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Help with 4 Nights in Tuscany

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Hi all. Please pardon the long post---it reflects the struggles I'm having with my planning. Wife and I will have 4 nights in Tuscany sandwiched between Venice and Rome. It is our first trip to Italy. We plan to take a morning train to Florence on day 1, and spend at least that day and the next day in Florence. We are not huge Italian art lovers (other than architecture and some sculpture). We both love wine, and I'm not planning on renting a car (for related reasons). We're not interested in Pisa or Lucca on this trip; we are considering doing a day trip to Siena and/or SG, and would like to do at least one wine tasting. We are open to guided tours (prefer smaller ones), and I know we could hit Chianti, Siena and SG in one long day. That would allow us to stay in Florence the whole time, which many people seem to recommend. Here's the dilemma---I would also very much like to spend a day in the Val d'orcia, seeing some or all of Montepulciano, Montalcino and Pienza. Do you think it would be too much to do 2 day trips from Florence, with one all the way down to Val d'orcia? Would it be preferable to split the nights between Florence and Siena (keeping in mind that we need to get to Rome in the morning on the final day in Tuscany)? For instance, find a tour/driver to take us to Chianti/SG/Siena, and leave us in Siena; then, take a tour to Val d'orcia out of Siena?

I know that no matter what it's not enough time in any one place, but it's likely we won't get back anytime soon and I'd like to make the most of it. But I don't want to wear us out, either.

Any creative suggestions are welcome! Thank you in advance.

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