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7 nights in Tuscany/Umbria

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We are two friends traveling to Tuscany/Umbria in late April for a total of seven days. We have reservations in Florence for the week but are considering spending a night or two in Umbria so as to visit Assisi, Gubbio and Arezzo. We don't plan on renting a car. Thought of doing a day trip from Florence to Assisi and Gubbio and decided against it because of the cost (about $500). Instead we are considering taking the train to assisi spending a night there and renting a taxi to drive us to Gubbio and from there to Arezzo. Questions - is it easy to get a taxi for this purpose in Assisi - we are told the lines at the train station are very long. Also, would it cost a great deal to rent the taxi?
The remaining nights we are struggling with trying to fit in San G; Siena, Volterra, Lucca and Chianti. Any suggestions on how to make all this work would be most appreciated. We have signed up for a half day cooking class in Chianti area for one of the days.

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