italy in mid october

If I was trying this (I wouldn't in only 9 nights), I'd go straight to Florence. Then to Positano (train to Naples, Circumvesuviana towards Sorrento, then bus or taxi to Positano). And end up the last 3 nights in Rome. That way you don't have to worry about getting to your departure flight on time.

There is no easy direct travel to Positano - everything requires multiple modes of transport. Although, if you get there while the ferries are still running, you could train from Florence to Salerno and then a ferry to Positano (or taxi).

For me, a Minnesota gal, Positano was warm enough in October for dresses and skirts when it wasn't raining. We had an entire day of rain in Amalfi. We also had an entire day of rain in Florence, but were able to spend the day in the Uffizi and the Academia. It was harder to occupy ourselves in Amalfi in the rain. It is my understanding that fall is a rainier time of year in Italy and it certainly was our experience. Since Amalfi is the most weather dependent, I'd probably go there first.

I honestly think your itinerary is a bit much in 9 days, especially since you are flying in and out of Rome. You will lose at least 1 1/2 days just moving locations. It is really hard to decide among those 3 great locations.

Have you been to CT? We honestly liked Amalfi better than CT, but CT is more doable with Florence and Rome, IMO.

There's no easy way to get to Positano from either place. The simpler is probably train to Salerno (direct train about 4 hours), then take a bus to Amalfi (1.25 hrs) and another to Positano (45 minutes or more). Or if the ferries are still running, you may find one that goes from Salerno to Positano. It's an easy 10 minute walk from the train to the ferry pier in Salerno. Back to Rome would be the same, just a shorter train ride. As you can see, you will use up the better part of a day getting to Positano and another going to Rome. That's just too much wasted time on such a short trip.

You said 9 days, but is it really? To have 9 full days in Italy you'd need 10 nights. Is that what you've planned?

Thank you all for your fantastic suggestions! Ive decided that adding Positano might be a too ambitious. I do like the idea of CT. Now I’m thinking of focusing my stay in Florence ( with day trips towns in Tuscany), Cinque Terra, and Rome.

Would you recommend renting a car to get around CT/Tuscany?
Thank you

Dani, I would not rent a car for CT. Plus, with the cost of rental cars of late, I'd really restrict the use of rental cars to when you really need it. Depending on how you structure your trip, you may want a car for rural Tuscany.

Would you recommend renting a car to get around CT/Tuscany?

A car in CT is a detriment.

You mention '3 days' at each location. Does that mean you are there 4 nights to give you 3 full days or are you meaning 3 nights giving you no more than 2.5 days at each locale?

If you are flying in/out of Rome, put your Rome days at the end of the trip to simplify your departure.

I get the sense you are trying to put a size 9 foot into a size 8 shoe, with all the places you mention planning to do. You might be able to do it, but it will hurt.

There is validity to the 'less is more' mindset.

Depends on when in October.

I spent time in Castellabate (about 34 miles straight across the Gulf of Policastro from Positano) several times in early to mid October, and the weather was always very pleasant very much shorts and tee shirt weather - and the sea warm enough to swim despite the stange looks we got from the locals.

We are doing this exact thing Oct 17-26. Flying into Florence we will arrive early morning of the 18. Staying in Florence 3 nights in Rome 3 nights and Positano 2 nights. Very doable!
You won’t have 3 nights to spend each place as your whole first day is full of flying at least ours is and we leave the US around noon the 17th. You can’t plan for anything that first day or night.