Italy, October 2025

I think your timing is good, not too rushed. I haven't been to Siena yet so I can't advise on that part.
My only suggestion would be go from Siena (or Florence) to Sorrento for your nights there, then to Rome, so all your Rome days are at the end and you're not adding another check in/out for just one night.
I can recommend a great private guide in Florence and Milan if you 're interested.

Hi Celeste
Thank you for your input. Yes please, send me the information for the private tour.
Thank you

I think your itinerary looks pretty good and not too rushed.

A few notes:
- Pisa, Lucca and Bologna should be visited from Florence where you're closer than Siena. Lucca and Pisa can be done in a long day loop on the train while Bologna is a good day long trip and is 30 minutes on the fast train.
- Bus is a bit better from Florence to Siena but it's not a deal breaker - train is fine you just need to walk to bus into the town itself since the train station is on the flat.
- Rural Tuscany is difficult without a car - public transportation is spotty - I would arrange winery, town tours with a guide from Siena or resolve to rent a car. (Get an IDP for all drivers before leaving the states.) You can return the car in Siena but will probably end up going through Florence to take the fast train to Rome. Dropping off the car where you rent it skips a drop off charge.

My only general warning would be to not plan too many day trips - but how many is too many is up to you. Be sure you're leaving enough time to see the towns you're staying in before heading off for other places. Florence deserves at least a couple of days on its own and Siena deserves at least one full day but both places will easily fill more. I know the list of things you want to see is large and you have already probably crossed off a bunch of places but rushing around the entire time can leave you filled with logistics and a lack of experiences. Make sure you're spending time in places you're actually going to there to see.

Have a great trip,
=Tod

I sent you a private message.

7: Day 18 Travel to Sorrento. Visit Sorrento for three nights. Explore
Sorrento, Visit Pompeii; Day trip to Cinque; Day trip Atrani (I would
love to visit, Santuario Santa Maria del Bando) Subjections?

Benjamin, if by "Cinque" you meant the Cinque Terre, it's nowhere near Sorrento/Amalfi coast. That's way up north, even further north than Pisa, and not a day trip from this region. Did you confuse it with something else?

Hello. Number 4 on your list. Take the bus (#131R) to Siena it is faster and drops you off inside the walls near the center. From Siena to San Gimignano, you may take a bus (#130). If you have a car, it is an easy drive and much faster and would also allow you to make a stop in Volterra. I would drive to Montepulciano. It is a beautiful drive, and you could stop in Pisa along the way. For each of these trips I would plan a full day. For a cooking class in Siena, we have taken two classes with Costanza Piccolomini. The class is in her home, and she makes it quite fun. (This is not professional school. It is an Italian woman cooking in her home kitchen.) You will make three courses, and all are served with wine (of course!!!) Her information is: [email protected] and phone at +39 339 279 3503. You may also do a "search" on this forum for cooking classes in Siena and you will see other suggestions.

I would drive to Montepulciano. It is a beautiful drive, and you could
stop in Pisa along the way.

Pisa is not on the way from Siena to Montepulciano
Maybe you mean Pienza?

You can take the bus from Siena to Rome and avoid going back thru Florence. Flixbus
But if you haven't booked lodgings yet or can cancel- I would go from Siena all the way to Sorrento- (via train thru Florence-to Naples, etc) then put all Rome nights at end

Hi everyone.
Kathy, you are correct that was a mistake. I was thinking on another place.
Charylm, Thank you very much for the information. I'm sure my wife will love the cooking class. I can also learn few things. ha, ha :)
ChristineH, Thank you again for your input and suggestions. Pisa, we were thinking on taking a day trip by bus or driving and enjoy the area and really take our time to explore.

Pisa from Florence by train is much easier and quicker than from Siena
1 hour by train or bus from Florence
2-3 by bus from Siena, 2 ish by train from Siena with a change

Your itinerary looks awesome! I did a similar trip to Italy last year through https://gowithguide.com/Italy and it was an unforgettable experience. One thing I found helpful was booking some guided tours, especially for winery visits and day trips, takes the stress out of planning and transportation. Also, Pisa is much easier as a day trip from Florence rather than Siena.

Thank you ChristineH. I realized my error in the middle of the night. I meant to say an option to stop by Pienza.