We recommend you reach out to a travel agent, we recommend - margaret : https://www.foratravel.com/advisor/margaret-scott - kelly: https://idletimetravel.com/about/ Both have great recommendations to help plan a trip.
Yes, we plan to provide shuttles once a day from florence to cortona september 2,3,4 as well as return on the 6th and 7th. We will reach out as wedding gets closer with exact times. If you want to travel on your own time, there is a local train that runs from Florence to Cortona about every hour - Trenitalia.
We will also plan to provide shuttles from Cortona to our venue Il Falconiere (about 10 min ride)
No, if you’re staying in Cortona, or at Il Falconiere everything is quite accessible and we will provide transportation. That said, if you want to explore Tuscany more freely, renting a car could be a great option.
The plan is to be mostly outdoors, early September in Tuscany is typically warm and sunny during the day, with cooler evenings. We recommend bringing a light layer.