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Siena, Florence, San Gimignano--Order to visit??

I have 13 days to travel between Venice(3nights) and Rome(3nights) in the first 2 weeks of October. I would like to visit CT, Florence, and Sienna as well. What order would you recommend I visit each place and where should i spent nights? I've read that some prefer to base out of Seinna and do Florence and SG in day trips b/c its cheaper. Any and all suggestions welcome!

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I actually spent a night in San Gimi, it was nice, the crowds go way down, and we stayed in a little room above a store and had a nice dinner. I think the lodging and restaurants came from Rick's guide (I can check to make sure).

It was fun walking around there at night as it was so medieval.

I would say if you can time it right for your itineraary, it is a very pleasant place to spend a night.

I liked driving from town to town and staying in different places for a night or two. Definitely a personal preference think though.