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5 Days on Umbria and Tuscany border. Difficult choices. Please help!

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We will have 5 full days in Paciano. Arrive Sunday 23 June afternoon from Parma and leave Saturday 29 June for Matera. I need help to put together itineraries for Monday to Friday. The more I do research, the more I get confused. So many beautiful places, I realise we will have to choose. Here are the places we would like to see. Can you please help me to group them into 1 day itineraries to save time. Please add if I missed something or take them from the list. Thank you!!
Pisa, Cortona, Arezzo, Siena, Voltera, Montalcino, Assisi, Spello, Orvieto, Spoletto, Casiglione del Lago, Perugia, Chiusi, San Gimignano, Pienza, Todi, Terni, Montefalco, Urbino ... never ending list!! We would also like to taste some fine wine.

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