I am planning 7-8 days in the Florence area with the following destinations I want to see: Florence, Sienna, Pisa/Lucca, Volterra/San Gimignano, and the Val D’Orcia Loop. I would like to try RS’s idea of having a home base and then making day trips out and back, but I think it might be best to pick 3 towns like Lucca, Siena, and Florence? Or maybe a Farmhouse B&B near Volterra instead of Siena? We would use trains as well as a rental car or minibus tours to get from place to place. Does this sound reasonable for the last week of May? I just don’t want to wear my family out since this is only the first half of our Italy vacation! Thanks for any thoughts!
Many will have great suggestions here, but I think Florence is a great base. Beside a lot to do in Florence itself, the train can be taken to most all these destinations. Sienna is easily reached by coach bus from Florence, and the drop you off in town so no hike from the station. We did Lucca and Pisa as a day trip, going to Pisa first, then Lucca on the way back. Ease day, no driving. You won't want a car in Florence, but you can rent one and do any of the day trips. Volterra is 1 hr. 23 min by car or you could do an organized bus tour.
Last year we rented a lovely apartment by the Duomo and enjoyed every minute of it. Florence is very walkable, and a lovely town. There are so many day trip options from Florence, and you definitely do not want a car there. Hopefully Roberto jumps in here. He gave us wonderful suggestions for our last trip. It was our 5th trip there.
Thank you for your thoughts!! While I definitely want to stay in Florence, I also want to stay in an Agriturismi. I’m just having such a hard time figuring out the order of seeing these towns. Right now just from the map it looks the the most straightforward way would be to start in Florence, take a train to Pisa/Lucca, then take a rental car to Volterra/San Gimignano, car to Siena, then return car to Florence and take a train down to Rome.