Late September Itinerary Advice

I don’t see a flight from Trieste to Florence. Train is 4 h.
Parking is extremely scarce in CT; popular options are to park in a garage in La Spezia or stay in Levanto at a hotel with parking.

From a quick search I only see nonstop flights to Rome from Trieste within Italy. If you are limited to train making it to CT will be an all day adventure. I know it's 7-8+ from door to door from Venice to CT and Trieste can't be any better is probably longer.

With as little time as you were planning on spending there I can't imagine the trip is worth it. Why not recalibrate and look at a lake side location on Lago d'Iseo or Garda? It's 3-4 hours to Verona and the lakes are reachable from there. Or stay in Verona itself as it is on the fast train line to Florence and then onto Siena and southern Tuscany.

Siena deserves at least an entire day on its own and then rent a car from there and rent a car from there and continue exploring.
The end of your trip depends on where you fly home from.

My $.02,
=Tod

Yes - sorry I forgot to add that the flight to Florence from Trieste stops/connects in Rome.

Rome is about the same travel time to CT as Florence, if that helps. Going all the way to Florence adds time to your journey to CT.

Connecting a flight through Rome to get to Florence from Trieste to get to CT for one night?
I stand by my recommendation.

-Tod

Well it was 2 nights in CT, in the outline I provided above. Looking for feedback on the whole thing if possible

At what time do you get into CT? I’m guessing pretty late? If late, you really have 1 day in CT, 1.5 days in Siena, 2.5 in heart of Tuscany and 1.5 days in Florence. That’s too much time moving around. Maybe drop one place, probable CT and leave it for another trip. Can you drive from Trieste to La Spezia and drop the car off there instead of flying to Rome, then Florence and then train to CT?

I think it’s best to drop CT from this trip.

I do see that you are going to spend 2 nights - one full day - in CT from your schedule. I normally try not to give advice on CT since I was lucky enough to visit it 20+ years ago back when what people are seeking actually seemed to be there. But I honestly don't see how the CT matches your list of wants enough to merit two flights plus 3 more hours of travel logistics to get there. CT in September is a mini-Amalfi Coast filled with day trippers from Florence and also potentially from cruise ships docked in both La Spezia and Livorno. I personally don't see the appeal to spending a entire day of travel to get there for one day and then spending one full day and then traveling 4-5 hours the following day to get to Siena.

I personally think this is too much travel time out of your limited schedule to spend on just moving around. If CT for several days was your goal then I would feel differently but you have a full day there at the cost of a full day of travel. If your goal is to experience rural Tuscany then I would concentrate on that and add the CT day and some of the CT to Siena time to the Tuscan schedule instead. Either make it to Florence the first night or make a one night stop most of the way there (say Verona or Bologna) and then push onto Siena the next day. Check the time of flying to Rome and training to Florence versus taking another flight and just training directly to Florence as well. For moving around major cities the fast train is often faster than the flight plus the wait times for internal Italian travel.

Spend at least full day in Siena and then rent a car and the concentrate several days in southern Tuscany. The towns of Pienza, Montepulciano, Montalcino, San Quirico d'Orcia and other small towns are all clustered together for relatively easy driving. Consider the car when making reservations and be sure to understand ZTLs and parking before you arrive. Add at least 25% to Google drive times for rural driving.

If you really want to experience Tuscan culture you need to slow down enough to feel at least a bit of the schedule that works on agriculture time and seasons versus hectic days. The "clock" in Siena's El Campo is actually a calendar not a clock - that's a hint at the slower pace of life. I think a languid spritz or Negroni or two on El Campo - even better if you can manage one of the small balconies - as the sun sets is a peak Italian moment. It's not flashy or exciting but it is just a series of slow moments with nothing else to do and no time pressure just your company and the slow fading of the day.

You could drop the car back in Siena and train to Florence for your final night before flying home. There is a tram from the train station to the airport but chances are a taxi from your hotel is probably the best bet.

As I said I try not to give advice on the CT in general. I had a coworker who really wanted to go and went as a cruise excursion a few years ago and she loved it. I did my best to prepare her for the crowds and - in retrospect - I'm glad I held my tongue and didn't tell her not to go. So this is just my opinion and only you are going to have your vacation experience - not me - so it's completely up to you.

My $,02,
=Tod