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Tuscany: What day of the week for what city, and hidden gems

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Dear Friends-

We are 2 couples planning a trip to Italy. During part of our trip, we will be staying in Montespertoli for 5 nights, which gives us 4 full days to explore (Sun-Wed). We are planning day trips to Siena, Pisa, and San Gimignano (Florence is covered separately in our itinerary). I have a few questions:

1. Any recommendations on which day of the week to visit the different towns? I read that there is a local market on Wednesday's in Siena and am looking to see if there are other weekly events we should consider.
2. Any recommendations for "hidden gems" in the area? By this, I mean something you experienced in your travels (restaurant, museum, area of town, etc) that wouldn't necessarily be found in the guidebooks.

Thanks in advance for your help.

Dave

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