Ciao Kim! First of all, your trip sounds AMAZING!! You'll have to share information with us about the cooking class and let us know how that goes. We are always looking for local experts to recommend to our members!
It sounds like you are the perfect candidate for our free 30-minute travel planning session. @Erin Meadows29 is our resident train expert and would be happy to help you plan this out. You can book a session (absolutely no obligation - this is just a perk we offer our ItaliaPass community members) on her calendar here30. If you decided to purchase, you could book directly with Erin who handles itineraries with our partner brand ItaliaRail.com25, which is directly affiliated with Trenitalia, the national railway in Italy.
In the meantime, however, here are a few considerations/questions:
- Flying into Rome probably makes the most sense in terms of cost and convenience, when you consider the price of the flight over, plus airport transfers once you arrive. What are the factors you're looking at in terms of your decision between Rome and Florence airports?
- Getting from Rome up to Montepulciano by train is rather simple, just one change from Termini. However, being a hill town, on the way up to Venice it does require a bit of back-tracking in order to get out to the main line in Florence first (two changes).
- Does the cooking class host offer transportation to/from the Florence train station and/or Florence airport?
- Does your Venice cruise end elsewhere, or do you need to consider transport from Venice to the airport for your flight out of Italy?