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Help with Tuscany / Florence portion of trip

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Our trip begins in Rome and ends in Venice. We have 7 days between the two, and plan on going to Tuscany and Florence. We plan on traveling by train, and only using a rental car for the few days we are in Tuscany. Train from Rome to Chiusi and staying in or near Montepulciano. My husband and friend have driven stick shift but haven't done so in years. Will practice with a friend who owns a stick shift currently. Driving will be kept to a minimum in the general area where we are staying. There are 5 of us.

I was in Italy 7 years ago (first and only time) and when in Tuscany stayed near Pienza. Visited there as well as Montalcino, San Quirico, and Bagno Viigoni. Sister in law has spent time in Cortona. Husband, son, and our friend have never been to Italy so have no opinion.

I am thinking of traveling to Chiusi from Rome and arriving by noon or so. Picking up a car and spend that day plus 3 additional days in Tuscany. That allows for spending day of arrival (morning) plus one full day in Florence. That doesn't give us much time in Florence, but I think several days in Tuscany might be needed for rest and relaxation given the rest of the trip will be done in cities.

I am torn between spending 3 1/2 days near Montepulciano and 1 1/2 days in Florence. I would love to check out Montepulciano and don't necessarily care where else I go in that area. So beautiful that I don't mind re-visiting places I've been. I will be seeing Italy through the eyes of my husband and son who have never been there. I know there are some abbeys and small hill towns worth visiting besides the obvious ones I mentioned above.

OR, I could cut southern Tuscany by one day and add it on to Florence. My SIL has suggested visiting San Gimignano. Due to the fact that we don't care to do much driving (5 people and luggage in a car) it makes more sense to do a day trip from Florence if SG is thrown into the mix. And, there are more options for day trips from Florence. The guys could take a train to Pisa (SIL and I have been there) and we could go to SG, for example.

I will discuss more in depth with all in my traveling party, but would appreciate thoughts from Fodorites. We are open to all ideas.

Thanks in advance!

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