Italy Sept. 20 - Oct. 5, 2024

Welcome to the forum and happy Anniversary!

You will really need a car for those Tuscany locations
Not served well or at all by train

Why only 1 night in Rome?
I’d drop all the other outlying places and add time there

Or just fly home from Florence/no need to go to Rome

Looks like 5 nights in Milan and a day trip every day-that will get tiring
And you’ve spent hardly any time at all in Milan itself.

Unpopular answer but we don't have much interest in Rome. My dream visits lie elsewhere. We don't know if we will be back but if we do someday, we will spend time in southern Italy which I had to leave out of this trip. It's just a choice we have both decided on. We like to explore and be on the move. See what we like, what we would come back and spend more time on or skip.

Good to know about the car. Will look into a car rental out of Florence.

coming from Toronto, we can't get a direct flight into Florence, it's costs more to fly for us into Florence or Naples, etc. flying in and out of different locations. Too much time in a layover to other countries. We had a travel agent very well versed in Italy search and book the flights for us.

You might want to review your old post here:

https://community.ricksteves.com/travel-forum/italy/italy-planning-questions-advice-tips

Specifically for advice on car rental/driving

Thanks, was so long ago didn't realize they don't get deleted after some period of time.

It feels rushed to me, with more daytrips than I would find enjoyable. By my count you have 14 nights.? Personally, if you have the ability to change your first flight I would go to Milan even with a stop-over. I'm sure British Airways has that. Because otherwise you are flying into Rome and then taking a train from the airport to Termini, the train station in Rome, and then another on to Milan. It will be a very long day anyways.
Trying to respect the places you want to go, I would suggest
Milan 4- night with only two day trips ( Como and the bernina express?)
Verona 2 night, -skip Genoa
Florence 2 night
Stay in Siena - your best chance to see some of those towns is by bus if you don't want to rent a car ( 4 night), and it is a bit of a hub. ( Someone else may know of a better one?)
Rome your last 2 nights

Oh!
Missed that you were flying in and out of Rome!

That trip from Rome to Milan adds a whole other issue
I suggest you add up all the time you will spend on trains, and time/transit/cost getting to and from stations during your first 5 days if you keep all those day trips
Be brutally honest and I think you’ll see what we mean about it being too much

Do your tickets allow for changes so you can fly into Milan and out of Rome or vice vs?
The name of Rome’s airport train station is Fiumicino Aeroporto: https://www.trenitalia.com/en.html. Take a train from the airport to Rome’s Termini station where you’ll need to transfer to Milan’s central station. From Rome Termini take the fast train to Milano Centrale (3h 15m).
Sep 23 – when you get off the train in Varenna take the ferry to Bellagio and explore Bellagio first. Afterwards hang out in Varenna for a while before taking the train back to Milan’s central station.
Sep 24 – Bologna is not a day trip from Milan but Verona is. To appreciate Bologna, you need to spend the night.
Sep 27 – Take the train from Milano Centrale to Firenze (Florence) SM Novella station.
Sep 28 – if you visit the Uffizi Gallery in Florence buy tickets two-months out to guarantee a reservation.
Sep 29 – take a direct bus from Florence to Siena (1h 15m) and sleep in Siena’s old town.
Sep 30 – rent a car in Siena and drive to Pienza’s old town along the Val d’Orcia: https://lovefromtuscany.com/scenic-drives-in-tuscany/. It’s a memorable drive. After you visit Pienza go to Montepulciano.
Oct 1 – drive to San Gimignano.
Oct 2 – drive to Cortona.

I wouldn't use Rome2Rio for information on transportation schedules, fares or frequencies. It has been shown to be very inaccurate quite often. The most I use it for these days is to find (one hopes) the name of the bus company operating on a particular route. Often there's also a link to the company's website, which is useful.

For information on the trains, refer to the websites of the companies that operate them: www.trenitalia.com and www.italotreno.it .

Important: The Bernina Express train route runs from Chur to Tirano. If you only buy tickets between Tirano and St. Moritz, you will be missing most of the trip.

I would look again into your flights. I just checked on google flights and you could fly from Toronto into Milan and out of Florence to Toronto with just one stop and layovers of about 2 hours.