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Tuscan day trip stops

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Ok. So my husband and I have a wonderful Italian getaway planned for our 20 anniversary. We have never been before and are planning to take the train from Florence to Siena as we have an overnight stay and winery tour scheduled there . The following morning we will have car/ driver to get us to Rome. We can take our time as our only plans for that day are to get from Siena to Rome. I would love some thoughts on possible stops along the way. We have looked at maybe doing Montepulciano and Orvieto. That looks reasonable on a map, but is there something else we should do instead? We also considered going to Tivoli ( it appears to be kind of on the way.) Any great suggestions on stops, food, etc would be appreciated.

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