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Florence to Rome. Day and 1/2 tuscan detour

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We will be in Italy in the fall and had initially planned to train it from Florence to Rome, but we would really love to see some of Tuscamy as well. Problem is we are short on time so it would be more of a drive by. I thought we could take the express bus to Siena, stay the night, and then use a service to drive us from there to Rome stopping in Orvieto and Montepulciano along the way. Oh, of course we would like to have a winery tour and have no idea where to stay. Is this crazy? Have any thoughts other than " what are you thinking?". I know it's a short time period, but we have no day trips planned from Rome. We will see the Vatican and have a third tier tour of the Colosseum. The rest is free time to explore.

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