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Florence, Tuscany, Siena????

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Guys, we will be in the Tuscany Region in October. My wife and I spend 4 nights in Florence in the past (loved it, we did day trip to Chianti on a bus trip...) but the other couple we are going with has never been to Italy.

So, my wife and I thought we may change to Siena for our home base this time. Is Siena worth staying 4 nights. We hope to day trip to Montalcino one day and Chianti another. Is that easily done from Siena without a car? Should we consider a local Agritourismo instead of a stay in Siena...

Should we just stay in Florence and use the train to get to Siena, Montalcino, and Chianti?

I would love to find a way to visit Pisa as well...should we only do Montalcino and skip Chianti?

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