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Tuscany and Rome Itinerary Questions

Three couples are taking a Viking Ocean cruise in September 2025 from Venice to Rome. After the cruise, we would like to enjoy 4 days in Tuscany and 2 in Rome before we return home. Should we stay in Rome for 2.5 days after our cruise and then travel to Tuscany or the other way around? Also, if we stay in Rome prior to traveling to Tuscany, would it be better to catch our flight from Florence or Rome? And one final question: What is the best way to travel from Rome to Chianti?

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I would first search flights out of Rome, Florence, and Pisa, and see if that makes the decision for you.
Are you planning on renting a car for the Tuscany portion? The flight will determine the car drop off location--after or before Rome.

ETA I just realized you said three couples and not two couples--that means using one car is likely out. Did you have a sense of where you wish to stay (agiturismo or village, etc.)? Will you all be doing everything together? I am trying to parse out the pros and cons of two vehicles versus hiring transfers and drivers. It's that or renting a van.