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Tuscany Itinerary Guidance, Please

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I am planning a 9 day vacation for my husband and I (both in our early 30's) to Tuscany. I would love some insight and/or suggestions on my itinerary. We will be flying in and out of Rome. A little background: We have both been to Rome, Florence, the Amalfi Coast and Lake Como. We absolutely love France, particularly Provence and the French Riviera.

Day 1: Day in Siena, Overnight in Siena
Day 2: Day in Siena, Overnight in Siena
Day 3: Volterra, San Gimignano, Monteriggioni, Overnight in Siena
Day 4: Drive through the scenic Chiantigiana Route, Overnight in Siena
Day 5: Pienza, Monastery of Sant'Anna in Camprena, Tour of LaFoce, Overnight in Pienza
Day 6: Montalcino, Sant' Antimo Abbey, San Quirico, Abbey of Monte Oliveto Maggiore, Overnight in Pienza
Day 7: Montepulciano and Cortona, Overnight in Pienza
Day 8: Assisi, Overnight in Pienza
Day 9: Pitigliano, Orvieto, Overnight in Pienza

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