this area the tourism is Italians and should be slacking off by October.
Verona is a beautiful city with a cafe culture and things to explore but is somewhat touristy - although much of that tourism is German which makes it feel "European" over hearing a lot of English.
Brescia is a city I enjoyed as a day trip from Verona with a whole series of connected great piazzas, some churches, great Roman ruins and castle on top of hill which will have virtually no tourism.

Keep in mind that less tourism means less English spoken so the more "authentic" you go the fewer accommodations there are so you'll be setting yourself up for more work.

Hope that helps,
=Tod

If you are open to car rental, you have far more options. For two days, I don't know if that is what I would do, but you have to decide that first (I'd do something like Orvieto or Siena by train/bus). Whether coast or inland, a car would expand the options. I have read Portovenere is very popular so maybe not quite what you are looking for, but I loved Lerici.
For a place like no other, southern Tuscany is my spirit place.

Valadelphia is spot on.

Orvieto would be great as there is enough to do for a couple of days and is right in between the train routes between Florence and Rome. Siena is wonderful but a bit harder to get to.

Thank you for your replies. I appreciate it! After reading them and going down the rabbit hole on several sites, I’m “narrowing it” (lol) no car and going to a place which minimizes travel time on our way from Rome to Florence. Thinking Montepulciano, Montelcino, Sienna, Arezzo or Orvieto as a stop for 2 nites. Saw a “Dinner in the Cellar” small group tour on the RS site that sounds fun from Montelcino. Wondering if anyone has experience with that. I’ve been to the first 3 towns yrs ago but only for a few hours in each place.

For Montepulciano and Montalcino, you would want a car. Siena, Arezzo, or Orvieto could be done by bus/train.

Orvieto is lovely and makes the most sense travel-wise.
Arezzo works as well

Montalcino, Montepulciano, Pienza require a car
Lucca is wrong direction

Siena can work but to get to Rome you will go back to Florence first. (or there is a bus Siena to Tiburtina I believe)

I love driving the country roads in Tuscany -- just stay out of the cities! If you want picture perfect postcard views, I'd strongly recommend driving through Val d'Orcia (Pienza, Montalcino, Montepulciano). If possible, try to book a couple of nights at an agriturismo -- if you can find one available for just 2 nights. Definitely rent a car and do day trips.

Hi - we were in Siena in March for a week and it was really, really great. It has a very different feel to either Florence or Rome, largely because Florence defeated Siena centuries ago and not much development took place in Siena after that. The city is a tiny medieval gem. You can get there by bus [131 from the bus station] or train from Florence, and yes if you are then going on to Rome is either direct bus [Flixbus] or local train back to Florence and then high speed rail down to Rome. Have a great time wherever you pick.