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Car rental pickup Siena or Florence

Hi, we're a family of four going to Italy this summer. After traveling from Venice to Florence, I am still debating where to pick a rental car. My first thought is to taxi from our hotel in Florence (Hotel Casci) to the airport where everyone says it's easy to get out of Florence. Then drive to Siena and park the car there while sightseeing before leaving in late afternoon toward Montpulciano where I reserved a week at the Politians. The cons with this plan is that I have to find a parking space in Siena and pay for the space ( about euro30?)
The other option is to take the Sita Bus from Florence Train Station(close to Hotel Casci) and take the bus to Siena and rent the car there. This is going to be a on a Monday ,I am aassuming the car rental pickup place is open until 5 or 6pm? I guess I'll have to check with autoeurope.
The pro with this choice is that i don't have to worry about the car while we're touring Siena
the con is what to do with the luggage? I guess I can find someplace to store them,any suggestions? and I read that picking up the car in Siena is much easier.
Another option is to just pickup the car in Florence and drive straight to Montepulciano (where we'll be for 7 nights) and do Siena another day. Thanks i advance for all your help. Love this forum!

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